Survey the District: How to Come Clean After Faking It

Dear Date the District,

I’ve been with my boyfriend for about 6 months now, and I’ve faked orgasms with him every time we’ve had sex. It’s not that he’s bad—I’ve just never had one before, and I’ve always been too embarrassed to tell the guys I’m with. I feel totally comfortable with my current boyfriend, and I’d really like to try coming for real with him. The problem is, how do I tell him I’ve been lying for the past six months?

Female orgasms are a sensitive subject. In the absence of any physical proof, guys are forced to rely on their partners for feedback, and fake orgasms are a huge blow to their egos.

Faking an orgasm is a huge breach of trust, because it’s betraying people in an area in which they usually feel pretty vulnerable: sex. Guys usually assume that women only fake it when it’s really bad, and girls sometimes feel like they have to fake it, even if they’re enjoying it, to make their partner feel adequate.

Coming clean can be embarrassing and difficult, and how you decide to do it depends on where you are in your relationship. If you think he’ll take it well, tell the truth. But if you’re worried it might make him feel incredibly sexually insecure (e.g., he seems to get a huge self-esteem boost from getting you off), there are still a few ways to work on orgasming without telling the whole truth.

If you’ve been faking it during penetration, tell him you’ve never had a clitoral orgasm, and ask him to work with you on that. Tell him he’ll need to be patient, but that it’s really important to you, and something you’ve been wondering about for years.

If you’re faking it when he goes down on you, tell him you want to find your g-spot.

If you’ve started taking medication, you could blame it on that. Tell him your new birth control means you’re going to need to work a little harder to get you back in the saddle, but that your doctor really wants you to try to make this brand work.

Because you’ve never come before, you’re probably best off having him spend more time eating you out. Tell him you want it to last longer than usual, and that you’re going to hold back and make him work harder to get you off.

You could also try something like this, “I always thought I was coming with you, but the other day in the shower, I was touching myself, and it was like this explosion. Like, with you, it always felt really good, but I think maybe this was my first ever orgasm—I was like squirting and everything. I want to get there again—and I want you to do it for me.”

At the end of the day, though, if you love and trust him, you should be able to come clean and work through your sexual exaggeration. He’s obviously doing something right if you’ve been together this long, and make sure he knows how good makes you feel in bed before you tell him your performances might have been a little less than authentic.

Cheating In Your 20s

Fidelity is always murky in the 20-something dating scene.

When you’re not quite sure if you’re together and even less certain that he’s the one, it’s tempting to see what else is out there.

But there’s a fine line between keeping an eye out and cheating—you don’t even necessarily have to kiss someone to betray your partner. We’re not going to spell it out, because sometimes you can have drunken makeouts that do less damage than a heart-to-heart.

The problem with cheating is not less that it hurts your partner, and more that it’s bad for you.

The difference between a cheater and someone who’s just found someone else, especially at our age, is that the cheater often still cares about the boyfriend she dicks over. If she were really just bored and ready to move on, she’d break things off, but she doesn’t, because she’s not.

This creates a situation where the cheater is consistently lying to one of the people in her life that she cares about the most. And this is going to fuck with you more in the long run.

When your closest relationships are mired by lies and deception, they start to be less fulfilling for you. You hate yourself for what you’re doing, the other person has no idea, and it just spirals downwards.

But cheating is often so easy to justify. You blame it on the other person’s busy work schedule, his snoring, whatever. It’s never about you.

But if you stop to think about it, you’re probably cheating to fill a void you feel your relationship. Maybe you feel like he’s not paying attention to you. Or you’re worried he won’t stick around and you feel like you’re hedging your bets.

It’s important to evaluate these concerns. Is he really neglecting you to the point that you always feel shitty? Or are your expectations unrealistic in light of a 60-hour workweek? Do you two seem to be drifting apart? Is the relationship salvageable?

Once you’ve figured it out, it’s time to take action. We’re not saying you should tell him, or even sit down and have a heart-to-heart. But you probably should either break up or stop cheating.

So many people think things will be different when they “find the one” or settle down. But if you only know how to be unfaithful in a relationship, how is the mere presence of one person going to undo a lifetime’s worth of bad habits?

To be clear: cheating is not a moral failure on your part. And though the guilt that comes with it often attaches itself to the person you’ve betrayed, the one who’s hurt most is the cheater.

Monogamous relationships are practice for when you do want to settle down. Even if you think you never will, at the very least, they encourage healthy, mutually beneficial interpersonal relationships. 

Unwelcome Blasts from Your Sexual Past

When it comes to exes, there’s always one type you’re almost guaranteed to hear from in the future: the ones you never really dated in the first place.

These are the guys that blew you off. They’re the ones you hooked up with on Halloween, the ones who took you out for a few dinners, the ones who kept canceling plans or forgetting to call you back, and the ones who, when you look back, you can’t quite remember how or why it ended.

They always try to reenter your life at the most inopportune moments. Maybe you’re seeing someone new, having a bad week, or looking for a new job, and suddenly there’s a text, an email, or, in the rarest of cases, a phone call that hijacks all your focus.

First things first: you’re allowed to feel smug. You’re holding proof that he thought about you at least once, and he’s given you the upper hand.

But that’s probably because he’s 99 percent sure you’re going to throw it away.

You can still gloat, but realize that he’s almost certainly not texting you because he’s realized the error of his ways. If he’s left a voicemail apologizing profusely and begging for another chance, that’s one thing, but if you just got a text that said, “what up”, don’t start picking out your wedding dress.

So what should you do?

Nothing.

The temptation is to bitch him out or brag about your new (and potentially nonexistent) boyfriend, but the second you do that, he’s holding the power and you’re feeling like shit.

We know: you don’t want to be rude. But chances are, he probably didn’t bother much with manners with you. And besides, you don’t owe him anything.

As soon as you say, “Sorry, I have a boyfriend,” you’re giving him the chance not to respond. And then you’ll be checking your phone every 5 minutes, making your friends text you to make sure your texts are working, until finally you can’t take the suspense and text him something really eloquent, like “????”.

But if you don’t respond, he’ll be the one squirming, wondering if you got his message, and why you’re not answering.

So let it go.

It’s tempting to use this whole one-sided-on-his-part exchange to help you move on. And chances are, it’ll make you feel at least a little better.

But realize that the most effective path forward shouldn’t involve him. If you can’t get over a guy until he shows a little more interest, you’re going to waste a lot of time waiting for revenge from guys who are updateable to begin with.

The less you can care about the whole thing, the better.

Monday News Roundup: Where Have The Good Men Gone?

The Wall Street Journal recently ran an article about why a good man is hard to find.

We’ll let that one sink in for a second.

The point is basically that young adults are settling down later and later and that women tend to be more mature than men of the same age.

Profundity aside, the article finds its way to a scary answer to the question it lays out in the title. Today’s young men, the article argues, are lazy, immature, and directionless because their female counterparts are too successful.

It's been an almost universal rule of civilization that girls became women simply by reaching physical maturity, but boys had to pass a test. They needed to demonstrate courage, physical prowess or mastery of the necessary skills. The goal was to prove their competence as protectors and providers. Today, however, with women moving ahead in our advanced economy, husbands and fathers are now optional, and the qualities of character men once needed to play their roles—fortitude, stoicism, courage, fidelity—are obsolete, even a little embarrassing.

This conclusion comes after the author spends half the article arguing that today’s middle-class, college educated men and women spend their 20s adrift, trying to find their lives’ callings. Men, she argues, get stuck because of things like Comedy Central, which appeal to their childish urges and prevent them from moving on.

Sure, there’s no female equivalent of Judd Apatow. But to argue that his movies are creating an ethos rather than reflecting one is a little far-fetched. Her argument, taken to its logical conclusion, seems to suggest that the only reason women aren’t investing in 40-foot bongs is that pop culture has yet to idolize the character of the lazy woman.

Somehow, we doubt that’s all there is to it.

It’s hard to argue that the average 26-year-old man is as serious and career-oriented as a woman of his age. But what does that mean for the women?

The WSJ doesn’t offer an answer. The most obvious would probably be to encourage women to date older men. But guys don’t have a magical settle-down hormone that kicks in when they hit 30. And even if they did, it’s not always easy to know what maturity looks like.

A lot of otherwise smart, career-oriented men love movies like Stepbrothers, despite the fact the “best” scene is no more (or less) than a pair of balls.

And there are some fratty bros who can talk your ear off about Cormac McCarthy in a way that makes it seem like they’ve got more figured out than they actually do.

The fact of the matter is, a guy isn’t going to “settle down” until he finds a woman who behaves in a way that makes him want to lock it down. And if we could teach you how to do that in one blog post, we’d be rich.

But maturity is more than just buying a ring. It’s about remembering to call and engaging in interesting conversation and maintaining friendships that don’t revolve around sex and/or partying. And these are things you can—and should—screen for.

A big indication, as much as we hate to say it, is how he spends his free time.

Guys who live for getting wasted on Friday and Saturday nights might be fun to be around, but they’re probably not as mature as the ones who get up for Sunday morning tennis lessons. And while there’s nothing wrong with the occasional Big Lebowski game, guys with daily drug habits probably have some growing up to do.

Excessive boys nights are a bad sign. Platonic female friends are a good one.

Part of it depends on where you are too. If you have a season pass to the Opera and he measures seasons in kickball, you’re probably on different developmental levels.

But the solution definitely isn’t for women to take a step backwards. It’s for us to keep an eye out for the men who have less growing up to do.

How to Be Sexy Part 2

Yesterday, we talked about ways to sex up your first impression. Today, we’re going to go over one simple tip for leaving a lasting impression on men: physical contact.

No one likes to have his personal space invaded, but a little strategic touching can amp up the sexual chemistry he feels whenever you’re in the room.

The key is subtlety. Don’t grab his crotch after you shake his hand. Start of slowly, and if you sense any discomfort, back off. If he pulls back, angles his body away from you, crosses his arms in front of him, or does anything else that seems designed to minimize physical contact, stop.

Start with his arm. When he says something funny, rest your hand on his forearm while you laugh, but pull it back as soon as you’re done. If you’re standing up and need to maneuver around him, put your hand on his back or shoulder to gently nudge him out of the way. If you’re introducing him to someone else, put your hand on his bicep when you say, “This is Mark.”

The goal is to work your way up to ONE thigh-grab towards the end of the night. But you can’t grab his upper leg, lower your voice, and say something like, “Wanna come back to my place?” You have to briefly rest your hand on his leg while saying something totally innocent and desexualized, like, “It was really great meeting you!” or “Let’s talk more about this next time.” Keep your tone naïve and earnest. Everything but the physical contact should be devoid of all sexual connotations. Don’t lean in close, arch your eyebrows, or pull out your best pouty face. Touch him for a second, and then pull back.

When it comes to touching, less is more, but the more physical contact you can make without his noticing, the more lasting the impression you’ll leave.

How to Be Sexy

It’s easy to stand in a mirror and criticize your looks. For the most part, you can’t change what you’re born with, and you only have to step outside to see women whose bone structures and skin seem proof that they won the ovarian lottery.

But sexual attraction often comes down to the difference between “hot” and “sexy.” A hot girl might have blonde hair, giant boobs, and a perfectly symmetrical face, but if she wears it all with bad posture and unflattering clothes, it’s going to negate a lot of what she has going for her. A sexy woman, on the other hand, might have a plain face, but she knows how to work it.

You can be hot without being sexy, and sexy without being hot. But, given the choice, most guys would pick sexy over Barbie.

Being sexy is, for the most part, intangible. It encompasses things like confidence and sexuality that are too complicated to spell out in a single blog post.

But there are things you can do to up your sexyness factor, no matter what you were born with.

The single most tangible factor that determines sex appeal is probably the body. This doesn’t mean an emaciated, skeletal frame buried in layers of baggy clothing, but it does mean a little bit of muscle definition in your legs and butt.

We’re not saying you all need to rush out and join a gym—it could be as simple as trying to use your legs as a method of transportation (walking and biking instead of taking the Metro) or taking a yoga class once a week. And, actually, the point of getting in shape is not to get down to your birth weight, but to give you more body confidence. Size matters a lot less than how you carry yourself—we’ve posted a million times about how guys can’t tell the difference between a size 2 and a size 6, and don’t care if you seem like you’re into it.

It’s also important to realize that curvy hips and thighs are like catnip to most guys. It’s probably a biological thing (it makes you look more fertile/better at bearing children). If you’ve got it, flaunt it with tight jeans (NOT leggings, which give even the most toned women camel toe) instead of covering it up with baggy sweaters.

Carry yourself well. That means good posture at all times—shoulders back, chin up, chest out. When you walk, let the movement emanate from your hips. Buy a good push-up bra, and wear it. Practice composure—don’t fidget with your fingers, bite your nails, or play with your hair.

When you’re shopping, opt for flattering clothes over trendy styles. Throw away your Uggs and invest in a good pair of heels you can actually walk in. The heel should be thin, not chunky, and if you’re really teetering, go for boots—they’re easier.

Skirts and dresses always make you look more feminine and hide the areas where unwanted fat tends to hang out (like your lower abdomen). A good pair of black tights will elongate your legs and make them look thin (as will the heels).

Start taking care of your skin. This means investing in high-quality cleanser, toner, and moisturizer—probably a step up from what you’d find at a drug store. Get someone you trust to pick out the best makeup for your coloring. Your friend who always looks naturally flawless is probably the best option—chances are, she’s wearing three layers of foundation. If none of your friends has an entire closet devoted to beauty products, go to a makeup counter at a department store. Avoid Sephora—the “cosmetic specialists” there seem to have minimal training and maximal interest in blue eye shadow.

Get up early and start actually getting dressed in the morning. Shave your legs—even if no one’s going to see them. Put on makeup and floss. Again, this is less about how you look and more about how you carry yourself when you know your legs are a smooth as a newborn baby’s.

At the end of the day, looking sexy is a lot of work, and for some people, it might not be worth the investment.

But if you’re with us so far, come back tomorrow (and the day after) for more tips on projecting a sensual, sexual persona. 

How to Give a Great Handjob

First of all, we’d like to apologize to our loyal readers for our recent hiatus. We’ve been doing some traveling, but hopefully we’re back to a more normal schedule now. And to all of our Chinese readers, 新年快乐！

The handjob is the oft-undervalued cousin of the blowjob, which, as we’ve discussed in a previous post, is not complete without a well-lubricated handjob.

Most women don’t give enough handjobs. When the going gets soft, most girls are apt to reach for the problem with their mouths, and when it’s time for the warm up, we give what we want to receive.

But a well-placed handjob can be just as good, if not better, than a blowjob—mainly because both parties are more apt to be really into it. Your hands last a lot longer than your mouth, and you don’t have to worry about gagging.

Handjobs are great for couples that like to spice things up in more public places. Pull him into a bathroom or an alley and give him a taste of what’s going to happen when he gets back to your place. But they’re also great for foreplay, waking him up on a Saturday morning, or getting him to run out and get you Chipotle.

The best handjobs come from the women who give them for a living—happy-ending masseuses. (They have, after all, had the most practice.) We surveyed the men we met on our vacation to figure out what they’re doing right—and what you might be missing.

1. Lubrication. We can’t stress this enough. Use saliva, lube, lotion—whatever you can to grease your palms. The point of handjobs (and blowjobs) is to recreate the sensations of a warm, wet vagina, and dry hands will only hold you back in that department. The more lube, the better.

2. Consistency. A classic handjob mistake is rushing out of the gate. When you start pumping at 50 mph, you’re going to lose momentum after a few minutes. When you’re giving a handjob, you never want to loose speed. It’s a huge letdown for the guy, and if you have to stop, you’re basically restarting from scratch. It’s better to start slow and gradually accelerate. You actually don’t need to speed up until he’s about to come—it’s more important to maintain a consistent speed throughout. So start with something you can sustain, and amp it up at the end.

3. Firm grip. Your grip should be as tight as possible while still allowing you to move up and down the shaft. Squeeze his penis extra hard at the bottom. You’re creating a seal, and it should be as tight as possible. Don’t worry about hurting him—if it’s too much, he’ll tell you.

4. Build up to it. If you go straight into it, it won’t be as rewarding as if you create anticipation. For most guys, the inner thighs are particularly sensitive. Trace the inside of his legs with your tongue or fingers. Gently stroke the balls and taint. Don’t go on for too long, but the more you keep him guessing, the better.

5. Do things he can’t do to himself. Push his balls up between his shaft—take his balls in the heel of your palm with the tips of your fingers facing up. Gently push upwards so that his balls straddle his penis. Stroke his balls with the tips of your fingers. Rotate your grip so that your fingers are on the front of his shaft. Cup your hand and place it over the head of his penis so that when you’re thrusting up, it hits your palm—it recreates the sensation of hitting the tightest, deepest part of your vagina.

6. Aim carefully. Most guys don’t enjoy coming all over themselves, so when he’s about to blow, aim out. Don’t let him come all over his stomach, and minimize the amount of semen on his body. If you’re into it, tell him to come on your face—it’s not as bad as it sounds, it’s pretty easy to clean up, and it’ll be a huge turn-on for him.

Send Us Your Dating Horror Stories

It's almost that time of year (i.e., Valentine's Day), and we'd like to get a head start on Gawker by collecting your dating horror stories. In the name of catharsis, send your pick-up lines, walks of shame, and bad decisions to datethedistrict@gmail.com--best ones get thrown up on the blog throughout the month.

To get you started, we're setting the bar high with this story from Hey Lady.

And if you're more in the mood for happy endings, don't forget to send in your matchmaking profiles.

Don't Put Too Much Stock in a Profile Picture

Online dating profiles are hotbeds of superficiality.

The whole page revolves around the photos, and even the most open-minded users usually check the physical appearance before they read any text.

This kind of browsing doesn’t make you a bad person—after all, attraction/chemistry/whatever you want to call it is mostly physical.

But it does create problems.

To understand how, think about how “real world” dating works. You meet a guy at a party, or a bar, or the bank, and here’s what you know about him: what he looks like.

How many times have you found yourself 30 minutes into an amazing conversation when a guy casually mentions his girlfriend? Or what about the guys you go out with four or five times before you realize your religious differences/educational backgrounds/grooming habits make you totally incompatible?

Attractive people can be intoxicating, and there’s nothing like making out with a guy you could’ve sworn had a bit role on The OC.

But in the moment, isn’t it just like kissing anyone else? And more of a self-esteem boost/story to tell your friends than a wildly passionate encounter?

Judging potential partners on looks alone has a time and place. But if that time and place is OKCupid, you’re kind of missing out on the advantages that belong exclusively to the cyber world of romance.

The whole point of these sites is that you know, before you even message back, that SustekStaffer27 is purportedly single (and if he’s taken, so sociopathic about hiding it that you wouldn’t fare any better if you met him at a happy hour), that he shares some of your outlooks on life (i.e., has aspirations beyond getting drunk, tan, and/or laid), and that his interests could be compatible with yours. You don’t have to go on three awkward dates before you realize that he only likes to play video games in his free time, and you get to see answers to questions you could never get away with asking early on (e.g., where he sees himself in 10 years, whether he wants to get married, how old he is).

That’s not to say that you can’t write some people off based on what they look like. There are some people you’ll just never be attracted to—maybe your first boyfriend had hazel eyes and traumatic headgear, and you always associate blue/green irises with the time your braces got stuck together.

If you find someone physically repulsing,  you might be fighting an uphill battle if you try to let his personality make up for it.

But if he looks great on paper and his picture only elicits a, “meh,” don’t be so quick to write him off completely.

It’s amazing how quickly you can become attracted to someone who didn’t knock you off your feet the first time you saw him. A funny, charming persona can be much more seductive than those mile-deep blue eyes. And on the flip side, anyone can get used to beauty, and the more time you spend with a physical trainer, the more ordinary he starts to look.

That’s not to say that you should spend your days pining over every profile you come across, or messaging guys you’re not immediately attracted to. But if a guy messages you, try to read his profile before checking out the pictures. And if the words line up, but the photos leave something to be desired, remind yourself what you’re looking for.

If you’re not looking for more than a few hookups, by all means, weight the photos. But if you’re looking for a successful relationship, consider giving guy who looks good on paper a chance.

Online Dating Deathmatch: OK Cupid vs. Match.com Vs. eHarmony

When you decide to take the plunge into online dating, you’ve already made a big and sometimes difficult decision. You have to get over that knee-jerk reaction most people have to the idea of meeting a soul mate online, but now you an even bigger conundrum: which site do you choose?

Today, we’re going to talk about the Big 3  sites in DC (OKCupid, Match, and eHarmony) and how you should go about exploring the world of cyber romance.

First, the basics: OKCupid is a free site that reminds a lot of people of Facebook. It feels targeted at a younger crowd, and the quizzes can be as addictive and time-consuming as Farmville.  The profile is more structured—users answer specific questions, like “What are 6 things you couldn’t live without?” and tries to get users to post more information than “Who are you? What do you do for a living? What are you looking for?” Users can “wink” (which no one seems to do) or message when they see a profile they like. There’s also an option to chat via instant messenger. 

Match is a paid subscription service, although you can do some things without paying. The profile isn’t as slick as OK Cupid and tends to be more open-ended. You get a lot of “About me” responses that are pretty vague and some variation on, “I enjoy long walks on the beach and am looking for someone to share my life with.” The communication is similar to OK Cupid—when you see someone you like, you initiate a conversation.

eHarmony is another paid site that’s definitely targeted at the older, more serious crowd. The profile is more structured with OKCupid-like “quirky” questions, but eHarmony distinguishes itself with its communication process. When you like someone, you don’t just message them—you can send an “Icebreaker” that says something cheesy like “I like your smile,” or you can send him a message. The difference is that eHarmony pushes users to use a guided communication process, which makes users send and answers questions like “What books have you read recently?” before you can send an open-ended, unstructured messages.  You do have the option of sending a say-anything message right off the bat, but the user has the option of rejecting it and pursing guided communication.

Before we get into the pros and cons of each site, we’d recommend that beginners sign up for all three and see which they like best. OKCupid is free, and Match usually has a free trial period. eHarmony lets you create a profile for free, but you can’t see pictures or message anyone unless you pay, although they do “open communication” weekends where you can message without a subscription. Match and eHarmony also usually have money-back guarantees, where you can cancel in the first two weeks and get your money fully refunded. If you sign up for a shorter period, or cancel within the trial period, you’ll probably get an offer to resubscribe at a much lower rate.

But here’s our take on the offerings in the DC area.

OKCupid seems to be the best bet for the recent grads, students, and “young professionals.” Because it’s free, it tends to attract people who just want to test the waters of online dating, and you’re probably going to get a wide range of atypical users (Match and eHarmony seemed to have a lot of overlap, but OKCupid seemed to have more users who weren’t singed up for the paid subscription sites). Basically, it seems like a younger crowd who would prefer to meet dates in “real life” (e.g., in bars) but got sick of trying to meet Mr. Right in AdMo.

OKCupid claims to have a scientific method for creating matches. There are basically just a bunch of questions on a wide range of topics (from religion to education to math problems) and you select your own answer to the questions, answers that would be acceptable for a partner to answer, and how important the topic is to you. They use this to match you up with people, sometimes to varying results, but you do get a chance to see, for example, how important religion is to FaulknerHottie222.

In our experience, Match is to OKCupid what MySpace is to Facebook. That comparison might not be totally fair, but you do see more users who seem to fit the stereotype of online dating (e.g., shirtless guys, creepy messages). The selection might be better for older users who might be turned off by the “personality quizzes” and other more juvenile features OK Cupid offers. The matching feels a little more arbitrary, probably because they’re matching you based on a public profile (on OKCupid, you can choose to keep your answers to the matching questions confidential). People might therefore be more likely to exaggerate answers and paint more flattering pictures of themselves. Because Match matches people based on an idealized description of who they are and what they’re looking for, some of your “100 percent” matches might be people you wouldn’t go out with on a dare.

We say this all the time, but paid subscriptions do not mean better results. If anything, paid users have made an investment, and they’re looking to get something out of it, which might mean more aggressive messages, a push to meet in person faster, etc. More “serious” users might be people who’ve had so much trouble with “traditional” dating that they’re willing to drop cash for something that works. That doesn’t mean that all subscription users are desperate, weird, or creepy—most probably aren’t—but there does seem to be this misconception that the paid sites attract more desirable users.

eHarmony was our least favorite site, mainly because the barriers to entry seem unnecessarily high (you have to spend about 2 hours filling out really long surveys before you can see your matches), and there are so many roadblocks to communication. It might seem like sending a message with something along the lines of “What’s your favorite book” would lead to more substantive conversations, but sometimes it pulls you into extended communication with someone who might have revealed his true colors if he sent you an initial message that said something like, “I like to take care of my body and hope you do too.”

The OKCupid-style questionnaire might lead to better matches, but it’s so hard to actually talk to anyone that we ended up giving up because we couldn’t take the frustration.

Again, it might be better for an older crowd (and that doesn’t mean super-mature 23-year-olds—it means people who are looking to date a 40-something), but it seemed pretty tedious when a 20-something can find (and communicate with) plenty of matches on the other two sites.

Let's Play Matchmaker

The biggest hurdle sites like match.com face is that people have an incentive to paint an overly favorable picture of themselves. You’ll get fewer responses if you mention you have a fear of commitment, but it’s harder to find other people who have trouble settling down when you can’t advertise that facet of your personality.

Because of this, we’d like to try a matchmaking experiment in the DC area. It works like this: you email in your responses to the ten questions below (to datethedistrict@gmail.com), and we’ll match you up with someone we think you’d like.

1.     Do you have any post-secondary degrees (i.e., anything higher than high school diploma)? If so, from where and in what subject(s)?

2.     Where do you see yourself in 10 years?

3.     If you didn’t have to work for a living, what would you spend your days doing?

4.     Describe your most recent relationship.

5.     What are you looking for in a partner?

6.     Why have your last three relationships failed?

7.     What are you most proud of?

8.     If you could change one thing about yourself, what would it be?

9.     What could you spend all day talking about?

10. What could you spend all day listening to?

11. Anything else you want us to know?

Entries will remain strictly anonymous, but if you’re super paranoid you can send in the first round of responses from a fake email address. If we think you’d make a good match, we’ll ask you for a picture. Neither the picture nor your answers will be shared with the person we match you up with. We’ll e-troduce you (awww) and leave it up to you guys to schedule the first date. After the first date, we’ll ask you to send us a write-up of how the date went (what worked and what didn’t) and whether or not you’d see the person again (and why). No write-ups will be published, but we may use some of your insights in an upcoming post, but any identifying details will be disguised beyond recognition (if you want proof, ask our friends, whose love lives we’ve been writing about for more than a year now).

The more brutally honest you are, the easier it’ll be to match you up (and remember—no one else is going to see your responses).

For the time being, we’re going to limit entries to the DC area (sorry Bmore).

Happy hunting!

Why Two Dates Aren't Always Better Than One

When two 20-somethings go on a first date, it’s probably safe to assume that one or both parties has other similar outings lined up for later in the week.

After all, the vast majority of first dates won’t work out, and you’d be crazy to cancel on that guy you met at kickball just because your friend’s cousin finally asked you out, and you’d be just as crazy to say no to the cousin just because you’ve been on two dates with the kickball guy, who, now that you think about it, is 27 and still interning on the hill.

There’s nothing morally reprehensible, or skanky, or even just icky about dating multiple people at the same time. There’s nothing wrong with giving a guy your number when you’ve been on a few great dates with a guy from OK Cupid.

If you put yourself out of commission any time a new guy comes up, you might give up a lot for a guy you could lose interest in after a few more dates.

It only becomes an issue after you hit that murky double-digit date mark where you don’t want to DTR, but you’re thinking this is headed toward exclusivity. You hope he’s not seeing anyone else, but you’re not sure, and the impulse to ask is getting harder and harder to ignore.

There are all kinds of ways to overcome this urge to launch into a “where-is-this-going” conversation, which, as we’ve discussed, is a bad idea.

But one of the worst solutions is filling up your free nights with more dates.

It’s not because it’s unfair to the guy or unladylike—it’s because it’s unhealthy for you.

When you’re seeing someone you like and filling your social calendar with guys who asked for your number, you’re using these dates as a way to protect yourself if it doesn’t work out with the guy you like.

Rejection stings each and every time it happens, but when you try to preemptively ease the pain by giving yourself more than enough backup options, what you’re really doing is curing rejection with validation from other people.

The problem with this remedy is that it makes you dependant on what other people think of you. You can’t be happy unless someone else likes you, which is a really inefficient way to find personal satisfaction/contentment. If you can’t feel good about yourself unless someone else is showering you with compliments, you’re going to waste so much time seeking out people who otherwise wouldn’t be worth it.

When your sense of self-worth relies on other people, you’re setting yourself up for unhappiness. People flake out for no reason and lose interest over things you can’t control. The more weight you put on their validation, the bigger the letdown.

When you deliberately line up other dates when things are going well with another guy, you’re also setting yourself up for bad dating habits.

That’s not to say that you shouldn’t go out with a friend of a friend that you’ve met a few times, who seems really great, and who you think might be a better match than your current prospect.

But when you’re handing out your number to anyone who asks and getting drinks with guys who set off warning bells before they even ask you out, you’re establishing a pattern of behavior that sets relationships up to fail. You’re learning to keep your distance, sneak around behind someone’s back,  and stay as far away from monogamy as possible.

We should say that most women don’t have this problem—if anything, some could use a lesson in not getting attached at the drop of a hat.

But for the rest of us, successful relationships usually don’t come from keeping as many options on the table as possible.

And if you stop relying on other people to tell you how great you are, rejection won’t sting as much in the first place.

Holiday Romance for Less

One of our astute readers sent in this money-saving tip for those of you who like the paid dating sites.

This reader’s match.com account had expired, and she was trying to unsubscribe to sing up for a different website. Unsubscribing was a multistep process, and when she got to the end, they offered her the option to resubscribe for 50% off.

So if your match (or any other account) is about to expire and you do want to keep your account, it’s cheaper to pretend that you don’t, go through the process of unsubscribing, and then resubscribing at the end when you get the 50% discount.

Or, if you want to try out a site for the first time, it might be worth it to sign up for one month, try to unsubscribe at the end, and use the 50% discount to snag the 6-month subscription for less.

Monday News Roundup: Background Checks and Online Dating

The New York Times ran an article yesterday on background checks for online dating sites.

While this article had a few good tips on safety (like always meeting first dates in public), but for the most part it felt like sensationalized nightly news, painting the world as a much more dangerous place than it actually is.

Yes, some people on these sites might have spouses, or criminal records, or dangerous intentions, but so do people that you meet at coffeeshops, bars, night classes, work, even house parties.

We seem to have this idea that rapists and criminals are drawn to the internet. It is, after all, easy to hide behind an assumed identity when you can post whatever picture you want, but it’s equally as easy to lie in person. Sure, you can’t fake your weight or age when you’re having a face-to-face conversation, but when was the last time you asked for ID when a guy gave you his name?

People you meet at bars have no incentive to disclose a criminal record, and just because someone said it to your face doesn’t mean it’s true.

The fact is, rape wasn’t invented by the internet, and you’re at just as much risk when you go around meeting people in “real” life too.

Unfortunately, this article provides no numbers, and it doesn’t seem like there’s been extensive research comparing criminals who target dating sites instead of deserted alleys, but we’d bet that the percentages are about the same, if not lower in favor of online dating. If there’s anything CSI’s taught us, it’s that a lot of criminals get their kicks from the challenges.

But the main issue with this article is that it fails to discuss the biggest potential hurdle for these companies that offer background checks on online users, which is that they rely on accurate information. If you want a background check on SurfBoy212, you’d need his full name and date of birth. But if someone’s trying to conceal a criminal history, he’s probably not going to offer up honest answers to your inquiries.

Even if they’re not trying to hide anything, how are you going to go about obtaining a DOB? It reminds us of the date-rape kit David Cross always carries:

That’s not to say that you should have to feel embarrassed/apologetic about looking out for your safety, but the main issue is that you’d probably have to be upfront about it to get the correct information. This probably isn’t going to create the most favorable impression for your date, which again, would be OK if the results would be accurate.

But because a guy with something to hide is probably going to lie in the first place, you’re risking a lot for a very unlikely payoff. The fact is, you never know when someone’s telling you the truth, and if meeting guys in real life gives you a false sense of security, that’s probably more dangerous than skeptically online dating.

Having "The Talk"

Sometimes, starting a new relationship can be more frustrating than perpetual singledom.

Obsession climbs to new heights, and so much feels open to interpretation. Is he seeing other people? Should you be? When is he going to start calling you his girlfriend? Should you ask?

We’ll address dtr (defining the relationship) first.

Simply put, it’s never something you should bring up. Nothing’s less sexy than starting a conversation with, “We need to talk…”

The problem with dtr is that it makes you look insecure and needy, like you can’t be happy or satisfied until you have a label. Who would you rather spend time with—a guy who’s cool and funny and laid back, or a guy who asks you to be his girlfriend on the first date?

And at the end of the day, a label means nothing. He could call you his girlfriend and spend his business trips macking on everything with a vagina, or he could insist that you go out to dinner with five of his friends before he’s started using titles.

The way he acts is much more important, and if he’s taking you out, calling to check in, and doing things that make you happy, it’s heading in the right direction.

And whenever one person tries to dtr, it automatically gives the other person the upper hand. The person looking for a title is going to seem more invested, more eager, and more interested in the other person. Why not give yourself the upper hand by waiting for him to initiate the proceedings?

OK, you say, but what if he’s seeing other people?

This is a very distinct possibility, especially at the beginning of a relationship. If he’s dating, it probably means he’s trying to meet as many women as possible, because most relationships don’t work out.

At a certain point, monogamy becomes the expectation, but that point is different for every person. You probably have crossovers you wouldn’t like to admit to in your past, but having a conversation isn’t the solution.

If he’s still seeing other people 6 months in, it’s probably not because you didn’t have “the talk”—it’s because he’s probably not that interested in monogamy in the first place. And a guy who’s still dating after half a year probably isn’t acting like your boyfriend or inviting you home to meet his parents.

That’s why it all goes back to actions. If he’s behaving in a manner that’s deserving of your affections, return his calls and accept his invitations. If he’s not, stop making plans with him.

And if you really want him to start calling you his girlfriend, the best thing you can do is act like he’s not your boyfriend. Introduce him to people as your “friend.” Don’t let your friends say, “I’ve heard so much about you.” Let him jump in and say, “Actually, I’m her boyfriend” or confront you about it later.

It might be that the dtr conversation hasn’t even crossed his mind. But when you do things like call him “my friend Derrick,” you’re forcing him to think about the issue.

You always find something when you’re not looking

When people are in the mood to dish out dating advice, many love to say, “You always find something when you’re not looking.”

The implication is that relationships only come along when you’re so frustrated that you stop looking, like the universe is taking pity on you or something. And the “advice,” if it can even be called that, is what—to stop looking for a relationship?

This relationship platitude is kind of like saying, “When you lose something, it’s always in the last place you look.” It sounds right until you think about it for .2 milliseconds, and then you realize this gives you nothing and you’d be better off burying a statue of Saint Francis upside-down in the backyard.

“You always find something when you’re not looking” also has some ring of truth to it—you’re more likely to find a relationship when you’re not spending 12 hours a day on match.com—but it’s not because you’ve stopped looking.

The people who seem most attractive to members of the opposite (or same) sex are those who seem happy, well-adjusted, confident, and, most important—busy. When someone seems like she has a full and exciting life, other people want to be part of it.

When you “stop looking” (which we would translate as “stop looking desperate”), you’re sending these kinds of signals. Your life seems so cool and interesting that you’re not going to drop everything to look for a boyfriend, and that’s precisely why guys are going to want to be yours.

So the trick isn’t to stop looking; it’s to make it seem as though you’re not looking. To project a persona that seems too awesome to settle for just anyone, and to market your life as something that everyone should want.

This means not skipping your yoga class for a date with a guy you met at Russia House. It means not showing up for singles mixers (do they even exist anymore?) and not begging your friends to set you up.

It means building a life that’s totally fulfilling without a better half. And when one comes along, it means making sure he knows he’s not the center of your universe.

Side note: we’re doing some transpacific traveling from now until the new year, so apologies in advance if we’re not posting as much as you’d like. We’ll be back to our regular schedule as soon as we recover from our NYE hangovers.

Survey the District: Online Dating Advice?

Today's question comes from one of our male readers (sorry if the picture was misleading for some of you).


Hey

Been searching for best way to meet new people for dating online. But is seems like there are so many losers out there and I just don' know where to start.

I've checked into dating sites like Match.com but they really don't seem to work that well.

What's your experience been. Any suggestion would be most appreciated.

Our regular readers know we’ve always been advocates of free dating sites.

The problem with Match, eHaromny, and other subscription sites is that, by requiring users to pay in, they attract people who are both so desperate to find someone that they’ll drop cash on the promise of potentially meeting someone they might like, and also more interested in cashing in their investment.

On the paid dating sites, everyone knows what you’re there for, and people are looking to make the most if it before their subscriptions expire.

This encourages unattractive behavior. People have an incentive to move fast, and, because they’ve paid money, they feel like they’re owed something.

On free dating sites, you’re more likely to get people who are just curious, testing the waters, and not overly committed to finding The One in cyberspace.

That doesn’t necessarily mean that users on the free sites will be more datable or desirable, but it does mean they’ll probably interact in a different manner. Their profile’s not going away if they forget to pay, so there’s no need to message you back immediately. They don’t need to arrange dates that week because they’re not even sure if this is the answer in the first place.

But it is important to realize that your zip code is probably the biggest factor in the success (or failure) in your foray into online dating.

If you live in a large metropolitan area, you’re going to find more potential matches than you will in a rural area. A bigger population means more options, whether you’re going to house parties or browsing the internet.

But why are you so quick to label other users as “losers?” In most cities, there’s actually a high percentage of “normal” people who have jobs, hobbies, lives, and, in some cases, dignity, that prevent them from attending singles mixers or hiring a matchmaker.

Diving into the online dating pool usually requires an open mind—after all, those of us who grew up with the internet were always taught to be on the lookout for pedophiles and other dangerous criminals lurking behind a mask of deception and online anonymity. 

You have to get past that, and realize that most of the people who sign up for these sites are probably more like you—looking to meet someone, but not interested in dropping everything for your search.

Online dating’s biggest selling point is convenience—it’s easier than getting set up and there’s a bigger selection than you’d find at a random bar (and meeting people in bars is a terrible idea to begin with).

Simply put, our advice is to sign up for a few free websites and see how it goes. Message a few women and go out on a few dates. If it’s not for you, it’s not the end of the world. But we bet you’ll find it’s way easier than calling that girl your mother’s been talking up for years.

Why We’re Just Not That Into He’s Just Not That Into You

We spend a lot of time throwing quick punches at the book all women were reading 5 years ago, He’s Just Not That Into You.

Today, we thought we’d finally explain why we don’t like this book, and why we think it does more harm than good.

Our problem isn’t with the message, which is, in its most condensed form, is basically this: if he’s not actively trying to make you his girlfriend, he doesn’t want to be your boyfriend.

That’s solid advice—too many of us spend hours obsessing about what a text means, trying to explain away the fact that he isn’t calling, texting, or telling you he wants to get serious. Sometimes we are wasting our time and energy on people who, for whatever reason, are never going to change their minds.

The problem is that this is where the message stops. He’s not into you, so get over it and move on to someone who is. And, most importantly, it’s not you—it’s him.

This isn’t always true. Sometimes it is you. Sometimes you’re clingy, or text too often, or talk about your ex, or tell him you’re on a diet, or engage in a variety of other behaviors that don’t reflect the awesome, amazing, self-confident person that you are.

HJNTIY would say, “Fuck him—wait for a guy who loves your neuroses!”

That’s certainly one solution, but a better one might be to behave in a manner that’s attractive to men. To make yourself less available. To project a friendly, confident, and independent personality. To make a guy work for your affection.

There’s definitely a point where you need to forget him and move on. But HJNTIY focuses exclusively on this point—not the before and after, which are usually the more important parts. The before is your chance to seduce, and the after is usually easier said than done. If getting over a crush were as easy as saying, “Oh well, he’s just not that into me!”, Facebook wouldn’t have expanded beyond Harvard.

It’s easy to obsess and hard to break the habit. It’s easy (once you know what you’re looking for) to figure out when a guy isn’t interested. But it’s much harder to avoid having to give yourself the HJNTIY pep talk in the first place.

Holiday Dating

One of our friends is going on a holiday dating hiatus. She’s locked her OK Cupid account until New Year’s and she’s postponing dates until after the ball drops.

When she first mentioned this to us, we were skeptical. It seemed arbitrary, and arbitrary rules are never the best way to make the most of a dating scene.

But then she explained her rationale. Holidays come with certain expectations for couples: awkward office parties, gift exchanges, dinner with his family. It’s tricky enough when you’ve been dating for a while, but when you’re still in the getting to know you stages, it can put a lot of pressure on both people (and the relationship).

Should he invite you to the holiday party? And if he does, how will he introduce you to his boss? Does he need to buy you a present? Are you going to buy him one? If he brings you home, will his mom get off his case? Will it freak you out if he asks?

If you meet a great guy at your friend’s ugly Christmas sweat party, we’re not saying you should tell him to call you after New Year’s.

But, if you’re like most people, this is probably the busiest time of your year. So if he calls you for a second date and you have to finish shopping, don’t be afraid to say so.

Don’t feel like you need to squeeze in too many first dates with a new person. If you space out your dates, there won’t be any ambiguity. He won’t show up with a gift, and you won’t obsess over what you need to get him.   

Making a Guy Jealous (Part III)

We spent the last two days talking about bringing up other guys in the presence of a potential partner, and we’d be remiss if we didn’t talk about the other side of the issue: what to do if a guy brings up his ex/other girls in front of you.

It’s a little more cut and dry, but if you’re seeing a guy, and he brings up a girl, it’s generally pretty bad news.

Let’s say, for example, that the guy you’re dating casually mentions going to a club with his friends last weekend and the hot girls who are “all over him.”

This is totally disrespectful, and while you might think you’ll look cool and nonchalant if you don’t make a big deal of it, you’ll also look like you don’t have a lot of self-respect.

He might not be testing you, but your response does reveal how much he can get away with. Don’t laugh or play along or point out his total lack of manners—change the subject as quickly as you can, but, more importantly, unless he goes out of his way to make up for this gaffe, you should probably write this guy off.

When you first start seeing someone, it’s unrealistic to expect him to stop looking immediately. But when he goes out of his way to bring up his extra-curricular activities, he’s basically bragging about being an asshole, and if he’s doing that on the first or second date, you don’t wanna see what he’s like 6 months from now.

Ex-girlfriends are a different story. Yes, it’s tacky and bad manners to bring them up, especially in front of a new girl, but the intent is usually far from malicious in situations like this.

If a guy spent three years with a girl, he’s probably going to have a lot of anecdotes that start with, “My ex…”

And while you might be too savvy to make this mistake, he might honestly not realize there’s anything wrong with talking about a person who was a huge part of his life for a time.

If he’s bringing her up every five minutes or giving you the impression that he’s still totally in love with her, that’s one thing, but if he’s just mentioning her off-hand, you just need to take control of the conversation and remove her completely.

If he says, “Yeah, my ex turned me on to 30 Rock,” get off the topic of Liz Lemon immediately—say something like, “Yeah, did you hear about her lifetime achievement award thing at the Kennedy Center?”

Don’t let him get into a conversation about her—you don’t have to be rude or abrupt about it, and don’t say anything like, “Let’s not talk about your ex,” just ask him a question that takes the conversation in a totally different direction.