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.

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.