Survey the District: Should I Bother Trying to Tame an Asshole?

Dear Date the District,

Currently, I am in a situation that has the potential to turn into naked-makeout disaster zone or perhaps something more substantial and I would love your advice on it. I have had a crush on this guy from my town since the 1st grade. There is something about him that has always worked for me, and still does 16 years later. While this crush never developed into anything during my formative years, I've recently gotten back in touch with people from high school since graduating college and moving back home. Said crush and I never hung out socially outside of school, and over the course of the last 2 months have seen each other maybe 5 times or so. Every time involves a group of friends either at a bar or someone's house, and alcohol. He has flirted with me a great deal while out with friends every time I go out with him, and insinuated make out sessions that I held out on (up until last weekend that is). Mutual friends of ours have told me that he has never been in a real relationship before, and think that I am "too nice" for him. (Meaning, they don't want to see me attempt to pursue this route with him because I will end up getting my heart broken like the wounded soldiers before me.) We hooked up last weekend, post-bar (not drunk, but not sober) and he attempted sex but I steered him in the direction of a blowjob instead (which was truly difficult because we had intense chemistry and were having a great time together and *sigh* I have been wanting him since the tender age of 6). My question for you is: should I bother putting in the effort with this guy if he's never had a girlfriend? Is there even a likelihood of me potentially being the girl that breaks the mold? (i.e. will your method of projection work on this guy?) And if not, should I abstain from hooking up with him again? It's been awhile since the last time I hooked up with anyone and the dry spell is KILLING me, but I don't want to pretend I'm one of those girls who "doesn't want a boyfriend" and is cool with "being casual" because I get jealous and know that won't work for me. I'm totally lost. Side note: he is a weak thumbed texter.

It’s a tempting trap: if you don’t think it’s going anywhere, why bother playing games? After all, holding out is hard, and it’s easier to just text him first.

Here’s the issue: playing games isn’t guaranteed to work. But not playing games is almost 100 percent guaranteed not to get you what you want.

We see this time and time again. Girls decide that it’s not worth playing games because he’s not datable, or he’s not cute enough, or he’s too much of an asshole to bother. They think the fact that they’ve resigned themselves to not even bother trying will protect them from getting hurt, but a few weeks later, when he’s in major blowoff mode, the sting is even worse—partially because it’s unexpected.

You never know how things are going to progress. This guy could be totally untamable. Or it could be that no girl’s ever made him work for it before.

But if you text him first and give him the naked makeout, you’re never gonna find out. And, chances are, he will start blowing you off. And what for?

We understand the excruciating frustration of a dry spell. But is it really worth the pain you’re going to feel when you go three weeks without hearing from him?

Our advice would be to keep making out with him in public. But don’t take things back to his place. If he texts you at 3 a.m., ignore him (and FYI, that means no texting him back in the morning to say, “Sorry, I was sleeping”).

Girls rarely (if ever) get anything out of playing it straight. If you’re sexually frustrated, invest in a vibrator—they never forget to call.

There’s something to be said for human contact and the validation that comes from proof that your crush desires you sexually.

But won’t it feel worse to know that he did want you at some point and, for whatever reason, isn’t responding to you now?

The more you like someone to begin with, the easier it is to get obsessed when he doesn’t call. If you let him have it that easily, you’re probably going to regret it.

You say you two have a lot of sexual chemistry. Which totally makes sense—if you’ve been waiting for someone for 16 years, the payoff’s going to be even bigger.

But think about the sexiest parts of hooking up. It’s not the blowjob, or the naked dry-humping, or even actual penetration. It’s the sensual kisses, the tentative touches, his lips on your neck, etc. All of this can be accomplished in a dark corner of a bar.

With the public makeout, you can cash in on the electrifying sexual chemistry without sacrificing your dignity.

And if he wants to take it further, he can ask you on a date.