There are two types of guys in this world: the ones who want you to be their girlfriend and the ones who don't but naively think that's what they're supposed to do. The first type is the one who has taken you on actual dates. You've met his friends. He genuinely likes you. He wants to lock that shit down. So he's going to want to ask you to be his girlfriend—unless he can somehow convince you to ask him first.
There is something incredibly straight-forward and refreshing for a guy about not having to broach this topic himself. I remember a woman I was dating years ago casually turning to me while we were out with friends and saying, "I don't want you to hook up with other girls." That was fine by me. She agreed to the same. And then we were a couple for many years. For a guy, it doesn't get more amazing than that. No awkward conversation, no wondering if the woman is already seeing other people, nothing. Easy as pie.
Perhaps you aren't interested in making the first relationship move, though. Maybe you're afraid of freaking him out if he's not "there" yet. (A valid concern.) My analysis? If you've been casual for a while and the interactions are more than just hooking up after 1 a.m., my bet is that he's already thinking it and just hasn't gotten up the nerve to ask you yet. It takes time for a guy to work up the bravery to sit down at the end of a night of bar-hopping and just blurt out "I don't want to see other people. Okay?"
I know, I know, it seems frustratingly easy to utter a few simple words. But here's what's going through our heads: You might respond with "Oh already?", and we're going to be deflated. You might respond by saying you're seeing other people and need to figure that out first, and we're going to be deflated. You might say you have to think about it, and (you guessed it) we're going to be
This is one of The Three Big Maybe-I-Am-Embarrassingly-Misreading-This-Situation Moments for a guy.
deflated. Any answer other than an enthusiastic "Sounds great" is ego-crushing. This, the "I love you," and the actual marriage proposal are The Three Big Uncomfortable Maybe-I-Am-Completely-and-Embarrassingly-Misreading-This-Situation Moments for a guy. So no matter how you feel about coupling up, please, be gentle.
Oh, and then there are the guys who are asking you to be their girlfriend because they think you want to be their girlfriend. In their heart of hearts, they aren't interested in pursuing you long-term, but also don't want you hooking up with a lot of other guys.
Take my friend Jake, for example. Jake was hooking up with a woman casually for about a month. He wanted to see her so he called and asked if he could drop bythat night, maybe bring a bottle of wine. "Sounds fun," she said, "but I have a date."
Jake did what many men do when they feel threatened: He tried to block out any competition. The next time he saw her he asked her, seemingly casually (inwardly freaked out) if she really liked this guy. She liked Jake better. Now, Jake didn't foresee a long-term relationship with this woman but wasn't ready to cut her loose either. So what did he do? You know the answer. Naive, dumb Jake. Flash forward a month and his attention was drifting to other women, she was always angry about what a bad (read: non-existent) boyfriend he was, and they broke off their faux-mance.
The good news? Most men fall into the first camp. We genuinely want to define the relationship and move it forward. We just really appreciate not having to bring it up ourselves.
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