The funny thing about "hitting on" a woman (opens in new tab) is that, while we guys are often the aggressor, we usually fake: confidence, looking like we are in control, and "smoothness." Internally, there's a storm of thoughts in my head that are not only comical, but should be enough to boost your confidence (opens in new tab) any time a guy hits on you.
Knowing what we are thinking might put you at ease. Here are the thoughts running through my head as I approach and hit on a girl:
Do I Look OK?
As I'm approaching a girl (opens in new tab), I'm wondering if my hair is flopping strangely (even though I'm constantly fixing it) (opens in new tab), if I have any "crust" on my nose or mouth (opens in new tab), or if my fly is down. I run through this checklist in slow motion as I'm walking toward her. Even while I'm talking to her, I'll mentally run through all the things that could be wrong with my appearance. I'll fail quickly if I'm not looking good. (opens in new tab)
How Many Other Guys Have Tried?
I hope she's not thinking "here we go again," and adding me to the pot of lame guys (opens in new tab) that she's already turned down. Most guys try to set themselves apart from the pack. Chances are, if I'm the third or fourth guy, the other guys have given "males" a bad name, and this girl will want nothing to do with me (opens in new tab).
Why Did I Say That Stupid Thing?
I scrutinize things I say to a girl as they are popping up my mind and as they are coming out of my mouth. (opens in new tab) It's amazing that I can say so many stupid things with that diligent filter. OK, the filter is not diligent at all. But I even question the not-obviously-stupid things I say after I've said them. In fact, a large percentage of the things I say are dumb, especially when I venture into "off the beaten path" topics in an attempt to separate myself from the pack. (opens in new tab)
What Should I Say Next?
Asking questions is supposed to be good, but I'm too busy internally deciding what to ask or say next (opens in new tab) while a woman is answering or talking to me. So, she's white noise while I'm frantically searching my mind for the next words.
Am I Overstaying My Welcome?
Sometimes it's best to leave on top and walk away with a positive vibe. But, I have to figure out if I want to get a number or leave and come back. Bottom line: the girl I'm hitting on didn't come out to spend time with me all night. Even if it's going well it might be best to walk away and let her think about it a bit instead of hijacking her evening.
Is She Flirting?
Flirting is overrated for a few reasons: a. Many guys don't put much stock into it because flirting isn't always serious (opens in new tab), and b. Clueless guys like me can't even tell when a girl is flirting. I definitely notice the obvious moves: laughing at my dumb jokes, touches, eye contact (opens in new tab), but I'm never really sure if she's just flirtatious in nature or if she really intends to flirt with me.
Why Can't I Be Myself?
When I meet a girl for the first time, I'm extra courteous and behaved (opens in new tab) (provided I'm not drunk and acting like an idiot). It all feels so fake sometimes. I want to admit you're really hot, I want to admit that I have nerdy vices in my life (opens in new tab), I want to talk about crazy history and music. I have to be a "restrained" version of myself (opens in new tab) the first time around, but it's not fun holding back my personality. And then, of course, I wonder if she's holding back her personality too.
Is There an Angry Boyfriend Around Here?
It's all fun and games until an angry boyfriend pulverizes me. It's so awkward when a boyfriend catches me in the act of hitting on his girlfriend. What's more, I might just be a pawn in her game (opens in new tab) to make her boyfriend jealous (opens in new tab). Do us all a favor and somehow clue us in that you're single early on — or get rid of us by mentioning a boyfriend (you can pretend you have a boyfriend to get rid of us too) (opens in new tab).
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