Ask A Dude: Why Does He Keep Chasing Me?

Dear Dude,
I’ve known this guy for a about a year and a half who is a total player. I’ve seen him flirt with other girls and chat up anyone that glances at him so I never really thought anything of it when he hit on me– the run of the mill thing he always does and I was the victim of the night. I initially rejected him when we first met and since then, every time I see him its another offer to hook up in a different way. Through the many different times he has asked me I have considered it but am not quite sure I could deal with the backlash of it. All of my friends tell me not to hook up with him because he just wants to hook up with me to get another girl under his belt, but if this were true why still ask me?
My question for you is if all he does is talk to me and my girlfriends about how much play he has and how much ass he can get all the time, why is he still chasing mine? I moved across the country for part of the time I have known him and he still hit me up for half the time I was gone, gave up for a couple months, and then came back strong, trying again. While I’m flattered by it, I am unsure as to why he is doing it. Is it just the chase because I am possibly the first girl that has rejected him so many times? Is there more behind the asking? I am interested in him, but am scared of the reason why he wants to hook up so badly. Is it possible he wants to reject me when I finally say yes? I have no idea how to go about this…HELP!
The Chased.
Dear The Chased,
Sometimes I hate the players and the game. There’s the childhood adage that “he who talks the most, gets the least” (and yes, we’re talking about poon, here). On the other hand, some guys are just really braggadocios (which sorta sounds like douchey, doesn’t it?) and like to rub it in your face. Although, usually guys tend not to rub it in the face of girls they’re chasing but then again that can be their pick-up habits even though that seems counterintuitive because what if-BRAIN FREEZE!
Alright, I’m just chasing my own tail right now. Which is what’s so tempting to do in a situation like this where you’re navigating the mixed signal highway.
I’m going to both burst and preserve your TARDIS. Yes, men will keep trying to find a way to f*ck you even after months of rejection goes by. Sometimes actively, sometimes just when the opportunity to speak with you comes up. It seems illogical (and probably is) because, why keep trying when he could go get his fix from someone else? The answer is that the two ideas aren’t mutually exclusive. He can get a hook up from another girl AND still try to pursue you when he talks to you. It’s just…some guys are like that.
On the flip side, it’s entirely possible that the reason he keeps banging his head against the proverbial wall is that he’s got ulterior motives, like, he actually likes you as more than a night in the Plaza with strawberries and I Love Lucy reruns (does he look at all like Richard Gere ala Pretty Woman?).
My gut tells me it’s option A but then again I could be being cynical because, well, life and neuroses has shaped me so.
Here’s my question to you: What would happen if you said “yes”? Because you’re interested, you’ve owned that. Seeing where that interest leads you is the only way you’re going to find out one way or another.
You don’t have to have sex with him just because you agree to hang out with him, too. That expectation doesn’t even have to enter the equation. You can just say yes to spending time together. If he turns that down, then you’ve DEFINITELY got your answer. If he doesn’t, inch out a little further.
Insanity is doing the same thing over again and expecting a different result. So, do something different. Say yes. To not having sex. Then we’ll know if this dog’s all bark or bite.
Stay classy,
The Dude

Candy Dish: Hump Day
Candy Dish: Hump Day
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