For the past five years, Steven has been shoveling advice at singleape.com. The following is a weekly selection for the readers of The Huffington Post. Feel free to give opinion or send in your own questions.
So at the very end of November I run into this guy I had a crush on years ago (still do) and find out we are in school for the same master's (different schools) and that we seem to have a lot to talk about/in common, more so than we did back then when he didn't like me as more than a friend.
The thing is, we've been hanging regularly ever since I ran into him and it even involved getting physical last week, but he says he's been depressed (not on meds, fyi) since he can't find a job right now and has family, stress, etc., so I'm wondering if it's going to go anywhere further, but I don't want to ask because I figure it'll just stress him out... He calls himself a loner and says he is neurotic/has anxiety so maybe I'm just a shoulder to cry on for him but I like him as more than a friend and I know I show it.
I feel like I get mixed signals but I just attribute it to his emotional problems... He says he is an insomniac and stressed out, etc., but when we hang I feel he's relaxed and comfortable and not as bad as he claims himself to be... Anyways, I'm rambling and so far my plan is to just be patient and not push anything (even though I feel maybe I'm being pushy) and see where this might go, but I feel like it's dating (very casually) blah.
Is that even a question? This is why people write to me, because they've exhausted their friends' patience with the minutiae of their situations. The good news is I can ask the questions most friends wouldn't dare ask, like, why do you even want to date this guy? He sounds more like a '72 Volkswagen bus with a cracked engine block than anything that resembles boyfriend material. A stressed-out, jobless, insomniac with anxiety and neurosis who is too pussy to make a decisive call on a non-girlfriend. Call me wack-a-doo but are there no other possibilities out there? Some masters stud with a Jake Ryan disposition and a Jon Stewart brain? Am I romanticizing grad school too much?
Now that you know where I stand, I'll entertain your inquiries as if I did truly believe you and this guy were a match made in grad school heaven. To do so I need to re-establish one stereotyping truth: when it comes to dating we are all total idiots. Girls are dumb for many reasons, mostly involving this play-with-your-food approach to poking and pawing the prospect until it (he) jumps in your mouth (figuratively). For guys, their idiocy is more life damaging. To simplify a situation such as your own, most guys see their heap of personal problems and wrongfully deduce that a girl would just be another shit-storm on the pile. What we (he) almost always fail to see is that a good woman is actually the answer to all our (his) problems. I'm not being a pony-tailed kiss-ass S.N.A.G.* here, I'm just telling the truth. Deep down 'your dude' knows this, which is the basis for the magnetism to your companionship.
If you really want to get under the hood of this project-dude, you're going have to show off your worth a bit. Be the leaning post he so desperately needs, but do so with a calculated discretion that doesn't mutually exclude his need for establishing something further. In the words I told a friend just yesterday, "Why buy the girlfriend when you can get the comfort for free?" Show off the wares, but ease up on the free samples. From my boy perspective, I'd say that pretty much only means that you don't give the impression you've taken yourself off the market. Go on dates, have other crushes, and live life as if you don't have a boyfriend, because you don't. I know this is the curse of the female; the steely resolve of an astute hunter when your sights are set, but do your skill set a favor and fake some tepid interest. To continue with the hunting analogy, you're firing too early and need to lure him a lot closer.
I'd say I hate to teach you how to play games, but the truth is I love it. Our collective human curse is that we are all so damn predictable. It's a fate that's as impossible to escape as the need to pee, so we might as well exploit it in our favor every once in a while. If ever there was a dude who sounds desperately in need of some good ol' womanly comfort, it's this '72 bus you're trying to date. All it'll take is showing him what he could have while simultaneously displaying in no uncertain terms that he doesn't have it yet. Game on.
*Sensitive New-Age Guy not Society of North American Goldsmiths, that makes no sense!
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