Real Live College Guy Joe: If at First You Don't Succeed (In Making Dinner Plans), Try Again

Ever wonder what guys think, how to deal with them, or whether instead of listening to you, they just imagine you naked? Our Real Live College Guy Joe will answer all your questions about men and relationships with wit, clarity, grace and physical attractiveness (can you tell he wrote this intro himself?) all while imagining you fully clothed! Well, usually – he is a college guy.
This year in one of my psychology classes, I sat next to this guy, we’ll call him Ed.  And yes, I sat next to him because he was really cute. Toward the end of the year, we started talking and texting a little and even studied together a bit but never really hung out in a purely social setting. When we texted, we would always talk about hanging out but never actually do it. When school ended, we went back home for a while (he’ll be back at the beginning of August), and we have continued to text, usually about what we’re doing and talking about things we should do when he gets back. My past experience tells me that us talking about all this stuff doesn’t for a second mean that it’s actually going to happen, but I want it to! I feel like by now the precedent has been set that we’re going to talk about hanging out because we know it will never happen, and I really want to break that pattern. Should I just be really assertive? I don’t want to scare him off or make him feel like I’m coming on too strong because I do really like him. Help!
    -Baffled in Boulder

A guy would never waste the valuable time he could be spending mastur – I mean watching TV – by texting you about hanging out if he didn’t actually want to hang out with you. Who knows, maybe this past year he had something going on that prevented him from spending time with you: a family crisis, maybe, or he could be an international spy and didn’t want you to be seen with him because that would’ve put you in danger. 

And now, like you, he feels stuck in the little pattern you’ve established for yourselves and is scared to break free and ask you to walk dogs in the park. Maybe that’s outdated.  Maybe invite you to drink a malt and see the new feature at the drive-in. I understand you may be feeling led on because of his past behavior, but I don’t think he’s making empty promises – unless this guy gets some sadistic thrill from making plans and then bailing on them (Oh man, I see a blockbuster suspense thriller in the works! The Man Who DIDN’T Come to Dinner). But I’d put my money on the good old couldn’t-hang-out-for-various-reasons-and-now-feels-stuck-in-a-fruitless-pattern scenario. 
It’s like this: Say there’s a guy, we’ll call him Fabio (Since you named your heartthrob the extremely boring Ed, I guess by your rules we have to name the couch potatoes like super models). Anyway, Fabs watches TV all day. And every day during the second commercial break of Days of our Lives, a commercial for Al’s Turkeys plays. And, every day, Fab-ulous gets really hungry for a turkey sandwich. Al’s is only a five-minute drive away, but Fabio is so wed to his daily pattern that he can’t fathom getting up and getting himself his very own sliced bird on toasted sourdough. He’d buy one in an instant if he ever found himself in the store. But as it is, the commercial ends with Al’s signature, “Get your clucks for half the bucks!” slogan, the show comes back on, Alice starts b*tching about how Tom never did his part when they were raising the kids, and that turkey sandwich dims to a soft amber memory that Fabrillio will recall at times with a sigh.
Got it? For clarification, in this scenario, Ed is Fabio, and you’re a big turkey sandwich.