I love your article and mostly pick up Flagpole to flip right to this part!  First time questioner, though. I have been single for several years now with a couple of dates here and there. I have been moving around so much, it wasn't practical to put much energy into meeting people. But now I'm going to be in one place for a while, so I'm putting myself back out there. I'm 30, have been married before, and am driven and independent, so finding someone whom I'm interested in, and is at my level, is a challenge.  

I had a class with a guy last semester and immediately had a crush on him, but left it at just that until recently. I see him regularly from another activity we have in common. Ah ha!... my moment to truly get to know this person. I've spent the past two months casually talking and here and there doing activities; he's always willing to help and offers to do so with various projects I have on my plate and is truly nice.  We have a lot in common and broach topics of religion and life... He even started giving me hugs when I would leave (minus the last time I left when I got a high-five...?). 

I just want to know if I should stop crushing and put him in the friend zone or keep on gently pursuing him. My one clue is that even though he invited me to a full-day event recently (which we had a good time at, full of conversation and laughter), I've been doing most of the inviting (Hey, I'm cooking dinner, wanna come over? Hey, I was going to go mountain biking, would you like to go?). This sort of thing. My first reaction is that... if you want something you go after it... i.e., if he wanted to hang out with me then he would invite me.  I have other distractions and talk to other guys (to not place all my eggs in one basket), but I keep thinking about him.  Friend zone him to get over the crush or keep the spark alive because he might actually like me, too?
Thanks!
Sparky Friend

First of all, I wouldn’t read too much into the high-five. I have been known to do that after sex, so I don’t consider it less personable than a hug, as long as you have had previous hugs. His invitation to the all-day event is a great sign. My question is does he accept your invitations to dinner and biking? Has he ever? When he doesn’t, is there usually a reason? And did the invite to the all-day event come after he maybe declined some of your invites? If he has always said no to your invitations, then that is a bad sign. But then why would he invite you to something? Seems like even if he said no a bunch of times, maybe he extended an invitation of his own so you wouldn’t give up. Is he a pretty busy guy? I think you would be remiss to put him in the friend zone after a successful outing.

I also think you should probably get a wee bit more assertive soon, though, so the dreaded “Friend Zone” doesn’t happen by pure inertia. If you aren’t sure what’s going on or where you stand, and you’re too shy to just kiss him, maybe you could lay your proverbial bicycles on the dining furniture? I don’t know. The kiss would certainly be easier, but if it misfires it might make things weirder. I just can’t believe you have no idea what he’s thinking. I think you should go for it.

I have returned after a long absence and have discovered that the social landscape I once cultivated has become a barren wasteland. I just don't know what people want, really, and whenever I try and engage in friendly correspondence with anyone, most don't return any messages, except for the most cursory responses. I suppose I am and was never a very big part of any of these people's lives... but I am/was under the delusion that there was once a time where we were friends and always did our best to maintain that friendship. Now, I am either faced by disinterested silence or competitive animosity. I just feel like people are so suspicious these days. Am I clinically insane? Or just a socially inaccessible fool? Should I continue tilling fields, even if they don't sprout, in defiance of gods and men? Perhaps I'm just an unreliable narrator of my own life.

A friend told me recently that I was a catch and I retorted…"More like an old trout."

Late-20s Fitzwilliam Lament (set to the tune of "V-8 Ford Blues")

P.S. Maybe I should stop being a negative jackass... but I'm never one in public.

Disinterested silence I guess I understand, but competitive animosity? What exactly are you competing for? I doubt you are clinically insane, but you may be socially inaccessible, and you are definitely an unreliable narrator—though I would argue that it makes you an entertaining read. I would love to help you out, LTFL, but I need more information. Are you texting people that you haven’t seen in a long time and expecting a meaningful exchange? Are you sending them Facebook messages? Are you just sending random blurbs? Is it possible that they just don’t have time to respond and that an invitation to hang out might be in order? Or are you telling me that they are actually physically avoiding you? You have been gone for a long time and their lives have changed. What you need to do is see what they are doing and how you fit in. If you don’t, then I guess it’s time to find a new group of friends. Happy to engage further with more details, but that’s all I’ve got for now.