Advicereality check

Reality Check

I am a young, intelligent, outdoorsy guy living in a rural place in a rural state. As I’m sure you hear a lot, it’s not easy to meet people here, but it’s only harder because I’m gay. It’s not like the local bars even have a singles night, so you can bet there’s no watering holes for those of us of the fabulous persuasion. Because of that, I have turned to technology, and here’s where I need your help. My most recent foray into the digital ether involved Grindr, a dating site that puts a preference on geography. Sure, the most basic function of Grindr tends to be of a physical nature—and I’m not opposed to such encounters. But given the sheer lack of numbers playing for my team in these parts, most guys are playing it too cool for school. It takes a lot for me to start a conversation with someone, but recently I did. I finally met a guy of a reasonable distance, and with whom I had some kind of banter. Conversation went as usual. Hey, what’s up? Crazy weather, aye? What you looking for? Real stimulating conversation. Anyway, he requested I send additional pictures, and I sought to oblige by browsing through my camera roll. Two clicks later, and my phone is seized in a cycle of data being sent. Try as I might, I couldn’t stop the entirety of my camera roll being sent to that evening’s gentleman caller. These pictures consisted mainly of pictures of foods on which I had put poached eggs (I love breakfast; get over it). There may also have been a close-up of a toenail used as a diagnostic tool by my out-of-state doctor. Immediately, I’m aware that my battleship is sunk. Yet, he responds with “hot.†And then nothing. Radio silence. I am mortified. Now where do I go? I’ve made a complete ass of myself, and still his aims are guided by his heat-seeking missile. I’m lost. I’m not sure what my question is, but I need some kind of guidance here.

Camera Shy

Well, the fact that he responded at all is interesting. And the fact that his response was kind of hilarious is a good sign. On the other hand, the fact that you haven’t heard anything since then is not great. But you made the mistake, so in my opinion the ball is in your court. You have to decide to either completely walk away from this, or you have to follow up. You could say something like “Well, now that you know my entire life story in 27 breakfasts, do you want to meet in person?†Or how about “I may not have mentioned on my profile that I am a technological genius, but now that I have accidentally sent you my entire camera roll, I guess you’ve probably sussed that out.†Make a joke out of it. That’s all you can do. Express your mortification, but roll with it. If he responds in a stupid way, or doesn’t respond, you probably wouldn’t have hit it off with him anyway. Good luck.

I recently got contacted via Facebook by a guy that I haven’t seen since high school. He dated my sister for a short time before she went to college, and then he and I had an incident a few months later. I was 16-years old, had had way too much to drink, and was trying to get him to give me a ride home because he was leaving a party and I couldn’t find my friends. My recollection of the situation is that he was being a big jerk and he was trying to tell me that he wouldn’t give me a ride unless I had “something for him†in return. I was angry and disgusted and I ended up walking home. I never spoke to him again. He lived a few towns over, and we did not travel in the same circles normally, so I never saw him and had totally forgotten about it. This was 25 years ago. So you can imagine my surprise when he contacted me with a very effusive note about how he remembers me and that he dated my sister (she is not on Facebook and has long since left our small town) and how am I? I wrote back that I did remember him and that I was surprised that he would contact me considering what had happened the last time we saw each other. He didn’t remember, but I told him what I remembered. He gave me his recollection (which was fuzzy and did not involve him being crappy to me) and seemed shocked and upset about my memory of it. He didn’t say I was wrong, mind you, but he did say that he didn’t remember it that way. He was 18 at the time, and now that I am a divorced woman in my 40s with a teenaged son, I obviously am thinking about it in a more forgiving light. We have exchanged some e-mails. He still has letters that my sister sent him. The whole thing is kinda weird, but I would be lying if I said I wasn’t a little bit intrigued. He looks great; he seems like a nice guy with his shit together, and I haven’t met a whole lot of those in the past 10 years since my divorce. My sister has nothing but nice things to say about him, but she is married and lives in another state, so it isn’t like she is a possibility for him. So now he wants to go out with me. What do you think, Jyl? Should I give him a chance, or is his behavior then a warning to me about who he is?

Not Kids Anymore

Give him a shot. You were 16 and drunk the last time you encountered him, so it is possible that your recollections are a bit… cloudy. Your sister, who actually dated the guy, has nothing but nice things to say, and since she isn’t interested in him now, she has no reason to lie about it or paint a rosy glow on it for no reason. What I would be most wary of is the fact that he may still be very attached to your sister, since he still has letters from her lying around after all these years. Proceed with caution, but do proceed.