Dear Dr NerdLove,

In high school, I was basically asexual aromantic (or that’s how I’d have probably identified if those terms were more commonly known then). I didn’t care much about how undressed, looked or ate. I’ve been a chubby guy for basically my whole life, and since I never really cared about romantic or sexual interest, I didn’t really notice or think about my weight beyond health reasons. Despite being 240 pounds and a huge nerd with Asperger’s, I was apparently considered attractive in high school. Four girls asked me out between middle and high school (who I would always say no to since, with a my less keen knack for social skills at the time, I thought it’d be rude NOT to say no if I wasn’t interested) and I even got a “best eyes” accolade in my yearbook to my surprise. So I had always figured that if I had ever tried to start dating I wouldn’t have too much of a problem.

By the time I actually became interested in girls, however, things had changed. I had gained 50+ pounds during college (between stress eating and not really paying attention to my diet), now up in the 290+ range, and despite having improved myself in other ways (hygiene, not just wearing polo shirts with basketball shorts, not blurting out or rambling on about any interest I had at the time constantly/being a bit more reserved), I didn’t have any luck. I managed a few first dates but either they were uninterested or went for someone else completely or eventually went for people like me (nerdy types) but skinnier. Earlier this year I even reconnected with a friend I had been told had a crush on me in high school. She still seemed interested when we first got in touch on Facebook  and there seemed to be a vibe that she was interested. When we met up at a party though, it seemed as though the indications that she was interested in me had faded. While I’m fine with just being friends, I can’t help but feel bad that I may have missed the boat on something good because of my weight.

So this year, now that I had income to spare it, I started investing in getting a girlfriend. Personal trainer, diet shakes, getting on every dating app that seemed decent enough. While my health has improved and my muscles are stronger, my endurance and stamina had greatly improved, I still struggle with actually losing the fat, so my attractiveness physically is about the same. Eventually I did manage a hookup with a girl for a night that was pretty okay, but I wasn’t super attracted to her and I mainly did it so I could actually lose my virginity before 25, and to make all this sunk cost actually end up in something.

Now with some of my older friends and family getting married, and all of them both attractive themselves and marrying someone gorgeous and fit as well, I cant help but start to feel jealous. I mean, I never thought I’d end up with an athlete or supermodel, but the idea of even an average girl being out of reach since, well, I’m way below average, has me pretty bummed out. I feel deep down I could be a great boyfriend/partner/SO/spouse etc, but it feels like the kind of relationship I want to have is both in sight but out of reach, save for waiting till my 30s for someone to settle “below their league” or barring a full Chris Pratt-esque transformation. Going to film festivals and stuff by myself is fun but it’d be more fun if I were doing it with my girlfriend, you know?

TLDR: I’m putting all the effort in but it still isn’t enough to get ahead of even where I was when I wasn’t trying to get a girlfriend.

Sincerely,
Trying My Best

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