Ask Dr. Nerdlove by Harris O'Malley

Why Do I Still Struggle With Dating Women?

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.


Trying My Best

DEAR TRYING MY BEST: Ever want to know the best way to make it impossible for someone to win a footrace, TMB? Ask them if they pump their opposing arm with each stride or the arm on the same side, then watch them trip over their own feet as they try to figure it out.

This is a common issue; there are things that we’re able to do without thinking, but the instant you start thinking about the mechanics of it, you fall apart. It’s the Centipede’s Dilemma: everything was going great until someone asked the centipede how it kept all its feet in sync. This is what happened to you. You were far less conscious about the image you were projecting and you weren’t concerned about trying to get people interested in you and so you were able to be real with folks. You had more genuine connections, you presented yourself in a way that was authentic and attractive and people responded to that.

Back then you were able to do more because you didn’t care and weren’t dependent on the outcome. Now you you do care… well, now you’re aware of the pitfalls. Like Wile E. Coyote, you were just fine until you looked down and realized you’d ran off the cliff.

Now that you’re more aware of women and wanting to find a relationship… well, now you’re trying to focus on a dozen things at once and you’re tripping up over your own feet. This is actually an incredibly common issue among folks who’re trying to get better at dating, or any skill, really. When it comes to learning any new skill, whether playing a musical instrument or learning how to date, you go through four stages. In the first stage, unconscious incompetence, you’re unaware of what you don’t know; you’ve never encountered this before and so you have no idea what to expect. The second stage is what’s called “conscious incompetence”. This is also known as the Pain Period, because you’re getting smacked in the face at just how little experience you have with this. This is the part where you’re just painfully aware of all the mistakes you’re making, how little you understand and it feels like you’ve somehow regressed in skill level. This is also the part where most people give up because… well, because it sucks. It’s a humiliation conga, where it seems like you can’t do anything without making twenty mistakes in the process.

But here’s the thing: as a wise man once said: sucking at something is the first step at becoming good at it. You’ve got to grit your teeth and put in the conscious, deliberate practice in order to get to the next stage: conscious competence. This is the stage where you know what you’re doing, but  you have to devote all your time and attention to making it happen. This stage can be a little nerve-wracking because you’re aware of how well you’re doing and how many steps it takes to make things happen. But the more you work at it, the quicker you turn the conscious awareness of those steps into muscle memory. At that point you enter the final stage: unconscious competence, where you’re able to do all of this without thinking.

So the frustration you feel is understandable, but natural. It’s part of the process of learning how to consciously do the things you used to be able to when you didn’t care. But the difference is that this time around, you’re going to be able to choose when and how you do this.

Where you have an advantage, though is that you’ve experienced something that other people have to work for years to learn: issues like your weight aren’t nearly as important as how you make people feel. Looks and presentation count, but what counts the most is how people feel when they’re with you. So while working out and getting fit is good and something you should keep doing, it’s not the end-all, be-all of attraction. Being big doesn’t mean you’re “below average”. Women like a wide variety of body types, my dude. Some women like ’em ripped with more cuts than a David Fincher film. Others like burly bears and dad bods. So while you may not look like one of the Marvel Chris’, that doesn’t mean you’re unattractive, or even that you’re somehow “stuck” dating women “beneath you”, whatever that means. Focus on dressing well and connecting with people on a genuine level and making them feel good when you’re around. You’ll find that there’re awesome women out there who like you because you’re big and you look like a hug.

Grit your teeth and put in the work, my man. You’ll get through to the next stage sooner than you realize. And that’s when you’ll start having the success you’re craving.

Good luck.

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