Ask Anyway

There’s this moment where you’re sitting on your bed, scrolling, telling yourself you can’t talk to anyone because you’re too fat, too tired, too wrecked from sitting at a computer all day. As if appearance is the actual barrier. As if the problem is your body and not your nerve.

Jason apparently made a video about this—about approaching women as an overweight guy, and it working because he had the confidence to actually try. And that’s the thing that keeps surprising me: it does work. Not because he’s secretly attractive, but because he showed up without the commentary running in his head about why he shouldn’t be there.

The video was probably meant to be motivational, the kind of thing you watch seventeen times hoping it rewires you into someone who can just walk up to a girl and ask her out. Steffi from afternoon class, whoever she is. Someone you’ve been thinking about for years but never spoke to because you were too busy manufacturing reasons why it wouldn’t work.

Here’s what the list at the end reveals—works for skinny guys, muscular guys, short guys, tall guys… The specificity is almost absurd. It’s saying the barrier isn’t body type. Never was. It’s the moment you decide to anyway, despite whatever narrative you’ve built around yourself. Despite the certainty that you’re disqualified. A fat guy, a thin guy, a tall guy—they all have different insecurities, different versions of why not me. The guy who finally talks to someone anyway is the one who doesn’t wait for those to resolve first.

I don’t know if I’m convincing myself or if this is actually true. Probably both. Confidence sounds like such a stupid answer when you’re the one sitting there, but it’s the closest thing I’ve found to an actual answer. It’s not be yourself or any of that hollow stuff. It’s more like: accept that you’re nervous and do it anyway. Accept that you look like whatever you look like and ask anyway. The combination is less explosive than the self-help version makes it sound, but it’s also less impossible.

The thing I think about is: how much time did I waste waiting to be different before I could try? How many years of Steffi sitting there, approachable, while I was manufacturing certainty that it would fail? I don’t even know if that’s regret or just information. Either way, it’s not going to happen while I’m thinking about it.