I am 28 and a former incel, and I’ve been working on my issues for over a year now. I went from a point where I had no friends, just sat in my parent’s basement and worked/played video games/bullied people online, to a point where I volunteer a lot in my community, go to local events, am part of a bunch of clubs and organizations, and have a small group of friends I hang out with regularly. I am really ashamed of the beliefs I held earlier. I don’t think I ever acted on them in person but I was definitely a toxic bully in a few different online forums. I still have a lot of self-esteem issues because I’m 260 pounds and look like a frog, but I’ve been on two first dates from dating apps, where everything is based on looks, so at least a few women find me attractive. I have also started to understand that appearance is not the sole reason for most relationships (or even the primary reason). However, due to my past, I am woefully behind in managing healthy social and romantic relationships.
I volunteer for an organization a few weekends a month where we make science and math fun for elementary school kids. After the kids leave we usually go get coffee or something together. Once we were invited to someone’s party. I don’t drink. One of the other volunteers, who’s 25, is also very shy and we’re friendly with each other but I don’t really know her too well. The party was her first time drinking and it didn’t go well for her. The night ended with her passing out after vomiting, breaking her very thick glasses which she is virtually blind without, slipping on her puke and landing on a table with her face and hair in someone’s drink, calling herself ugly, and sobbing in my chest. I was the only sober one there, but my tipsy friend and I were able to get in contact with her roommate and we drove her home.
Since that incident, my friend keeps telling me that she’s looking at me differently, and is obviously attracted to me and that I should ask her out. I am completely oblivious in social situations and I don’t know if that’s true. The only things I can think of are when she asked if she could come over to my apartment to watch a horror movie I said I liked (which she did, it was fun), and when she said something to me in private out of the blue about wanting to be a mom before she turns 40. Our organization doesn’t explicitly have a policy against volunteers dating. She’s very cute, we share a lot of interests, and I wouldn’t mind being in a relationship with her, but I feel like if I asked her out and she rejected me it would make our relationship worse, especially since we work with the same set of kids and so work together a lot.
Other people besides my friend have started to ask me if I’m going to ask her out, which makes me think that I must be missing something obvious. She knows that I used to have problematic beliefs, but I don’t know if she knows that I used to be an incel. If we are actually both attracted to each other, she would not be the person to ask me out because she is quite shy and non-confrontational. I am also shy and non-confrontational but I am prepared to ask her out. Should I ask her, though? I am prepared to take no for an answer and go back to our regular lives, but how should I deal with it if she finds me weird or strange after rejecting me?
—Do I or Don’t I