I've said it before and I'll say it again.
Self-deprecation is not cute, attractive, or cool. It's become the fashion to call yourself "trash" and whatnot and to point out all the ways you fail at life or at "adulting", but that's really not something that will attract potential mates. If you think of yourself as a friendless, virgin, micropenis loser, then that is exactly how you will come off to people. If you introduce yourself with your faults, that's asking people to stay away from you.
Some guy on Reddit the other day was whining about how he's a virgin who has never been on a date with a girl, and couldn't understand why girls ghosted him as soon as he brought this information up (usually still while in the texting phase). Sam seems to think the same way.
Plus, yeah, he's not getting Mila Kunis or something. The Wallflower would be the absolute best he could do at this point. Also, someone this self-absorbed would be a shit dad, just saying.