The Times UK has published an excerpt from journalistic power-spawn Quinn Bradlee‘s new book, A Different Life. The book is about how Bradlee—-son to Sally Quinn and Ben Bradlee—-struggled with disability growing up, and also lost his virginity to a prostitute for $35 while on vacation in the Carribean with his parents.

The weird part about this whole thing isn’t that the brothel was called “Heaven’s Gate”; or that he was mysteriously driven there by a taxi driver named “Silky”; or that Bradlee didn’t even figure out what he was paying for until “she started to take off her clothes”; or that he was “glad it happened”; or that he immediately told his mother; or that his mother then dragged him back to the brothel to pick up his prostitute and test her for HIV because Sally Quinn “worries way too much, if you ask me.”

No, the weird part is that this hilarious little Carribean prostitution adventure is Bradlee’s way of introducing a much more serious topic: “Girls.” Bradlee closes out the chapter by wondering why he’s been unlucky with the ladies:

More than anything, I want a girlfriend. I think one of the reasons I have a hard time taking it to the next level with girls is because I had no contact with girls for much of my adolescence. Sometimes I think that I’m a loser, that I’ll never find a girlfriend, that I’ll be a nobody for the rest of my life.

I seem to have the worst luck with women no matter how hard I try. I feel they’re picking up some vibe from me that says I can’t handle a relationship, or I’m not mature enough to be in a relationship. Whatever it is, I am apparently doing something wrong. I’ve taken and followed all of the advice my friends and my parents have given me about dating, but it hasn’t quite worked out for me yet.

I have trouble with reading cues and I can never tell if girls like me sexually. If you’re having an intimate friendly conversation and a woman is smiling and you’re making her laugh, then you think that maybe it’s possible to take it to the next level. But, typically, the day after that kind of thing would happen with a girl, I wouldn’t hear back from her.

It goes on and on. Hmm, okay, perhaps Bradlee should first try skipping the prostitute story, and also, actually, any story where Sally Quinn completely freaks out. He might also pare down the six excrutiating paragraghs detailing why, specifically, women have never liked him down to, I don’t know, zero.

Or maybe I’m wrong: Maybe the “my mom’s crazy, I fucked a prostitute, women don’t understand me” tactic has worked out: Bradlee’s Web site says he’s currently in a relationship.