#319: Captain Awkward Writes Your Casual Encounters Ad

Dear Captain Awkward, I'm a single straight guy in my early 30s. I'm also a virgin. (Or at least I identify as one. I wouldn't quibble with anyone who'd say I'm not. I have some limited experience receiving oral sex, for example.) I'm far from the negative virgin stereotypes, I think: I have plenty of female friends, I have … Continue reading #319: Captain Awkward Writes Your Casual Encounters Ad

Reader question #107: Can friends-with-benefits work? (A qualified yes).

Dear Captain Awkward, It was perhaps my hookup starved, commitment-phobe, idealistic and naïve side that encouraged me to start a Friends With Benefits thing. Obviously there was the consent of The Friend, but prior to our first, drunken "Oh, what? We're making out?"-night that began FWB, I had given the whole concept some thought and … Continue reading Reader question #107: Can friends-with-benefits work? (A qualified yes).

Reader Question #21: Why don’t my friends-with-benefits like being told that they are friends-with-benefits?

Dear Captain Awkward, I have just discovered your blog and I love it for many reasons. One of them is: I have somewhere to ask this question! I am a young, single, straight, cis woman. In my capacity as such, I met a man a while ago -- and by a while ago, I mean, … Continue reading Reader Question #21: Why don’t my friends-with-benefits like being told that they are friends-with-benefits?