re: Strangest conversation you’ve ever had

I had a roommate my freshman year of college. I made the unfortunate mistake of giving him a ride somewhere (don't even remember where). I still remember stopping at the red light of Ben Hurr and Burbank when he started to ask me what I thought of my stepsister. This (now former) stepsister was ugly as shite, kind of overweight, and just 'crusty' looking. He then proceeded to ask if I would ever have sex with her given the chance. I think I remember him saying "Oh yea I'd hit it if I could and was in your position" and "Yea I think she's pretty hot, don't you?" While I knew he was fricking with me and knew I was getting sick just thinking about it, he kept persisting hoping I would budge throughout the entire 20 minute ride. Most uncomfortable conversation I've ever had. To this day I remind him of how god damn awkward that car drive was. He lurks on here. I hope he sees this lmao.