Unfiltered Story #47733

(My boyfriend is the brother of a close friend of one of my best friends. I really like [Boyfriend]’s sister and am on friendly terms with her, but we’ve never been exceptionally close and have really only spent time together in the presence of [best friend] and/or [boyfriend]. [Boyfriend] is telling me a story about something that happened years ago.)

Boyfriend: So I had [sister] and [two female friends] in my car, looking for one of those seasonal Halloween shops. We kept passing where we thought it should be, so we pulled into random parking lots and turned around three or four times on [street known for having a high rate of prostitution]. I got pulled over for suspicious behavior, and when the cop saw three women in my car, I’m sure he thought for sure I’d been collecting hookers!
Me: Oh, man, I would totally buy your sister as a hooker! [Pause, as boyfriend stares at me, baffled]. Oh, not in a sexual way at all! I just think it would be fun to see all of the crazy stuff we could do. [Best friend, who is a male and gay] and I would come up with all sorts of hilarious, ridiculous adventures! [Best Friend], [My Name], and their Hooker. It would be a great sitcom!

(Boyfriend somehow follows this insane logic and starts laughing with me as we think of the non-sexual adventures his sister and I would embark upon if she were a hooker. Several weeks later, I’m at [Boyfriend]’s house, with his sister AND HIS MOTHER)

Boyfriend: [Sister], [me] said she would love to buy you as a hooker!

Sister: Um….

Me: In a completely non-sexual way! Just to go on crazy adventures with [Best Friend] and me.

Sister: Oh! You could start paying me now…

(His mother still likes me for some reason)