Alright, as promised, here's how the conversation went. A little weird at a couple points but it seems to have worked.
Me: Hey, I'm gonna be blunt with you for a second, can you handle that?
Her: Okay, go
Me: I've got to know, what's keeping us from being friends with benefits?
Her: I don't like being friends with benefits
Me: And why is that?
Her: Because someone always ends up caring and getting jealous and it's never me. Then it leads to drama and turns into why can't we just date and then feelings get hurt.
Me: Haha it's funny that you say that because I though I was the one who ends up not caring. I'm not that type of guy. (Looking at this now I probably could have said something along the lines of "You watch too many romantic comedies" or something to that effect.)
Me: It's cool if you don't believe me. But I know what I want, and I keep my sh1t in check.
Her: Ya then I get bored and like someone else more than you and move on because we never had a commitment together then you get mad and your feelings get hurt.
Her: It'll happen.
Me: I can guarantee that wouldn't happen. Like I said I'm not that type of guy. I just want to have some fun and thought that you'd be on board with the idea.
Me: How about this, try me. Let's have some fun and if you get bored or you get weird about it, we'll stop, problem solved.
Her: I thought we were kind of already doing that..
There was some more after that, nothing noteworthy. Essentially just setting up a time to get together again, which is looking like next week. I know the conversation could have gone a lot smoother. Any suggestions on what I could have done differently?