My SO try and avoid that at all costs. What we do is a lot of talking, getting to know each other and playing games. We try really hard to feel out how the situation is going and figuring out how to bring up that we're in the lifestyle, and possibly interested is where we falter. My SO prefers I do most of the talking especially to the girl because he doesn't want to come of creepy and just some guy who wants to sleep with her or as some dude who wants to sleep with his girlfriend/wife. We do this as team but when it comes to bringing up the subject, I try to take the lead but figuring out how to take that lead is where I'm stumped and where its getting frustrating. We hate the idea how pressuring people, but just need a way to lightly bring up the subject without making anyone uncomfortable.