I need some advice on a "first time" situation--her first time after a baby. I have a date Friday night with a pretty good friend whom I have been dating more and more seriously the past couple months. We aren't in love, but this isn't an FWB situation. I don't know if the relationship will be long-term or not. The girl is gorgeous: very cute, great body, I WANT her! But she's also a friend and I like her. We've been on a few dates but never been able to really spend a romantic ending together. We've kissed--even kissed passionately--but nothing more. I asked her to go on a "real" date this Friday and she told me I should book us a nice hotel room. She's a young single mother with a pretty young baby. This isn't just the first sex she's had since the baby was born; her last time was the day the baby was conceived. She had sex just once with a guy who was a total jerk and used her during a tough emotional time. She carried a child from this no-show father and now she's a single mom. She's dealing with insecurity about her post pregnancy body. ...and this will be the first night she's spent away from her little boy. (Her mom will be watching him.) She hasn't had any action at all in more than a year. I know she's horny, but I also know there are a lot of factors making her vulnerable--which makes it easier for me to screw it up. How should I play this? My plan is to play it by ear and depending on how she seems either: A. Gently but firmly take control and move right into sex. Probably in the dark (light a couple candles) to avoid any body self-consciousness. Face to face, kissing, slow touching, manual stimulation, missionary, lots of cuddling... Or B. Just snuggle for the evening, sleep together--partially dressed??--and see if we can move comfortably to intercourse (or at least some other fun stuff) in the morning. I'm undecided(,in either case) whether a shower would be a good way to explore her body and let her know I find her attractive--or if that's a terrible idea. And I don't know about condoms?? She definitely doesn't want to be pregnant again, and she's on the pill. But I'm not sure if proactively pulling out the condom communicates a sense of unease about her history? And where do I finish? Pull out? Aim it where? Yeah, I'm totally overthinking this, but... I want to take care of her because it's the right thing to do--but primarily because I want to have lots more sex with her. I figure getting this right the first time garuntees me a very satisfy sequel. Right?