Should I try to sleep with my best friend tonight?

Basically the story is this... Last year I met a girl and we talked for a bit, her and her boyfriend had just broken up and she was devastated. We ended up becoming really close over the course of a couple weeks and started sleeping together. About a week after that, her boyfriend got in touch her and said he missed her, made a huge mistake leaving her, all that stuff. They got back together but we continued fooling around for a couple months after that. Around September of last year she said she couldn't do that to her boyfriend anymore, which I totally understood and we went from I guess casual fuck buddies to just regular friends.

Anyway, even after we stopped sleeping together we remained really close and she's basically my best friend these days. We hang out pretty much daily, text each other all the time that sort of thing. Earlier this week her and her boyfriend broke it off for good. She knows I'm interested in her and we've talked about what would happen between me and her if she ever found herself single again. That conversation was about 2 months ago, but she said she would be open to having something more serious with me if that opportunity ever came up.

Now I already offered to take her out tonight just to get her out of her house so she wouldn't be stuck in her head thinking about her ex, and she said yes.

Should I try to press the issue tonight or just keep it friendly and casual for right now?

Updates:
Any way I can get a feminine opinion in here?

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Most Helpful Girl

  • I'd say keep it friendly and casual, otherwise she will think that you are only interested in shagging her.

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What Girls Said 0

The only opinion from girls was selected the Most Helpful Opinion!

What Guys Said 2

  • Sure. She either likes you back and you can begin a relationship or she doesn't like you and you can move on.

    Chances are she will give some speech about how she likes you but isn't ready. If she does this it is a bit of a bozo and what she wants is to keep you as a back up. She'll date some bozo but keep you as a back up. if this happens, get out.

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  • Keep it friendly right now if you're interested in a serious relationship. You don't want to seem predatory and only in it for the sex

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