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I think I want to date my best friend.


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I've known this girl for over a year and a half. Let's call her B. She started dating my friend and roommate and she and I developed a really close, and completely, totally platonic, friendship. There was no interest in anything more than that from either of us.


In May, my friend broke up with B. It was obvious that it was coming for a long time. The two of them just weren't compatible in many ways. Shortly after that, I found myself thinking about B as maybe more than a friend. And then a month or two ago, one of B's best friends told me that B had feelings for me that went beyond friendship, and that whenever the two of them discussed me and B possibly dating, she would get giddy. I have to say that there are a lot of signals coming from her. And if I weren't so dense, they'd probably be glaringly obvious.


I sometimes think it would be the easiest thing in the world for us to start dating. We already hang out all the time. She's always there for me and obviously cares a lot about me. I know she's been talking to a couple of guys online, so I'm worried that maybe she's given up on me.


How can I broach the subject without making it weird and awkward? Should I just maybe start being more, I don't know, affectionate? We'll occasionally hold hands (initiated by her). Should I start initiating things like that? This is so weird to do with your best friend.



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To me it sounds like trouble all over the place, id give a red flag on this one. Its all too coincidental, think about it, she seemingly can have everyone she want, and she rather dated the other guy then you in the first place, meaning you are already a second choice, even if she dated you, she is just waiting for someone else to come around that is better then you and dump you the moment that person appears in her life. I don't like the signs of it. You are just like a fish that wants to bite the bread with a hook on it, it all sounds too painfull for me, and you being dense (as you stated) are probably not overlooking all the details in the situations which you actually should do at all times.


Skip this one and get a girl who considers you as her nr.1

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I disagree. The OP's roommate started dating her, and she didn't even know the OP before that. Why would she pick the OP when she's dating someone else already? Loyalty to a significant other is an admirable quality. I don't see a red flag there.


Anyway, she's over the roommate now, and free to start looking at other guys. She's obviously ready - she's looking online. OP, that means one of two things: you waited too long and she's moved on, or she's open to move on. I'd let her know you're interested, and soon. Ask her out. Since you already hang out a lot, call it a date. Make it pretty clear what you're doing. Don't confess your undying love or anything, but do make it clear that you want to date her.

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