So, there is this girl. She is cute, we hangout a lot, and I like her. But she is also my best friend and current roommate. We have known each other from high school and when we first moved in together she had a boyfriend so I never really considered hitting on her. But a month or two back, her and her boyfriend broke up and now we have been hanging out more. I am tempted to make a move but worried it could back fire and then I am stuck with an awkward moment and it could ruin our friendship and living situation. Any advice? Thanks.

do you really like her or just want to bang her? do you think she might like you?

Nothing great is going to come without a risk. Yes it may back fire, yes it may make things awkward if it doesn't work, but thats the risk we all take when we want something that could potentially be worth it. If there was no risk, you either wouldn't be invested, or you would've done it already.

So you have to ask yourself.. Is the risk worth the reward? If you believe so, then go for it.

However, I would advise against it.. Its your best friend and roommate.. If you're asking about her then you probably don't have too many options with women. So i'd say, no for the sake of your living situation, but you know it better than me.

If you're putting all of your eggs in this basket hoping to get this one girl.. Definitely don't do it.

Now if you see this as a positive step whether you succeed or fail to become more confidence/attractive when faced with risky situations.. then go for it. Take the potential temporary loss for the long term gain.

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Thanks for the advice. I am thinking it may be more than just hooking up and I think I may really like her. I am trying to see other girls, I actually am going out tomorrow with someone else. If I were to approach her with this, how would you do it? Slowly start flirting more, just tell her how I feel, make a move...?

Escalate next time you're together and see how she reacts...

Don't tell her you like her. Don't tell her you want to date her... If you do either of these, you're done.