Should I try to date my best friend

My best friend (girl) is awesome. we constantly hang out and she often flirts with her comments and body language. we've only kissed once and she always talks about me when she gets drunk which is very seldom. We never argue and always have stuff to talk about we never get the awkward silences. We both date around a little with other people but never get serious. she sometimes tries to hook me up with other people but she knows that it won't work out and when I do hang out with girls she act somewhat jealous. there's nothing really wrong with me in my opinion, I'm not a 10 out of 10 but I'm in the top of the pile and I'm not annoying or obsessive, I'm the chill kind of guy that leads a very active life and succeeds academically. She is the girl that hangs out with the popular people every now and then but doesn't enjoy it. She normally keeps to herself. She has just a handful of good friends and isn't bitchy. Her hobbies are similar to mine and I'm involved in about half of her everyday activities, not that we hang out everyday (2-3) times a week. I've been wanting to ask her out in a way that if she says no everything will be cool. We're such great friends but I don't want to miss out on what could be one of the best decisions I've ever made but it's also definitely not worth losing her as one of the most awesome people that I've ever met. How can I ask her or should I even ask her at all.?

Thanks a ton - anonymous billy bob


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Most Helpful Guy

  • Well I dated my best friend and I was totally in love with her. Well when we were very younger she always told me her dream was to be asked out in summer rain with a rose and so on. I waited until the right time and I did it. Went on the knee the whole nine yards.hehe. But what I am saying is that you know her and know what she likes. I say go for it. It could be the best move you ever make. If you don't you could live the rest of your life wondering. And believe me it ain't a nice feeling.

    Best of luck dude!

    Ciao Ciao

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What Girls Said 2

  • If her feelings aren't the same towards you, then you stand to lose a best friend, but a lot of strong and solid relationships start out as best friends. Can you tell her anything in the world and talk to her nonstop for hours and then realize that hours has passed by and to you it only felt like 30 minutes? Then you feel sorry that you have to go? Ask her out fro coffee something like that just the two of you and tell her you need her advice.as a friend and ask her first if its ok to ask her as a friend anything without losing her as a friend? she should say OK! if she is a friend indeed! Then tell her the problem. that you have a friend that you really like and you don't want to lose them as a friend but you believe that there's feelings developing for this friend that is more than friendship because you obviously have chemistry. see what she says. her answer will tell you how to proceed. if she says just ask her. then ask her then and there. if she says well you might lose her as a friend. then take the hint and keep your friend and find a another girl to date. GOODLUCK and God Bless.

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  • Uh.well,talk to her about it,if you're best friends,she'll totally get it.And it sounds like she likes you too.But I could be wrong,so no blaming me if I'm wrong,okay? But if you don't want to take a big risk, just talk with her about dating and see how she reacts.Or you could even just say that you're "looking for the perfect girl who." then just describe her personality, and if she's not getting it,add in something that she did like."and a girl who laughed so hard she fell off a chair."or blah blah blah.personalize it.well.Good luck : ]

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What Guys Said 1

  • I'm engaged to my best friend we met in kindergarten, the hardest part? Knowing that if for some reason now it doesn't work, I am losing my childhood best friend. The best part is the look that you get when you say you met your wife in kindergarten, this is really a choice that you alone have to make I have tried dating friends in the past and lost them because something happened, but talk to her see where she stands you may have already met your wife and she's waiting for you to make the move.

    best of luck!

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