Ask Rob Returns! Just Do It. Or Not.

From time to time at DC Style Is Real, we feature advice from a panel of experts.  Not just random guy-at-the-bar advice, but empathetic, thoughtful advice which shoots right to the heart.  Now get ready for some angst, high school style.
There’s this girl I want to ask out.  We run in the same group of friends, but I can never get any time alone with her.  I think we’d get along and I’d like to ask her out…what should I do?
First and foremost, understand that there’s always a possibility that your friendship could implode as a result of your pursuit.  No matter how hard you try, there’s just no telling how people will react to the situation, including yourself.  For example, the girl could freak out, tell everyone you were creepy, and never show up again.  On the other hand, maybe you two develop into a relationship, only to result in a breakup that leaves both parties devastated and friends choosing sides.  Life is unpredictable and there is always risk.  However, it sounds like you really like her, and you aren’t content with just being friends.  You are looking for romance and that’s great.
So obviously, the direct way would be to get her contact information and simply ask her out. Right now, I would caution against that.  Given that you haven’t had a chance to talk to her alone, you probably don’t have any idea about your compatibility and chemistry.  After all, it’s one thing to chat and hang out amongst a group of friends, and another to talk one-on-one.  Furthermore, I’m guessing that you are not on her radar either, and she only thinks of you as a friend.  Asking her out now may make her reluctant.
Therefore I would recommend you get more intentional about talking to her and getting to know her in your group.  Start sitting or standing near her and strike up a conversation.  Flirt with her and use that charming wit of yours, and see if she responds.  After you do this a few times, evaluate how things went, and see if you were able to generate any sparks.
Meanwhile, you have to constantly be aware of group dynamics. I doubt that you are the only guy interested in her.  On top of that, there may be other girls interested in you, you handsome devil, you.  You may be stepping into a complicated emotional chessboard filled with attraction, competition, and jealousy.  Move with care and precision, and treat everyone with courtesy and respect.
If, after all this, you feel there is good chemistry between you two, then go ahead and ask her out.  It is best to do so with confidence.  If you can’t do it with confidence, well just do it anyways, and you will get brownie points for having the courage to do so. Good luck.
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