By Fenrir.Weakness 2013-11-16 22:24:13
Late chime in for giving Mag woman advice...
From personal experience I have always known/been friends with women before I dated them. They tend not to get offended if you do ask them out. Some times a semi-awkward moment can occur, but it will usually fade if you are decent friends anyway.
So, million and one reasons to do it... and none that I can think of other than baseless fear of being rejected. If she's friends with you and you have been talking often, she likes you at least on some level, romantically or not doesn't matter. I vote sooner than later, otherwise you risk someone else stumbling into the picture.