So I'm sitting at this restaurant/bar type thing in the city with my friend. Both of us are pretty bored, drinking, having a good time, when all of the sudden, about 5 OUTSTANDING, classy looking women come in and have a seat a few tables down. The restaurant is nearly empty. We notice they order a round of beers. My friend and I discuss it for a while and decide to buy them another round. First mistake of the night: we waited at LEAST half an hour before making our approach. The waitress came up to us after that half an hour and said they asked what our names were. We're both somewhat of shy guys, but I took the initiative and dragged our asses over to their table. Small talk was made. Very small. Two of them were lesbians who were "in a serious relationship," but I asked one of them about their friend who my friend and I were talking to the most (who wasn't at the table at the time), and she said she was into us (can't remember if she mentioned one of us specifically). My friend was the one sitting next to her, so I figured I'd let him go for it, kind of as an excuse not to do it in fear of being awkward then getting rejected, but also sticking up for my man. More fucking small talk. After about half an hour of this, they said they had to go, and that's exactly what they did. The one girl who was "into" us gave us her number. She never picks up.

Moral of the story: go for it while you have the chance! If you have the confidence to make it far enough to the point to where you're actually TALKING to her, you need to KEEP GOING! DON'T give up! If you mess up, at least you can tell yourself you tried, and that's a lot less pain than not trying at all.