Actually, this is a girl I've known for a long time. Her BFF used to have a crush on me when we were in high school. We're friends on facebook, and I could always write her a note asking her out... but that's kind of lame.
Background: About 2 years ago I saw her one night from a distance, and then sent her an email asking her out for coffee, and she said sure and gave me her phone number.
We talked on the phone one night. Next day she sent a txt and said she was with some friends at a bar/rest near where I live, and told me to come. When I got there, she had saved a chair next to her, but there was this guy sitting on her other side and I noticed something fishy about the whole thing.
We talked for about 30 minutes (I knew the guy from before, so we also talked), she asked me about a lot of things, and when the time came to pay the bill, the guy sitting next to her paid for both of them. They left together.
I wasn’t 100% sure if they were a couple, so I called her a couple of days later, asked her what she was going to do that night. She said she was going to X place with some friends. “Wanna come?” I was going there with my friends anyway, so I told her I’d meet her there.
When we got there, I saw her hanging with her friends, and this guy was among them. So they definitely were starting to go steady. Not sure if she wanted to make him jealous with me, but I don’t like to play those games so I never called her again.
I think they dated for a while, but I’m 90% sure they’re not together anymore.
So now I have a couple of choices. I could send a PM on facebook and ask out again (even though I’m not 100% sure if she’s single), but I already did that and feel it’s kind of lame.
I could also wait until I randomly meet her somewhere, strike up a conversation and ask her out. But who knows when that will happen.
Or, I could make that random meeting happen sooner rather than later by paying a couple of bucks to a PI. Then at lunch I would say hi, and if I don’t get a chance to ask her out then and there, the facebook PM wouldn’t seem so creepy (something like “Hey, really nice to c u! Is your number still the same? You still owe me a cup of coffee” or something like that).