This is kind of a complicated story, but what you need to know first is that I repel men. I don't know what it is, I think I'm kind of cute and pretty intelligent, but I have been on exactly one date in the last four years.
Anyways, so this story begins last Halloween when I went to my friend's costume party. At the party I met her husband's friend James (not his real name, FYI, I made it up to protect the innocent). I thought he was pretty cute and friendly but nothing happened and I went on with my life. Then in February, James started coming to my gym. It took me about a week to figure out who he was (he looked familiar but I couldn't place him). I told my friend I'd been seeing him at the gym, and she asked me if I'd said hi. I have a crazy good memory and remember almost everyone I meet, so I have come to know that it's better to just pretend to not remember someone than be the freaky girl who remembers how you were wearing a red shirt that time we were introduced to each other three years ago. Because of this, I had not said hello. We'd only had one brief conversation at the Halloween party, and I didn't want to creep him out. My friend assured me that he had the same type of memory and probably recognized me, but I still didn't say anything to him.
Around my birthday in March, when I was sad and lonely and realizing how OLD I am, I signed up for Match.com. And who should be a 100% match for me? James, of course. I thought about messaging him on Match with a "hey aren't you so-and-so's friend and didn't we meet at their Halloween party?" message, but I could never get the wording right.
Now it's the end of July, and I've decided I think he's really cute and I'd like to talk to him. We are at the gym at 11 am (when it opens) every Sunday together. And I mean EVERY Sunday. I've missed three Sundays since February for other obligations, and I think he's missed maybe two or three as well. I know that I go at that time to see him (because I am a sad, pathetic person), and I catch him looking at me sometimes, but I don't know how to approach him. He's always got his headphones in, and I don't want to disturb his workout. Do I send him a message on Match.com? Talk to my friend about casually setting us up? What if he's not interested? I'll have to switch gyms, because I'll die of embarrassment if I every have to see him again.
I'm so hopeless with guys, and I need some Jezzie wisdom on how to approach him.