Well, I've just run into a situation that I'm not sure how to approach. I've been using free dating sites and apps because, well, why not. Worst that'll happen is that I just never talk to the person again. Wrong!
I've frequented a bar a block away times a week for the last several years. There's a very attractive, but more importantly, kind waitress there that I would ask out in a heartbeat. That is, If she didn't work at a place I go to frequently with my father.
A friend of mine went "SURPRISE" and apparently made an account for me on match.com because he thought that my dating experiences have been amazingly awful (which they admitting have.) I couldn't exactly tell my friend he was an idiot for wasting money on a site like this, so I said "sure, thanks, I'll use it." So I do, make a profile, follow all the instructions, and it matches me up with 10 women.
The very first match, with a 100 percent match rate, is the waitress I see multiple times a week. It's definitely her. I match everything in the profile except body type (I'm a bit chunky, but I've never found this to be a problem because I'm comfortable with how I am. Plus I'm losing weight at a healthy pace, I'm happy with myself.) I know she had a huge jerk boyfriend that she broke up with, which is obviously why she's on the site.
Now, the obvious thing to do would be to pretend I never saw her profile, which is still questionable because I'm fairly certain she'll see that I saw her. As much as I would love to "just ask her out already," I don't want to ruin my favorite bar if this becomes a disaster. I think the best thing to do is to send her an innocent message like "hey, small world! I hope you're having a great day!" or something similar.
Any thoughts or advice?