Q. “I saw a friend of a friend on OKCupid and I’m kind of interested in her. Should I contact her through the site as normal, or should I go through our shared friend, or some other social medium? It might be more awkward if she turns me down through OKC, maybe??”
A. “You know, one of the things I love about doing this column is that so many of the questions boil down to the following cry: I like someone, help. Even though this is a technology blog! Even when you think you’re asking me about Netflix or G-chat or leaving your computer with a stranger, you’re really asking: but what about kissing, though? What about kissing.
OK, so: the important thing to remember is that nobody should feel awkward or embarrassed in this scenario or any (most?) of its potential outcomes. Like, you’re never going to actually live by that or overcome it in any way, but just REMEMBER it. Know that it’s out there, true and vaguely familiar. If you get turned down, you get turned down. No single delivery method of rejection is going to feel better than another. (UNLESS you ask out the Publishers Clearing House prize money guy right before he hands you a large check, I guess?)
I do think, though, that it’s better to go through your friend in some way, if you can. If your mutual friend is a good one, you can drop hints and try to get some group thing scheduled, just so you can meet this woman in a semi-natural state and get all that good intangible attraction information up front. For a lot of people, getting an OKC message from someone they know is going to provoke this knee-jerk reaction of “Why am I LIVING,” and generally you want to avoid that as much as possible in dating. Try going through the friend! If it doesn’t work, just send her a message. Oh well. Nobody feel awkward. Stop throwing up!”
- The rest of my FWD etiquette column is here.