I recently found myself with a new Match profile and a list of creeps to weed through. I think I found one worth meeting for a free drink, at least, but don’t know how to move the constant messaging to real life awkward conversation.
I live in the suburbs but all the guys I meet online live in the city. This one keeps telling me to let him know when I venture downtown but doesn’t tell me where in the city he lives or offer a time to meet. He hasn’t even asked for a phone number! What do I do?
Choosy in Chicagoland
Oh, Choosy. My dear, sweet Choosy.
Men are dummies, but so are we. I say this assuming that you are a heterosexual woman, of course, because I don’t hear a lot of gay men having this type of problem. They cut to the chase on dating apps, and I think we could all learn a lesson there.
This guy you’re talking to only seems interested if it’s convenient. Maybe he doesn’t have a car to get to the suburbs, but even that is no excuse to make you question what’s going on. (Having no car of my own to date a suburban being, I understand his hypothetical predicament.) Your profile makes it clear you live in a suburb, right? Then he can’t use that as an excuse to string you or the idea of a first IRL meeting along.
Damn it, a complete stranger should not bring you this much anxiety. It’s just dating!
In your next message, you need to be clear in your intentions. Tell him that you go to the city regularly as long as you have a good reason. If he wants to be that reason, he should offer at least a day of the week if not a specific time and place. Give him your phone number (a burner number is acceptable) and stop answering his messages unless he calls or texts like a human being of millennial age. Hell, you’re a modern woman, ask him out yourself, even!
The moral of the story is: you’re not star crossed lovers without options, so quit writing letters as though he’s off fighting for the Union.
What do you think, Dear Reader? Should Choosy ask this guy out or quit while she’s ahead?