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The fog is finally lifting on the bizarre situationship I’m in (which, honestly, is a letter for another day). As I prepare to date again, I wanted to ask if you had any advice on how to ask someone you’ve only briefly spoken with before out on a date?
Context: Last fall, I downloaded Tinder when I was feeling particularly lonely (instead of communicating my feelings to the situationship guy). I ended up actually having a nice chat with a guy who seemed interesting. We’d actually followed each other on Instagram a while ago, but had never really talked. Tinder presented that opportunity somewhat naturally.
The conversation faded after a few days, as they tend to do. I no longer have the app, but we still follow each other on IG. I want to ask him out and see if there’s something there, but I don’t know how to approach it. Do I casually strike up a conversation in his DMs? Would it be weird to just hit him up out of the blue and ask him out on the first message? Do I redownload Tinder, make a new account, and try to match with him again to message him there?
I know I’m young and have so many years ahead of me, but I think I am more of a relationship guy and it already feels like doors are closing, so I don’t have the time to slowly wriggle my way back into this guy’s consciousness by strategically liking posts and stories for six months before talking again.
Help me, Papi!
Hey there, TT!
Yes, please do send me a letter about the situationship. There’s no guarantee I’ll answer it. I just collect them. I’m like Smaug from The Hobbit, but instead of gold I have little gay dilemmas.
Anyway, I love that you’re more comfortable writing in to your favorite advice column about asking a guy out than you are with shooting him a quick “how’s it going?” over Instagram. Assuming, of course, this is your favorite advice column.
I’m your favorite, right? Haha.
Am I your favorite?
Are you still there?
Haha where did you go?
Sorry, that was a joke about how some Instagram DMs go. You know what I mean. We’re probably all that person to someone: just a bunch of “seen” flame emoji reactions. Maybe some of them get “hearted.” That’s exciting. That’s something. That’s a little treat.