¡hola papi!

‘How Do I Ask Him Out?’

Illustration: Pedro Nekoi

This column first ran in John Paul Brammer’s Hola Papi newsletter, which you can subscribe to on Substack.

¡Hola, Papi!

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 having a nice chat with a guy who seemed interesting. We’d followed each other on Instagram before that, 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 re-download 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!

Timidly Tindering

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.

I highlight this, TT, to remind you of how low the stakes are. There are only two things to accomplish: Express interest. Avoid desperation. That’s about it. You’re not even hitting him up out of the blue! You can just ask how he’s been and if he wants to hang out.

There’s a chance, of course, that he will leave you on “read” or give you a generic “maybe perhaps at some point” kind of response. That’s fine. There will be other people to go on dates with. But there’s nothing wrong with putting yourself out there and trying to establish a connection.

I think the fear is that we’ll be rejected, or that we’re doing something creepy by being “too forward.” This makes sense. Those are vulnerable acts. We’re sticking our necks out. This stuff is an art, not a science. There’s simply no accounting for how others might react or how we might be perceived. I feel that. I get nervous about it too.

A friend once gave me great advice on this front. She told me to behave like it’s normal for people to be attracted to me. That doesn’t mean everyone will be into you. It means that you don’t have to act like this one person rejecting you is the end of the world, or that you have to put on airs, or try really, really hard.

It means there’s nothing unusual about someone wanting to get to know you, or finding you interesting. It’s quiet confidence that things can work out. You can be straightforward and direct because this isn’t a test to see if you’re a worthy person or not, and you can accept “no” as an answer because your self-esteem doesn’t depend on a “yes.”

Be calm. Be confident. Be flexible. Strike up a conversation and ask if he wants to get together. Be okay with his response. It’s much simpler than re-downloading Tinder and trying to match with him again.

Also, before I go, I’m not sure where you’re at in life where you have several years ahead of you but also feel like the doors are closing. What doors? Sounds scary. Have they already closed on me? Am I low-key in a room right now? Is it a room with a bunch of old people, people who will never find love, or some combination of the two? Can we not just date each other? Here in this room?

I guess I have questions of my own.

Con mucho amor,

Originally published on April 5, 2023.

This column first ran in John Paul Brammer’s Hola Papi newsletter, which you can subscribe to on Substack. Purchase JP Brammer’s book Hola Papi: How to Come Out in a Walmart Parking Lot and Other Life Lessonshere.

‘How Do I Ask Him Out?’