I let an older man buy drinks for me and my date.

  • By: Amanda Coscarelli

This story has been submitted by a LOOP reader…

I swear I wasn’t planning on becoming that person—the one who lets some older guy at the bar bankroll their night. I always thought I had too much pride, too much feminist backbone, too much… I don’t know, self-respect? But pride melts fast when the cocktails are $18 and the night is young.

The night started with good intentions. My date, Lila, and I had decided on a “nothing fancy, nothing serious” kind of evening. Just two semi-functional adults trying to have fun without pretending it was anything else. We picked a bar that had the perfect mix of dim lighting, decent music, and bathrooms you wouldn’t be afraid to sit down in. A luxury in the city.

We slid into a two-top by the bar, already buzzing from the shot we’d taken in the Uber. I liked her immediately—too much, probably. She had this laugh that made you want to confess things, like how you hadn’t folded laundry in three months or how you cried at that one commercial with the dog and the aging owner. We’d only been talking for 15 minutes when I felt the shift—that sensation that someone is studying you from across the room.

Enter: silver hair, linen shirt, gold watch. His age: somewhere between “experienced” and “eligible for early boarding.” He wasn’t creepy, just bold in the way men who’ve survived several eras of flirting tend to be. He raised his glass when our eyes met, and I gave him that half-smile that means I see you, but I also see the bartender, so don’t get ideas.

But he got ideas anyway.

He wandered over during a lull in the conversation, leaning a forearm on the edge of our table with the confidence of someone who definitely owns property.

“Not to interrupt,” he said, smiling at both of us evenly, “but I have a feeling the two of you deserve a better drink than whatever you’re sipping.”

It wasn’t even a line—it was more like an invitation to let the night unfold. Lila raised an eyebrow at me. I bit my lip to hide a grin. Maybe it was the tequila settling into my bloodstream, but he seemed harmless enough, and most importantly, we were almost done with our overpriced cocktails.

“Sure,” I said, surprising myself before he could surprise us. “Why not?”

He signaled the bartender with that effortless grace men of his generation have, the kind that says they still think bars are places to start relationships, not places to avoid eye contact. Three drinks arrived—something with mezcal, citrus, and a rim that tasted like fancy salt. The kind of drink you only order when you’re not the one paying.

We’d only been talking for 15 minutes when I felt the shift—that sensation that someone is studying you from across the room.

He didn’t hover, which made me like him more. He paid, toasted us, and retreated back to his seat like we were part of some unspoken social ritual he’d mastered long ago.

Lila leaned in, whispering, “Are we… sugar-babies right now?”

“Only if we get a second round,” I whispered back.

And of course, we did.

 

Round two came with a wink. Round three came because Lila invited him to sit with us, insisting it was “the sociable thing to do,” though I suspect she just wanted more stories from him. And he had them—wild ones. A whole past of travel, failed marriages, successful divorces, impulsive decisions, lessons learned too late. He talked like someone who’d lived many versions of himself and wasn’t ashamed of any of them.

 

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Somewhere between rounds three and four, I realized something unexpected: I wasn’t uncomfortable. I wasn’t performing. I wasn’t pretending. I was having fun. Real, uncomplicated, free-drink fun.

I suspect she just wanted more stories from him. And he had them—wild ones.

The night didn’t twist into anything scandalous. There was no proposition, no awkwardness, no inappropriate comments. He bought drinks because he wanted company. We accepted them because we wanted a good story.

When he finally stood to leave, he patted the table gently. “You two made my night,” he said, genuinely. “Enjoy the rest of yours.”

After he walked out, Lila and I sat there, sipping the last of the mezcal, giggling at the absurdity of it all.

“Should we feel bad?” I asked.

She shook her head. “He spent money he clearly had. We had a good time. And nobody owed anybody anything. That’s basically utopian nightlife.”

She had a point.

So no, I didn’t feel bad. I felt… buoyant. Like for one night, the city wasn’t trying to drain me. Like sometimes you can let go, let the world be generous, let yourself be the kind of person who says yes to free drinks—ethically, consensually, and with a date who finds the whole thing equally hilarious.

And honestly? I’d do it again.

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