The Longest Shortest Time · Hillary Frank | Realm

LST FAVES: There's Something About Andy

December 3, 2025·41 min·3 clips
Andrew deliberately torments Peggy with engagement puns all night at the Olive Garden until she cries loudly in the packed restaurant.
The setup is almost too ordinary. Hilary Frank frames the clip as an archive favorite, then the story drops into a memory about wanting a milestone so badly it is hard to hide. Dinner is meant to feel fancy. For them, at twenty, that means Olive Garden on a packed Friday night, with one person dressed for possibility and the other teasing every loaded word. The joke keeps going. Commit and engaged land in all the wrong places, and the guest remembers getting angrier as the meal turns into a public test of patience. Then the menu hits the table. She starts crying loudly in the restaurant and tells him she is still hot enough to get somebody better than him if he is not going to do this. Andrew tries to move things along. Even in the car, while she is too upset to drive safely, he keeps circling back to the commitment puns. It is cruel enough to be comic, and comic only because time has passed. She pulls over to calm down. By the time they reach his parents' house, her anger has hardened into a promise that she will see him again, never. He asks her to come inside. What waits there is not another joke, but a table already set with hot chocolate and cookies. The memory works because of the details: a chain restaurant, a slammed menu, a car full of tears, and a small prepared scene at home. Hilary lets it stay messy. The excerpt does not turn the story into advice. It keeps the mismatch between intention and impact, romance and embarrassment, tenderness and awful timing. The archive frame matters too. This is a favorite because it catches a relationship at the exact moment when love looks least graceful.

As heard by us

A relationship story that turns an Olive Garden blowup into something unexpectedly warm.

The piece turns a heated Olive Garden dinner into a small domestic story with a clean emotional line. It keeps the joke heavy back and forth between Andrew and his partner front and center, then lands on the crying in the car, the refusal to stop teasing, and the later warmth of…

Read the full review in PlayNext →

Why you'd press play

A punny first date turns a packed-restaurant meltdown into hot chocolate, cookies, and a much softer landing.

Read the full recommendation in PlayNext →
Listen to the show on