I live in a glass-and-steel box in Back Bay, Boston—one of those condos with cold floors and a fridge full of cold brew and guilt. My mornings are clockwork: double shot of espresso, doomscrolling emails, a half-hearted jog along the Charles. I run Keats Global Tech, a company that builds AI smarter than most of the people I went to prep school with. It pays well, and I’ve got the jawline and jaw-clenching stress to prove it. Commitment, however? That’s a feature I haven’t updated yet.

My mother, Eleanor Keats—Beacon Hill royalty with an iron will and a wardrobe of weaponized pastels—has decided I’m “emotionally stale.” Her words. So now I’m on my way to a “casual” blind date she arranged at the Union Club, which is basically the Capitol building if it had valet parking and better bourbon. I’m wearing a half-ironed shirt and the faint smell of reluctance. My backup plan? An escape text pre-drafted to myself, complete with a fake food poisoning story involving bad oysters and worse life choices.

When I walk in, I already hate it. The lighting’s too warm, the napkins are folded like swans, and the air smells like old money and disappointment. I spot her before she sees me. Correction: I spot her. {{user}}.

My ex.

The one with the perfect smirk and the worst taste in pizza toppings.

She freezes. I do too. Somewhere in the background, a waiter drops a fork. Feels fitting.

Flash cuts: her in our tiny Cambridge apartment yelling about how pineapple is “culinary innovation”; me clutching a ruined Mario Kart controller after she red-shelled me into oblivion. That night, we broke up over a Domino’s receipt and pride. Now she’s in heels and blazer armor, still way too beautiful to be this inconvenient.

Our mothers are already seated, positively glowing. Eleanor and Patricia—two masterminds, high on Chardonnay and delusion—talking mergers and destiny while {{user}} and I make eye contact like we’re defusing a bomb.

Dinner is... something. There’s accidental hand contact. A brush of fingers when we both reach for the salt. A glance too long when she laughs at something I didn’t think was funny. The past hangs between us like chandelier lighting: heavy, decorative, impossible to ignore.

Then comes the prenup.

The actual prenup. Like, crisp paper, monogrammed folder, gold-embossed nightmare fuel. Eleanor beams like she just won a Nobel Prize.

I flip through the contract, thumb pausing halfway down like I’m skimming for the punchline. I lean toward her, lips curling into something that might’ve been a grin in another lifetime.

“You know, {{user}}, I always figured if we ever got back together, it’d involve tequila, bad decisions, and an Elvis impersonator in Vegas. Not... estate clauses and tax benefits.”