I Negotiated My
Anniversary Dinner
With AI

Here’s a pattern I know a little too well: I go into a celebration dinner with good intentions, and I leave it too stuffed to enjoy the rest of the night. Not because the food was bad. Because nobody was managing the order. Everything sounds good, so everything gets ordered, and by the time the check comes I’ve eaten like I’m training for a competition I didn’t enter.

This year I wanted our anniversary at Ciccio Mio to be different, but not in the boring, “just get the salad” way. I still wanted the good stuff. I just didn’t want to negotiate it with myself at the table, three drinks in, while a bread basket stared at me. So a few nights before, I opened ChatGPT and treated the menu like a contract I needed to review before signing.

I should be honest about who was actually running the show here, because it wasn’t me and it wasn’t ChatGPT. It was my wife, who picked Ciccio Mio and pre-approved the lasagna and the toasted almond gelato as non-negotiable: not up for discussion, not subject to committee, not something I get to “optimize.” She handed me the rest of the menu to go argue with an AI about. Twenty-seven years of marriage will teach you exactly which two dishes matter to her and which ones I’m free to negotiate. She is, by her own description, Ms. Go With the Flow, which I’ve come to understand means she is completely fine letting me run three rounds of calorie negotiations over an appetizer, as long as nobody touches the lasagna.

My first prompt was blunt: review the menu, I’ll tell you what we’re ordering, you tell me the damage. We were splitting everything: focaccia, meatballs, house salad, lasagna bolognese, the toasted almond gelato, an Old Fashioned, and an Amaretto Sour for my wife. I told it to assume I’d eat about 65% of the meatballs and lasagna, and split the rest evenly.

Looking at the breakdown, the focaccia bugged me: 350 calories on bread I’d eat mindlessly before the food I actually cared about even arrived. So I asked for a trade. Drop the focaccia, add either another entrée or appetizer, and tell me if that’s actually smart.

I did not take any of it. I nodded along, then asked to add the Chicken Parmesan instead, its explicitly least-recommended move, because it’s one of Ciccio Mio’s signature dishes and good advice has never once stood between me and chicken parm.

Ignoring three sensible suggestions for “half a chicken parm,” apparently a substantial half, took us from 2,590 to 2,940. With AI’s help, and against its advice, I’d made the dinner bigger, not smaller.

Sitting with 2,940 calories and a month of hard-won 700-to-1,000-calorie deficits, the math finally won the argument the advice hadn’t. We didn’t want to under-eat on our anniversary. But we didn’t want to overdo it either. So we went back through it one more time and made the actual final call: keep the lasagna, because it’s the reason people go to Ciccio Mio in the first place, and let the Chicken Parmesan go. It’s a great dish, and also a dish I can order at a dozen other restaurants on a random Tuesday. And the focaccia, the very thing this whole negotiation started over, quietly talked its way back onto the order. Turns out it’s hard to stay mad at warm bread.

The point of any of this was never to eat less on our anniversary. It was to stop the specific thing I always do, which is order like every dish is my last meal on Earth and then spend the rest of the night doing that slow, seated recovery where you insist you’re “just going to sit for a minute.” I wanted to celebrate: actual celebrating, bread and cocktails and dessert, and then get up from the table the same way I sat down at it.

What the negotiation actually gave me wasn’t a lower number. It was a decision made three days early, by one reasonably calm person and a robot, instead of one hungry guy staring at a bread basket.

We had bread. We had two apps’ worth of splitting. We had the signature pasta, a proper dessert, and a drink each. And when the check came, I stood up from the table like a person who had eaten a nice dinner, not a person who needed a moment.

My wife, who sat through zero rounds of this negotiation and simply ate her pre-approved lasagna and gelato in peace, thinks the whole exercise is quite ridiculous and also thinks it’s exactly the kind of thing that’s kept us married 27 years: she picks the restaurant and the two dishes that actually matter, I go argue with a chatbot about the rest, and everybody eats well. Ms. Go With the Flow, indeed.