My dad did something like this once.
I had gone on a date with this girl, talking about our shared interests, her new job at a food place, and how I'd be graduating college soon, moving to the city & starting a job I had lined up. Things were going really well until my friend walked up.
Relevant context: I had been in some legal trouble years before, and was waiting to hear a response of my petition to the court to clear my record.
My friend asked if I had any updates on the "court thing", which I responded to with something along the lines of "still waiting".
Now this topic was something I would usually bring up pretty early just because I'm an open book, have straightened out, and know folks generally would rather know some things early on. But I like to control the delivery and my friend kind of blew that chance up.
She asked for more details, which I gave the same way I usually would, but the damage was done. Noticing the date going stale, I wrapped things up before it got worse. I attempted to set up a 2nd date with a couple calls & messages, but that went nowhere.
Oh well, you win some you lose some. Still, my dad's my best friend so he heard about it.
A month or two goes by, and I had moved into the city, bought my uncle's old BMW, got a nice but noisy apartment, and was barely scraping by at the bottom of the corporate food chain before returning home to visit my parents.
Cue the Dad move: He wants to go to lunch one day I'm back and recommends McCallister's, the place she got her new job at.
"Nah dad, that girl I liked started working there and with our luck we'd bump into her- let's avoid any awkward scenarios & go anywhere else."
"No- I'm craving McCallister's"
Whatever- I drive him over, we go in, and sure enough- she's the only one working a register. When we get up there, she recognizes me, and we awkwardly say hello before she asks if I got the job & how it's treating me.
Me: "It's going alright, I-"
Dad: "Alright? ALRIGHT?! - SON- quit being modest. I'm so proud of him, he's got this beautiful apartment in the middle of the city, he's driving that BMW outside, and making BANK right out of school. You know what? You're buying lunch today- NOT LIKE YOU CAN'T AFFORD IT!" (something along these lines)
She seems impressed & asks if I'd like to catch up while I'm in town to which I politely declined. But man, dad sure had my back and earned his free lunch that day haha. Put a shit eating grin on both of our faces with that move