Yes. It would have to be for an event I would be embarrassed to show up for alone. But we’d end up getting along and falling in love in a single day, but there’d be some kind of fight or misunderstanding. “(S)he doesn’t love me, I was mistaken, and it was just a business transaction”
Then one of us would realize our mistake (hopefully at a bus or train station, or in a moving car) and race to confess our love to the other.

I doubt I have enough money

Prefer to choose them myself I think ..

No.

I want to say no, but I’m sure there’s some social situation where it would be gratifying to be petty and show up with someone awesome and I’d consider it lol

Maybe, if it included a car.

Nope

like pimpin?