If you have a game where players hailing a cab multiple times a game has some kind of meaningful impact on the direction of play (the way reading a sitch is used multiple times a game and has meaningful impact) then yes there should be a mechanical interface for that (whether its a roll, or a currency spend, et.al.)

A comedy of errors rom-com might call for just such a roll.

A feature of good play testing is discovering what activities players are engaging in the most that are insufficiently supported by the design and then supporting them.