Romance in a one shot?

So during my last session, I made up a physical notice board for my players so that they could be more immersed in the experience. To make it more realistic I included some random non-adventurer messages including a post looking for a young woman to accompany a Lord's son to a luncheon.

The players weren't going to follow that through, but one of our players won't be available next week and so they chose that mini-quest to complete and view it as a bit of a humorous enterprise. I picture the experiences a bit like a classic 90s movie. With the characters that are coming, there will probably be some illusory gender-bending and such, meaning that while one character 'dates' the target, the others have to break into the party and help the poor bachelor not make a fool of himself and hide the truth from everyone, bolstering the confidence of Mr Single and getting a quick buck.

Some ideas I had include the poor sod getting into a fistfight over his lady's honour, which he would pitifully lose unless the PCs figured out ways to help out (without murdering people) and various other cliches like fixing his suit when he spills upon himself or what have you.

Has anyone tried anything like this before? Or have even heard about adventures like this? I am perusing the Dungeon Masters Guild and looking for Valentine modules for ideas, but any suggestions for problems/mishaps and running the session?

P.s. This is intended to be a bit of a jokey session if you hadn't realised, feel free to throw wild suggestions.