Glam Rock, Part 3 (Patreon)

And we're on schedule with part 3! At least our most recent schedule, anyway.

So there's kind of a trick with doing spoken romance in a roleplaying game - your players have to be actually slightly decent at it in real life to roleplay it, otherwise it does get to be super awkward. The catch is that once you realize the opposite gender is people too, it's really simple. In this case, one character thinks he's going to get something from a girl, but the girl also thinks she's going to get something she wants out of the character. It's not a passive interaction - flirting is affirmative and proactive in a lot of ways, and any sort of suggestive material is only testing boundaries.

You can gloss over the suggestive stuff. It's safe to assume your friends don't really need to have their boundaries tested. If it's clear where things are going, then you can kind of announce that banging happened, and once you're done with all the dancing around it's just out there in the open as established fact. Your problem will appear if a player doesn't quite get the purpose of the nuance and goes a bit heavy-handed into it, because then they're testing your boundaries through a fictional character, and you'll find yourself in that dilemma where the character has a high charisma on paper whereas the real person is weirding you out.

I haven't done reasonable courting-type roleplay often, but my favorite thing about it is to have the other member realize that they've signed on with some kind of sociopathic murderer who is never going to be able to settle down, and then have the relationship disintegrate into sniping and bickering. You're doing time skips, so it's not too weird, often given the usual circumstances, to go from flirting, to dating, to wanting to kill one another within only a few sessions of a campaign.

To be honest, 90% of the time this sort of improv probably shouldn't be done at all because even if some players can pull it off, you don't necessarily want to encourage the players who can't pull it off to give it a try. That or, you know, instead of roleplaying it you can make it a dice roll with almost no description, and then immediately descend into the bickering lover angle afterward.