of course, this immediately lends to a set-up where she tries to kiss him and he desperately attempts to avoid it.

You saw that one a mile away, didn't you?

Who wouldn't. After all, she threaten him if his lips wander towards hers. But, all this might end up doing is for her to ask him why he doesn't want to kiss her. Oh boy, talking about plans going wrong.

Its a classic set-up!

Easy solution: "Hey, you said I couldn't kiss her. You said nothing about keeping her from kissing me."

true enough- but would you manage to get that out before Giddy breaks a limb?

What romance is complete without the threat of violence?

He is going to get messed up either way :D

Don, kiss Lilac anyway. Then turn around and pay off the debt as though you lost, take the beating from Giddy and, finally, tell Lilac the truth... after you've asked her out again. I've got a feeling that the luscious little halfling will be worth every bit of it.

(I also have a suspicion deep in the back of my head that Lilac already knows about the bet, and is using it to get what she wants.)

Every cute girl has an overprotective friend (or father or brother), that's just something a guy has to deal with.

Don is rich? I'm missing out on a lot of the context here...

There is a bit of a back story with Don I haven't yet used.

Don isn't actually rich though most of them think otherwise because he has his own place and seems to get his money from somewhere. In fact its a trust that just cares for his general expenses and in an outline for another story I have a rough outline for somewhere he gets a part-time job in order to afford some wheels. Unfortunately his boss is in direct competition across the streat with the Tunnely family business: "the Happy Halfling Coffee Co." I'm thinking of dusting that story off to follow this one.

As for Don's background, he's from off-world originally (from the Homeworld it's assumed) but doesn't talk about it other than he misses his folks and old friends. A few think that there is some sort of scandal that got him sent to a distant colony world (Farawrath, though the third largest colony world, is on the frontier of UIC space, about 26 light years from Mhar).

I might one day get around to doing a proper comic/manga about Don and the various characters that make the world of the Adamoria Girls, which would likely be a cross between Archie and Please Teacher with a little Excel Saga with a bit of thrown in for good measure.