Examining Ex Etiquette

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I have run into a predicament that I would like to throw out to all you insightful ToastedRav site-surfers. This is not "my friend" or "someone I talked to." This is an actual situation that I have run into with an ex, and I'm owning up to it:

A couple of years ago, I was dating a real loser that I will call "Imbecile Idiot Cheapskate." He's long gone, and I've been dating my amazing and handsome current beau for over a year, but I have one lasting problem with my ex: he owes me money. It's not thousands of dollars, but it's more than a few tanks of gas. When I lent it to him at the time, it was with the understanding that he would pay me right back. But when we went our separate ways, I still had a big hole in my wallet. I want him to pay me back, and have suggested that he pay up or else. He says "sure," then never actually does.

That sounded a whole lot like an episode of Maury, but bear with me. My question is this; should I take more drastic measures to make Imbecile Idiot Cheapskate pay me back, or should I chalk it up to a lesson learned about why not to let friends borrow money? Friends have suggested that I take legal action, but I'm not exactly a sue-happy type of girl.

And what exactly are the etiquette rules that one is supposed to follow in regards to exes? Hopefully you each return personal items to your ex-significant other, but what about gifts? Does it matter how recent the gift was, or should you just keep it no matter what?

This may or may not be my ex on the left. Don't judge me.