Hmmm ... OK Professor, a good start, but let's see if we can't refine it a little.
Forget the jewels, order some porn, or perhaps outlandish sex toys - doesn't matter so much, just so long as it is distasteful, and prefferably illegal in Doug's home state. But don't use his credit card, use his girlfriend's card, or better yet, his mother-in-law's card.
Now, that email - don't tell her you want to break it up, tell her you (you being Handruin, of course) love her. You really, really, reallly love her. Tell her that a lot, in nauseating gushing detail. Be sure to include some really bad poetry. That way she will want to break it up - who would go out with the dweeb that wrote that gunk?
Clean out the bank acount. Yup. I mean it's not all that creative but hey - it's money, isn't it?
That fax to the local police department? Tell them about the porn you ordered on his mother-in-law's credit card.
Now we are getting there.