I've always enjoyed Jacob Hunt's My Doomed Affair, a silly and very well-drawn comic strip that used to appear in the pages of Athens' weekly newspaper Flagpole. It has just enough of a mean-spirited edge to keep readers from really sympathizing with the comic version of Jacob. He's immature and thoughtless and really funny.
In the comic, which usually appeared weekly, Jacob is dating a girl named Apryl. They really don't treat each other badly; it's just that he's so much less serious about anything than she is, and she doesn't react very well at all to his teasing. Plus, she puts her feet on his car's dashboard. They clash about anything, in zings timed perfectly well for four-panel strips.
Hunt submitted four strips, reworked into a wider "Sunday" format, to syndicates without success. These are included along with a selection of the "dailies" in the second of two 32-page minicomics. I picked up my copy from Bizarro Wuxtry. You may drop that store a line by following the link above; the comics don't appear to be sold on Hunt's website. He also seems to have ended the strip, which is a shame, as it was always a highlight of Flagpole's funny page.
I love his expressive art and the characters' great big eyes, but this really was not the sort of format that could really go on forever. Even the strip's title dooms it, you know? Reading the paper on a monthly or sixth-weekly trip to Athens, even I was surprised, a couple of years into its run, that Apryl had not dumped him yet. Happily recommended.