We all want to win a mate, but the giant cuttlefish’s tendencies go into the contrived-romantic-comedy sphere. Giant Australian cuttlefish (Sepia apama) will normally fight for mating rights but some males, too small to compete normally, win their females by cross-dressing. Disguised as receptive females, they flirt their way into the larger males harem then covertly mate with the girl. The females aren’t put off by it, actually preferring to mate with the smaller males about half of the time.
You can watch a wonderful BBC video of this drag show in action here. Furthermore, Humon, a very talented cartoonist, has a series of comics about other weird animal mating strategies you can see here.
Sources: Hall and Hanlon (2001), photo courtesy of Wikimedia