25. Paris Hilton and Paris Latsis
Couple Nickname: None
Dated Between: 2005
We're pretty convinced that Paris Hilton's ultimate match would be herself, so someone who at least shares her name seems to be a close second. Hilton apparently agreed, at least for a little while, because she was engaged to Greek shipping heir Paris Latsis for five months in 2005 that were highly documented by the paparazzi, before they broke up because Hilton felt she was too young to be getting married.
The only thing lamer than the pathetic length of this relationship was the fact that Latsis was apparently so taken with her that he got her a ring that had a carat for every year of her life at the time, making it 24 carats and worth $4.7 million. It was so big that apparently the poor little rich girl complained that it was too heavy for her to wear, prompting Latsis to respond by buying her a Cartier band to wear instead. Seriously, dude?