Couple Nickname: None
Dated Between: 1991 - 1995

Everyone knew that 26-year-old Anna Nicole Smith's relationship with 89-year-old J. Howard Smith was a sham from the beginning, probably even J. Howard Smith himself.

While part of us sort of understands his wishes to have one last hurrah before death, like a sort of bucket list thing, it's also hard to look past the whole 63-year age difference thing, as well as the fact that Smith's only intention in marrying Marshall was to get in on the gigantic fortune he was going to leave behind upon his death. We ain't sayin' she a golddigger but—well, that's exactly what we're saying.