Tom Cruise, Age 57 – Single

Tom Cruise has certainly been part of many high-profile relationships, but what’s even more surprising is that during his 80s phase of being attracted to older women, he even dated Cher! They reportedly met at Madonna’s wedding in 1985, but clearly didn’t last that long. They do remain friends, however.

Probably his more public relationship was the one with Katie Holmes, especially after his public declaration of love in 2005. They got married, had a child together, only to split up in 2012. Tom is now revisiting his 80s days, getting ready for 2020’s Top Gun: Maverick.