1. Calista Flockhart

She Was: 38 He Was: 60 These two started dating in 2002 and got hitched in 2010 and are still making it work.

2. Mary-Kate Olsen

She Was: 29 He Was: 46 Mary-Kate Olsen married Olivier Sarzoky, former French President Nicolas Sarkozy's half-brother, in 2015.

3. Anna Nicole Smith

She Was: 26 He Was: 89 Can you imagine marrying someone 63 years older than you? Well, that's what Anna Nicole Smith did back in 1994

4. Celine Dion

She Was: 26 He Was: 52 The singer had been dating René Angélil for seven years when they got hitched in 1994. They stayed married until his death in January 2016.

5. Phoebe Cates

She Was: 26 He was: 42 Phoebe Cates was just 26 when she married Kevin Kline, after they met at the audition for The Big Chill way back in 1983.

6. Katie Holmes

She Was: 27 He Was: 43 The stars dated for about a year before they got hitched in November 2006 — you know, after Tom jumped all over Oprah's couch.