1.Jennifer Aniston and Tate Donovan got engaged in 1998.

They ended things shortly after, but he had already committed to filming his guest role on Friends as Josh-u-ah, so they ended up filming it having literally just broken up.

2.Tate Donovan was also engaged to Sandra Bullock at some point during their relationship that started in 1990.

They ended it all in 1994.

3.Jeffrey Dean Morgan and Mary-Louise Parker got engaged sometime in late 2007-ish.

They split up in April of 2008.

4.Laura Dern was engaged to Billy Bob Thornton during their relationship from 1997-1999.

Their relationship ended when Billy Bob literally just started a relationship with Angelina Jolie and then married her while Laura was away working on a movie!!!! He never even broke up with her!!!!! Absolutely nuts.

5.Laura Dern was also engaged to Jeff Goldblum. They got engaged in 1995.

They ended up breaking up in 1997.

6.Rashida Jones and Mark Ronson were engaged in 2003.

They broke up a year later. ¯\_(ツ)_/¯

7.Rhys Ifans (who now plays Otto Hightower on House of the Dragon) and Sienna Miller were engaged in 2007.

They broke up in 2008.

8.Lea Thompson and Dennis Quaid were engaged in 1984.

They stayed engaged until they broke up in 1987.

9.Julia Roberts and Dylan McDermott were engaged in 1989/1990.

Apparently, she ended their engagement to date Kiefer Sutherland.

10.Which brings me to Julia Roberts and Kiefer Sutherland getting engaged in 1990.

They broke up lit'rally three days before their wedding in June 1991.

11.Minnie Driver and Josh Brolin got engaged in 2001.

They ended their engagement five months later.

12.Chrishell Stause and Matthew Morrison got engaged in 2007.

They ended their engagement later that year.

13.David Moscow and Kerry Washington got engaged in 2004.

The engagement lasted until 2007, and then, they split up.

14.Robin Wright and Ben Foster got engaged in 2014.

They ended up breaking up in 2015.

15.Magician David Copperfield and supermodel Claudia Schiffer were engaged sometime in 2004-ish.

The never got married, and broke up in 1999.

16.Katie Holmes and Chris Klein got engaged in 2003.

They ended the engagement and relationship in 2005. Then came Tom Cruise :).

17.Ben Stiller and Jeanne Tripplehorn got engaged in 1993.

They were engaged until they broke up in 1996.

18.Ryan Reynolds and Alanis Morissette got engaged in 2004.

They ended the engagement and broke up in 2006.

19.Cameron Diaz and Jared Leto allegedly got engaged in 2000.

Their relationship ended in 2003, though, without a wedding.

20.Emilio Estevez and Demi Moore got engaged in 1984.

They broke up in 1987 when Demi indefinitely postponed the wedding because Emilio was caught cheating.

21.Kyle MacLachlan and Linda Evangelista got engaged sometime around 1995.

They never got married, and ended things in 1998.