Drew Barrymore has been married, divorced, engaged, and more — with some wildly different experiences.
Famous since childhood, the beloved actress and television host ran afoul of some real creeps but has other exes with whom she remains close.
Though bisexual, Barrymore has only married men. So far, anyway.
Here’s a rundown of her famous relationships, including the marriages that didn’t quite happen or didn’t work out.
At 16, Drew Barrymore had her first engagement
In 1991, Drew Barrymore was briefly engaged to to Leland Hayward III.
She was 16 years old, already famous. He was 25.
We can be thankful, at least, that the engagement did not last.
She also did not marry Jamie Walters
At 17, Barrymore was in a relationship with 23-year-old Jamie Walters.
This romance with the fellow actor lasted from 1992 to 1993.
The two did become engaged. Walters proposed with a diamond ring.
Though they did not end up having their spring 1993 wedding as planned, they did get tattoos of each other’s names.
Drew Barrymore’s first husband was Jeremy Thomas
In early 1994, 19-year-old Drew Barrymore had been dating 31-year-old business owner Jeremy Thomas, who was originally from Wales.
He had been allowing the teen actress to drink at his bar.
After only six weeks of dating, they impulsively married in the wee hours of the morning.
Just 19 days later, they separated. A couple of months after that, Barrymore filed for divorce.
She accused Thomas of marrying her for her money and in the hopes of getting a green card, characterizing him as “the Devil.”
More famously, Drew Barrymore married Tom Green
In 1999, Barrymore began dating Tom Green, a comedic actor.
They became engaged in July of 2000, marrying the following year.
They both starred in Freddy Got Fingered and in the cinematic masterpiece Charlie’s Angels.
In December 2001, Green filed for divorce.
They finalized the split in October 2002. Though at the time Barrymore said that she had stopped “believing in happy endings,” she and Green get along amicably these days.
For about a decade, she dated without marrying
Drew Barrymore had a 5-year relationship with the Strokes dummer Fabrizio Moretti, from 2002 until 2007.
She also dated beloved actor Justin Long, though the two broke up in 2008.
In early 2011, she began to date art consultant Will Kopelman, son of Chanel CEO Arie L. Kopelman.
Drew Barrymore’s third marriage was to Will Kopelman
Later in 2011, Kopelman proposed to Barrymore over the holiday season. The engagement became public knowledge in early 2012.
The two married on June 2, 2012. They welcomed their first child, Olive, later that year. In 2014, the couple welcomed Frankie, their second child.
In 2016, the two separated and divorced — finalizing the split in the space of just a few months.
Even so, it seems to have been amicable, with Barrymore even choosing a home close to her ex to make things easier on their shared children.
We are always, always rooting for Drew Barrymore.