1. Joey Lawrence
The 90s stars dated at the height of their mutual fame.
2. Will Freidle
She guest-starred as a love interest for Will's character on 'Boy Meets World!'
3. Carson Daly
Jennifer reportedly broke up with him via press release, a topic they awkwardly addressed on his show years later.
4. Wilmer Valderrama
I mean, who didn't Wilmer date in the early 2000s?
5. Rich Cronin
The singer from LFO claimed that J.Love cheated on him with the guy in the next slide... guess who!
6. Patrick Wilson
Jen spotted Patrick in a Broadway show and had to have him. We totally get that!
The pair hosted the World Music Awards together in Monaco and had a fling, but what happens in Monaco stays in Monaco, right?
8. John Mayer
It has been widely reported that "Your Body Is a Wonderland" is about Love's famous curves.
9. John Cusack
The duo was rumored to have a fling around 10 years ago.
10. Kip Pardue
Remember Kip from 'Remember the Titans'? Jen remembers him as someone she dated briefly in 2003.
11. Jamie Kennedy
These two seemed really cute together! But the comedian and actress were not meant to be, and split in 2012.
12. Antonio Sabato Jr.
The two beautiful people were hot and heavy for a while there before they settled down with other people.
13. Ross McCall
The pair were engaged, but soon after their split she was back with Jamie Kennedy, prompting Ross to wonder if she had been straying.
14. Brian Hallisay
There's the guy! Her baby daddy is also a costar from Jen's show 'The Client List.'