It is Conan O’Brien who we must thank for turning Lisa Kudrow into Lisa Kudrow (and Phoebe). As it turned out, Kudrow met O’Brien at an improv comedy class, and as soon as she set her eyes on him, she fell madly in love. Honestly, these two make such sense together that we’re surprised we couldn’t guess their history with each other.
The two dated for a while until they realized that a great sense of humor on both sides was not enough to keep the two together. O’Brien was the one who encouraged Kudrow to follow her dream and become an actress. And what a great job he did.
Charlie Sheen and Robin Wright
Notoriously a bad boy, every single relationship that Charlie Sheen has been involved in reached the tabloids and the headlines. Except for one. Not much is known about his short affair with Robin Wright, and we are here to tell you all about it.
Sheen and Write had a sweet teenage romance that went on from 1981 until 1982. Sheen was 16, Write was 15, and they two were both in high school. This obviously explains why the press wasn't in on it when the two were an item. Since then, the two have dated many other Hollywood stars, enough to fill up another list.
Juliette Lewis and Brad Pitt
Before he became an A-lister, before his Hollywood royalty days, and before "Thelma and Louise," Pitt dated his co-star at the time, Juliette Lewis. She starred alongside him in "Too Young to Die?" and they were together for just over four years, despite a significant age difference between them.
In 1993 the couple decided to go their separate ways. They had an innocent love affair that would probably never survived if they would have met at an older age. Lewis married (and divorced) professional skateboarder Steve Berra, and Brad became Brad Pitt and had a lot of women to date.
John Cusack and Janice Dickinson
The romance between John Cusack and Janice Dickinson was intensive and wild. Or, at least, that is what the papers said when they discovered the two were getting romantic with each other. The two were seeing each other a little after Cusack ended his story with Claire Forlani and before he had a short fling with Melissa Gilbert. What a busy guy.
It was reported that the two were caught while playing adult games in an airplane restroom. Hey, when they say "get a room" this isn't the kind of room they mean. Dickinson claimed that Cusack had no sense of humor and that she found him pretty dry.
Jessica Simpson and Jensen Ackles
Jenson Ackles was Jessica Simpson's first love and the first guy to give her a broken heart. In 1998, when Simpson was just 18 years old, she dated the "Supernatural" star, Jensen Ackles. Not long after, their romantic love affair in life would turn into a horror movie, for Simpson at least.
It took Simpson a long time to get over Ackles. The poor thing. On one episode of "Newlyweds," Simpson told her ex-husband Nick Lachey, that she was devastated after the breakup with her first love. She never mentioned the name, but it was obvious who she was referring to.