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.
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.
Lisa Kudrow and Conan O'Brien
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.
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.
Jon Hamm and Jennifer Westfeldt
The love story between Jon Hamm and Jennifer Westfeldt began in the late 1990s and lasted almost two decades. They first met in 1997, way before Westfeldt starred in "Kissing Jessica Stein" and before Hamm found himself on the set of "Mad Men."
Jon was a party animal who enjoys the big and ravishing Hollywood parties, while Jennifer was the stay-at-home kind of girl, so they were destined to eventually go their separate ways. Really, people? You're together from 1997 to 2015 and THIS is the thing that finally comes between you? Anyway, Hamm is now engaged to actress Anna Osceola.