January Jones and Ashton Kutcher were pretty much leveled out when they first met in 1998. They were both in the spring of their careers, still taking any role proposed, and were working their way up the success ladder. They dated for three years and decided to go on their separate ways in 2001.
Jones has remarked on several occasions that Kutcher was not the ideal partner and was not supportive of her career at all. Since then, the couple kept climbing, though separately. Jones went on to star as Betty Draper in “Mad Men” and Ashton went on to marry Mila Kunis.
Dennis Quaid and Lea Thompson
The movie "Jaws- 3" brought us a bit more than scary sharks. In 1996, Lea Thompson and Dennis Quaid (who starred in the movie) were seriously dating, and Dennis even proposed. The two were engaged for almost a year but never took the next step.
A few years later, Thompson started to date Howard Deutch, who she met on the set of "Some Kind of Wonderful" and ended up marrying. It seems that Lea Thompson has a thing for men she meets on sets. Then again, these things are bound to happen when people are literally paid to play each other's love interest.
Gwyneth Paltrow and Brad Pitt
In the 1980s and 1990s, you couldn't get better looking than Brad Pitt and Gwyneth Paltrow. They were the most glamorous couple of that era and were adored by all. They dated for two years, which at the time seemed like a lifetime.
A few years later, Gwyneth Paltrow admitted that their relationship ended because she was in a very unstable time in her life and that she practically messed it up. You never know; Paltrow could have saved us the whole Anniston-Jolie story if she would have stuck around. Though it seems like they both landed on their feet eventually.
Drew Barrymore and Luke Wilson
Many couples start their love story on the sets of a movie, and so did Luke Wilson and Drew Barrymore. "Home Fries" and "Best Man" were where it all began for these two. It must make things so easy when your on-screen partner is your real-life partner.
They started to date in 1997 but only lasted until 1999. Barrymore has said in a number of interviews that Luke Wilson is one of the most important people in her life and that she has been privileged to have known him. We feel he's not the only guy Drew said this about...
Madonna and Sean Penn
Sean Penn and Madonna met in the winter of 1985 and married soon after, in August of the same year. That's a good way to make one year the best in less than six months. "True Blue", one of Madonna's greatest albums, was, in fact, dedicated to Penn.
In January 1989, just before celebrating their fourth anniversary, they decided to call it quits and got divorced. None of them seems to have wallowed in it for too long. They have since moved on, with Sean Penn remarrying twice (one to actress Robin Write and once to actress Leila George) and Madonna remarrying once (to filmmaker Guy Ritchie).