Like many child stars (and adult ones), Corey Haim had substance dependency issues during the 1980s’. He was a teen idol and dated some young ladies during those days, with Alyssa Milano being the most famous of them all.
She was a huge star at the time, with “Who’s the Boss?” and would go on to be an even bigger star with roles in hit shows like “Charmed” and “Mistresses”. They dated for a few years and broke up at the beginning of the 1990s’. He must have left his mark on Alyssa’s life, as she was devastated when she learned about Corey’s passing in 2010.
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.
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.
John Cusack and Jami Gertz
Back in the 1980s and 1990s, John Cusack set the standards for all men in the industry. Apparently, not only was he an inspiration for other men, but he was also very popular amongst women. Take Jami Gertz, for example. Gertz was a member of the famously known "Brat Pack" of the 1980s, and the two had things going around 1983.
They met on the set of "Sixteen Candles," and before it even began, the romance was already over. Cusack has since moved on to other relationships, though he has been extremely private about all of them, and Gertz went on to marry philanthropist Tony Ressler.
Jay Leno and Sharon Osbourne
Wait, what? Hasn't Sharon Osbourne been married to Ozzy since the dawn of time? Well, apparently she hasn't. Just like anyone else, she has her own history, though hers is arguably cooler than most. Before Sharon Osbourne was titled the First Lady of Rock&Roll, she had a short affair with Jay Leno.
Yes, THE Jay Leno. They met by coincidence at a bar and had a little fling. As it turns out, Osbourne didn't take the whole thing too seriously. Two months after they had their fling, Leno introduced his now-wife, the love of his life, to Osbourne, making the whole fling — history.