Before starring as Andrew Clark, the athlete in “The Breakfast Club,” Emilio Estevez was introduced to the stunning Demi Moore (who was still before her “Indecent Proposal” and “Ghost” days). They dated for a while and got engaged but never tied the knot.
They were both madly in love with one another, but apparently, that was not enough for Estevez to not play the game with another woman simultaneously. When Demi’s therapist advised her not to take it any further with Emilio, she knew they had to go separately. But other relationships were not too far ahead for either of them.
Corey Feldman and Drew Barrymore
The child stars of the 1980s were very different than the ones we see today. Back then, if you appeared in one movie, you probably appeared in them all. During his teens, Corey Feldman starred in "Friday the 13th", "Gremlins," "The Goonies," and the all-time classic, "Stand by Me."
In 1989, Feldman dated Drew Barrymore, also known as a child star of those days. It's actually kind of sweet when you think about it — they were probably the only people who could fully understand each other. The two came together as an item to the Oscars that very same year.
Tyra Banks and Seal
In the 1990s, Seal was one of the biggest stars around, with his greatest hit, "Kiss From a Rose," winning several awards at the time. Seal is better known for his relationship with Heidi Klum (which was highly publicized but famously ended in a divorce), but before then, another supermodel was on the scene.
Seal and Tyra Banks dated for three months. Their relationship was kept relatively low-key, and besides one event that they appeared together, no one made a fuss of them. In fact, other than Seal's marriage to Klum, both stars' love life didn't make too many headlines.
Melissa Gilbert and Rob Lowe
Mellisa Gilbert spent most of her childhood years on the little prairie, so no wonder she fell madly in love with mega babe Rob Lowe when she first met him. We doubt it if there were charmers like Lowe on the prairie. Gilbert and Lowe went out for over six years, with a few breakups along the way.
At one stage, they got engaged, but that never led to a wedding. Rob carried on with his life, spreading his charms on other women, and Melissa nourished her career, became a producer and politician, and is happily married to Timothy Busfield.
Gwyneth Paltrow and Ben Affleck
This story has somewhat of a circular structure: Ben Affleck and Gwyneth Paltrow met on the set of one movie and then had to meet again, after they had already broken up, to promote another movie. That, in itself, already sounds like a movie.
They first fell in love in 1998's "Shakespeare in Love," and by the time their 2000 flick "Bounce" came out in the year 2000, they were already apart. Gwyneth was quoted saying that Ben isn't the type of boyfriend you marry, but the one you date to heal childhood trauma. We don't know if that's a compliment or not.