These two were teenagers when they first hooked up and dated in 1991, and eight years later, he played brother Rob to her Josie Geller in Never Been Kissed. You know who has been kissed? Those fake siblings. Josie Grossie indeed.

Long before Charlie Sheen was WINNING Charlie Sheen, he was engaged to a young Kelly Preston pre-Travolta. Allegedly there was a rumor going around that he accidentally shot her in the arm (sidenote: holy crap I never knew this story!). Charlie tells this story that basically this revolver he used to carry in his pants pocket accidentally went off when she picked up his jeans, and the shrapnel hit her arm, thus causing her to bleed. What. TIGER BLOOD, Y’ALL.

Alyssa and Scott met on the set of their 1993 movie Double Dragon, and they immediately knew they’d get married to each other. Scott literally said “People get all oogily around us.” Gag me with a spoon. But he also said, “You can interview us 25 years from now – and we’ll prove we’re not just another couple who met on a movie set.” Ok guys, 2018 – make sure someone from People contacts them for a follow-up interview.

Heather and James first met while she was studying at UCLA, and then later went on to film the movie Diggstown together, but according to James, they spent “every day together for a year”. But the start to an end was when he basically admitted he was only dating her because she was blonde and had big boobs. What a skeeze. Oh and if you can’t tell from this picture, there is a 23 year age different between them.

I couldn’t exactly find evidence these two dated, but they did attend the 1997 Emmy Awards together, as seen from this pic. They were in Spin City together, but did romance happen offscreen too? We’ll probably never know, y’all.

Jerry spiced up his life with a blonde Ginger, but this romance didn’t last long…

Because he quickly moved on to dating E! News host Giuliana Rancic (nee, DePandi at the time). In fact she was dating Jerry when she first met her hubs Bill Rancic, and Jerry kind of had a weird prophecy about their romance. Bill said, “I was at NBC up fronts promoting The Apprentice. O’Connell was on an NBC show, and he jokingly said, ‘I’d introduce you to my girlfriend but I’m afraid the two of you would run off together.’ ” And they lived happily ever after

First of all, how disturbing is this picture??? Rick wrote his song Cold Blooded about his lady love, but his drug abuse problems were too much for Linda to handle, so she broke it off.

Christina met Brad when she was 16, as they had the same group of friends. This pic was taken when she brought him as her date to the MTV Movie Awards – except she ended up ditching Brad that night to leave with another guy!!! Poor choices.

Keaunu met Sofia when her father, Frances Ford Coppola directed him in the film Dracula. Hm. Good thing he already had the part before they started dating.

No one really knows exactly how long the 80s starlet and 80s rapper dated, but per interviews in which he talked about her, their romance lasted about a year. This couple seems unlikely, but the more I think about it, the more it reminds me of a Claire/Bender relationship a la Breakfast Club. Opposites attract?

Okay, so the woman holding Matt Damon’s hand is Skylar Satenstein, who isn’t a celebrity on her own, but definitely has been linked to some high profile names. Matt and Skylar dated while he was at Harvard, and she was an emergency medical physician. In fact she was the inspiration for Minnie Driver’s character appropriately named Skylar in Good Will Hunting. Skyler went on to date OJ Simpson (totally getting a Nicole Brown Simpson vibe from her, no?) and went on to marry -then divorce Metallica drummer Lars Ulrich.

I guess their relationship was high-profile at the time, but I no idea they were a thing, seeing as how I was like 8 when they dated. They starred in two movies, including the Oscar nominated film, Running On Empty, together, and attend the Academy Awards hand in hand that year. Their relationship ended because she objected his drug use, and he died from an overdose in 1993.

Martha Plimpton got around, huh? This was pre-Elisabeth Moss shitshow, and while I appreciate Fred as a comedian, between these two headstrong ladies, I can’t help but think he’s common denominator in the breakups. But what do I know?

Tracy Chapman and Alice Walker were in a relationship in the mid 1990s. They kept it quiet in the public eye, but apparently it was common knowledge among the people in their circles. In 2006, Alice told The Guardian, “My life is not to be somebody else’s impact – you know what I mean? And it was delicious and lovely and wonderful and I totally enjoyed it and I was completely in love with her but it was not anybody’s business but ours.” I think the most important thing to take out of this is ALICE WALKER IS A LESBIAN??? (I’ve never read her stuff, does she talk about it?? Apologies for my ignorance if this is the case)

I like to think that Heath only ever dated Michelle Williams, so this pairing is odd to me. Heather and Heath dated in 2000 after meeting in a club in Prague (because, Hollywood). He even called her his muse at one point. She was also 10 years his senior, but clearly, age ain’t nothin but a number to Heather, right James Woods?