15 Of The Weirdest Couplings In Hollywood History

Macauley is so...weird and Mila just seems so...normal. These two started dating in 2001 and stayed together for 8 years! That's long time! We're relieved that Mila is now with her rightful partner, her tv boyfriend from "That 70's Show", Ashton Kutcher and Macauley is...doing his best.

Wait, what?! This paring makes absolutely no sense, especially since the two got together back when Tom was 23 and Cher was 39. It was apparently just a fling, but still...stuff happened. Weird!

The Olsen twins are famous for having...interesting taste in romantic partners. Although they looked good together, they just didn't seem to be from the same planet. Lance is a celebrated athlete, whereas Ashley is an ex-child star turned fashion designer. These two started dating when Ashley was 21 but it ended pretty quickly when Lance realized how weird it was that he was dating a girl 15 years younger than him.

So get this...Woody Allen actually dated Soon-Yi's mother, Mia Farrow back in the 80's and even had a kid with her. After that relationship ended, he ended up getting together with her daughter, Soon-Yi. So he's basically dating his adopted daughter. Weird? Yes.

These Olsen twins are relentless! Mary-Kate Olsen married the French President's brother, Olivier Sarkozy in 2015 and is apparently totally fine with the 17 year age difference? He looks like he could be her grandpa.

She was 19 and he was 36. Huge age difference and Evan even said in an interview that dating him was "a mistake". Whatever that means?

These two met on Chelsea's Late Night show and instantly connected. They dated for a while and even flirt with each other on social media to this day. Oprah also did a "special" on their "odd coupling".

Ok...ok...I get it, they're both funny...they both work in TV...but the age difference (12 years) is just...awkward. They kept their relationship a secret so I think they knew it was kinda weird they were dating.

These two dated for a year and a half back in 2004 before calling it quits. I just can't imagine what they would have talked about?...

These two dated back in 1999 when Kristen (3rd Rock From The Sun) was actually more famous than Ryan! This pairing made sense at the time, but now that he's a famous movie actor...it just doesn't seem right...

What do you get when you put together a world-famous Bollywood star and a Disney channel boy band singer? This strange...relationship. These two tied the knot just last year, oh and Priyanka is a whole 10 years older than Nick. Odd?

Pete Davidson knows he's not exactly...Grade A dating material, so why does he keep ending up with these over-the-top, super hot babes? A few weeks after he broke up with Ariana Grande, he hooked up with Hollywood starlet, Kate Beckinsale. The relationship didn't last and besides...she's a whole 20 years older than him...

If this was high school, these two would be natural enemies. Avril, the rocker chick and Brody, the obnoxious pretty-boy jock. Nothing about these two makes sense, but they actually dated for two whole years before calling it quits.

Ok who has Ryan Reynolds NOT dated? I would never peg famous hollywood leading man to date "alternative guitar girl". These famous Canadians dated for 5 years and were engaged for two of them. Crazy!

Not exactly an obvious match. One of them is a famous Hollywood actress and the other is the lead guitarist of punk rock band "Good Charlotte", but these two are actually kinda cute together. They were actually introduced by Cameron's friend Nicole Ritchie who is dating Benji's brother. They met and hit it off and are now married after knowing each other for 7 months. Wow, that's what I call moving fast!