We think these celeb couples should've walked away after the first date and saved themselves (and the world) some trouble...

Hugh Hefner and Holly, Kendra and Bridget
He’s worth an estimated $82 million, has a mansion in Los Angeles, and turned 83 this year. Okay, so on a good day he looks about 60, thanks to all the plastic surgery - but it’s obvious that the girls aren’t there for his personality and good looks. The swanky lifestyle, clothing allowance, and daily pampering are attractive enough. Still, Hef’s unapologetic superficiality and the gold-digging nature of the girls feel a little squicky to those of us who believe in, you know, love and romance. And isn’t it all just a loose form of polygamy?

Sienna Miller and Balthazar Getty
The world found out about Sienna and Balthazar’s affair when they were photographed making out - topless - while on holiday on the Amalfi Coast in July last year. Here’s the thing: Balthazar was married, and his wife had just given birth to their fourth child. Many felt it was bad form of Sienna to cosy up with a married man, even if he happened to be the great-grandson of one of the richest men in the world—and had a fortune that would make Hef’s look paltry. But their summer fling didn’t make it until winter, and the couple parted ways in November.

Marilyn Manson and Evan Rachel Wood
When Marilyn Manson and Dita Von Teese got married, it was a celebration of wonderful gothic weirdness. They made sense together as a couple… until Marilyn left Dita for the 19-year-old  Evan Rachel Wood. The fact that she was 18 years younger than him didn’t seem to dissuade the couple, and she went on to star in the music video for 'Heart-Shaped Glasses'. But the combination of the gruesome-looking Marilyn and the pristine blonde Evan was just too weird, and many breathed a sigh of relief when the pair split after two years.

Jennifer Aniston and Vince Vaughn
Perhaps it’s here that the myth of ‘desperate Jen’ was born. Yes, Angelina started off the shacking-up-with-your-co-star trend, but it seemed as though Jen missed the memo that you’re meant to get together with someone who is, you know, actually compatible with you. Can anyone spell rebound? The rumours of an engagement had everyone alarmed -especially when Jen was spotted wearing a giant diamond ring - but ultimately turned out to be false. Jen and Vince parted after a year, but are reputedly still good friends.

Natalie Portman and Devendra Banhart
“What is she thinking!?” was on everyone’s mind when the first snaps of Natalie and her Venezualan beau appeared. She’s petite, cute, and chic; he has a wild, untamed beard to his chest and clothing that would make a hobo look stylish. They met on the set of Devendra’s music video - which Natalie starred in - and she even moved to LA in order to continue their relationship. Perhaps their attraction was more about inner beauty than outer, but ultimately they turned out to be equally mismatched inside as they were outside, and they split after six months.

Rebekah White