Celebrities Who Dated


You always remember when two celebrities get married (Even if the marriage only lasts 72 hours), but you don't always notice when they have a casual fling.

There is no doubt that the celebrity world is one of the smallest ones out there. Before Kim and Kanye or Angelina and Brad, did you know that Kim Kardashian dated Mariah Carey’s husband Nick Cannon?

Here's a list of celebrity couples that may surprise you.

Edward Furlong & Paris Hilton 

Paris Hilton and actor Edward Furlong were around 1999-2000, but little has been published about their romance. I would think this is one relationship, she'd rather keep in the closet. Paris is a celeb serial dater. The queen of cavorting boasts an impressive list of conquests (official and rumoured:) Deryck Whibley, Edward Furlong, Rick Salomon, Nick Carter, Joe Francis, Mark Philippoussis, Colin Farrell, Jason Shaw, Simon Rex, Tom Sizemore, Val Kilmer, Leonardo DiCaprio, Andy Roddick, Travis Barker, Chad Michael Murray, Paris Latsis, Stavros Niarchos, Mario Lopez, James Blunt, Jared Leto, Benji Madden, Doug Reinhardt.

Miley Cyrus & Tyler Posey

Teen Wolf star Tyler Posey revealed to Seventeen magazine that Miley Cyrus was his first kiss. “I worked on a TV show called Doc, starring Billy Ray Cyrus, when I was nine-years-old. His daughter, Miley Cyrus, was my first kiss and girlfriend. We dated for two years and broke up when we were 11. I saw her three years later on TV, and freaked out! We're still friends,” he said.

Fergie & Justin Timberlake

Britney Spears is known as Justin Timberlake’s first love, but a 16-year-old JT dated then-23-year-old cougar Fergie in 1996 when she still went by Stacy Ferguson and was one third of girl band Wild Orchid. Justin finally settled down with Jessica Biel, and Fergie has a son with husband Josh Duhamel.

Chelsea Handler & 50 Cent

Funny lady Chelsea Handler and rapper 50 Cent “casually dated” after she interviewed him on E! talk show Chelsea Lately. Handler told Howard Stern he pursued her with over-the-top flower deliveries (50 white roses) and flew to Nashville just to see her again. They were together for a few months..

Jessica Alba & Mark Wahlberg

Jessica Alba and Mark Wahlberg had a short fling in 2003?! According to People, Alba and Wahlberg were spotted getting cozy in Miami Beach on New Year's Eve, and briefly dated. By January 2005, she met her future husband Cash Warren, who was an assistant director on her film Fantastic Four.

Sandra Bullock & Matthew McConaughey 

The pair dated for about a year when they shot A Time to Kill in 1996. “We both have a lot of strong feelings for each other,” Matthew has said. “It wasn't the right time before. I do love her, and will always love her. Absolutely.” Matthew is of course married to Camila Alves now, and raising three kids, while Sandra is raising adopted son Louis on her own.

Sandra Bullock (Again!) & Ryan Gosling

Ryan Gosling is perhaps best known for his relationship with Notebook co-star Rachel McAdams, but before Rachel there was Sandra – a full 16 years his senior! The pair dated for a year until 2002, and Ryan has only fond memories of their time together, counting Sandra as among his two greatest girlfriends.

January Jones & Ashton Kutcher

Back in 1998, the year he landed his role as Michael Kelso in That 70's Show, Ashton Kutcher was dating Mad Men’s January Jones. The pair made it to three years before splitting in 2001.

Drew Barrymore & Ed Westwick

Drew Barrymore was busted in a steamy liplock with Gossip Girl's resident bad boy Ed Westwick, aka Chuck Bass, at a Kings of Leon concert in 2008. But their May-December romance (she was 33 at the time, he was 21) turned out to be more of a fling than a long-term relationship. The two never went public

Hilary Duff & Shia LaBeouf

Are there any actresses in Hollywood Shia hasn’t dated?! The actor once shared a date with Hilary Duff, but it was such a disaster, the pair never arranged to see each other again. Shia called it: “Probably the worst date either of us has ever had.” Can you imagine?

Amanda Bynes & Seth MacFarlane

Before MacFarlane's big-screen superstardom — and before Bynes' big meltdown — the duo briefly dated in 2008 despite their 12-year age difference. I wonder what MacFarlane thinks of his former flame now?

Tony Romo & Jessica Simpson & Carrie Underwood 

Sometimes celebrities go for athletes, sometimes it's even the same one.

Singer Jessica Simpson dated Dallas Cowboys quarterback Tony Romo, much to the dismay of fans. Country singer and American Idol alum Carrie Underwood also dated quarterback Tony Romo.

Contributing Editor, Allie Shain founded Allie is Wired in May of 2006 and joined the Glam Network 2 months later. She is a native born Californian, with 15 years experience in television and radio broadcasting. Along with Allie is Wired, she also publishes The Beauty Stop.