It's fun to see which celebrities have dated!  From the adorable (Matthew and Janet?) to the strange (Paris and Val?), here are 10 surprising pairs you probably never knew hooked up, but they did!


  • Getty Images

    Brooke Shields and Liam Neeson

    80's love connection back before Brooke wed tennis pro Andre Agassi, and Liam became the man who beats up the bad guys on screen.

  • Getty Images

    Avril Lavigne and Wilmer Valderama

    Yep, even Avril fell prey to the womanizing That 70's Star back in the day.  She was on a roster that included Mandy Moore, Lindsay Lohan, and Ashlee Simpson.

  • Getty Images

    Chloe Sevigny and Jason Segel

  • Getty Images

    Kate Moss and Jamie Dornan

    Years before he was cast as the captivating Christian Grey, Jamie Dornan was making bedroom memories with Supermodel Kate Moss.

  • Getty Images

    Elle MacPhearson and Kevin Costner

  • Getty Images

    Katie Couric and Bob Saget

    Saget said it was just one date.  Couric says she thought she and Mr. Tanner had a connection, but he never called again.  He later apologized on her talk show.

  • Getty Images

    Paris Hilton and Val Kilmer

    Ew.  Sad to say this hookup wasn't even that long ago.  They two allegedly met at an awards show after party and were spotted getting hot and heavy.  How does this even happen?

  • Getty Images

    Melissa Joan Hart and Ryan Reynolds

    Way before Alanis, ScarJo, and Blake, Ryan was lip-locking with Mel Jo.  The hottie once guested on Sabrina The Teenage Witch, and the two stars say they wound up making out in a hotel room after filming.

  • Getty Images

    Janet Jackson and Matthew McConaughey

    Janet is notorious for flying her hookups under the radar.  Somehow she slipped a brief romance with Matthew by us.  I feel like they just hung out all day and admired each others abs.

  • Getty Images

    Michelle Trachtenberg and Josh Grobin

    I bet Josh was the president of the Harriet The Spy fan club when he was little.