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Celebrities Playing Cupid: Matchmaker Stars Who Set Up Their Famous Friends (PHOTOS)

Posted: 04/27/2012 12:08 pm Updated: 04/27/2012 12:08 pm

In addition to possessing wealth, good looks and charm, celebrities have one more advantage when it comes to meeting a significant other -- their celebrity pals.

It turns out there are tons of folks in Hollywood who love playing the role of cupid in their friends' lives. But anyone who has been set up before knows that while friends may have our best interests at heart, it may turn out to be a disaster. As it also turns out -- celebrities are horrible matchmakers.

While there are a few notable exceptions, most of the matches made by a famous friend playing Cupid ended in heartbreak.

We've rounded up all the celebrity couples brought together by friends or co-workers, and we think they should take their track record for successful pairings as a warning, and find their own dates instead.


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  • Busy Phillips

    Busy Philipps is <a href="" target="_hplink">responsible for one of Hollywood's cutest couples</a>. The 32-year-old actress introduced her former "Dawson's Creek" co-star and BFF Michelle Williams to her former "Freaks and Geeks" co-star Jason Segel. The relationship is brand-new, but we have to admit, we are pretty smitten with them -- <a href="" target="_hplink">especially given the adorable photo-booth photos of Michelle that Jason had plastered to his phone</a>. We hope these two can make it in the long run.

  • Anne Hathaway

    Happily married couple Emily Blunt and John Krasinski have Anne Hathaway to thank for introducing them. Anne and Emily became close on the set of "The Devil Wears Prada" and things went well when Anne introduced her to former "The Office" star John Krasinski. "I wasn't really looking for a relationship and I was thinking I'd take my time in L.A. and everything. Then I met (Blunt). I was so nervous (thinking), 'Oh God, I think I'm going to fall in love with her.' As I shook her hand, I went, 'I like you!' So if anybody's looking (into) how to pick up a girl, that's the way you do it!" <a href="" target="_hplink">he told Ellen DeGeneres in 2011. </a> The couple married in Italy in July 2010.

  • Gwyneth Paltrow

    One of the most unlikely couples in Hollywood met through a celebrity pal who played matchmaker. Actress <a href="" target="_hplink">Gwyneth Paltrow set up a dinner for Jake Gyllenhaal and Taylor Swift</a> at her home in London. Gwyneth has known Jake for a long time and her husband, Coldplay singer Chris Martin, has a friendship with Taylor. Given that the odd pairing didn't last very long, Gwyneth might want to hand up her bow and arrow and leave playing Cupid to someone else.

  • Justin Bieber

    Justin Bieber <a href="" target="_hplink">attempted to set up his pal and producer, 17-year-old Julian Swirsky, with reality TV star Kendall Jenner, last summer</a>. The teenage popstar tweeted at Kendall: "Hey Kendall Jenner, you should let my boy [Julian Swirsky] take you out on a date." Kendall was game, but only Justin and his girlfriend Selena Gomez would join them on a double date. Despite Bieber's best efforts the two never became a couple.

  • Bobby Coleman

    Miley Cyrus already had a crush on her "The Last Song" co-star Liam Hemsworth, so she <a href="http://" target="_hplink">enlisted her other co-star, 12-year-old Bobby Coleman, to help woo the Australian actor</a>. "[Bobby] is probably one of the most hysterical kids I've met in my life. This kid will do anything for five bucks. I paid him 10 bucks to go ask Liam if he liked me. I sent him back and forth. It was really funny," Miley told reporters in 2010. Two years later, Miley and Liam are still going strong.

  • Kristin Cavallari

    Kristin Cavallari reportedly <a href="" target="_hplink">played matchmaker</a>, setting up actress Jenny McCarthy with Chicago Bears linebacker Brian Urlacher. The actress is apparently "giddy" about the new romance. We'll see how long this one lasts.

  • Delta Goodrem

    Delta Goodrem <a href="" target="_hplink">reportedly set up Joe Jonas with her TV presenter friend Renee Bargh.</a> The 26-year-old singer, who dated Joe's younger brother Nick until February 2012, played Cupid for the pair after Renee broke up with her boyfriend, Shannon Holtzapffel. The two never admitted they were a couple, but were often spotted getting cozy.

  • Justin Long

    Actor Justin Long <a href="" target="_hplink">really wanted to play matchmaker</a> when he introduced his "He's Just Not That Into You" co-star Ginnifer Goodwin to actor Joey Kern. Long spent weeks trying to hook the two up, and went to great lengths to get them together -- even flying them to Mexico, where Goodwin was working on a film, just to introduce them. "Justin had been trying to figure out how to set us up... Justin really knows us and I really trust him and his judgment,"<a href="" target="_hplink"> Goodwin told reporters. </a> Sadly, all of Long's hard work didn't pay off. The couple became engaged, but they never made it down the aisle, <a href="" target="_hplink">breaking off their engagement in May 2011. </a>

  • Oliver Stone

    Director Oliver Stone encouraged love to bloom between his "Wall Street 2: Money Never Sleeps" leads. <a href=",,20369820,00.html" target="_hplink">Stone told <em>People</em> the relationship between Carey Mulligan and Shia LaBeouf was all thanks to him. </a> "You could see their chemistry right away, and it was pretty powerful," Stone admitted. "They were completely professional on the set, but there was no mistaking what was happening." Despite Stone's efforts to encourage their relationship, it just wasn't meant to be. <a href="" target="_hplink">Carey and Shia called it quits in October 2010.</a>

  • Jordan Farmar

    We wonder if Kris Humphries is still friends with teammate Jordan Farmar, since Farmar introduced him to his soon-to-be ex-wife Kim Kardashian. "I introduced them in New York and they have come a long way since. Not too long, but a lot has happened," <a href="" target="_hplink">the former LA Laker, who now plays alongside Kris on the court, told OK!</a> magazine. "It was kind of mutual thing with them asking about each other." As we all know, it wasn't a match made in heaven. After a 72-day marriage, Kim filed for divorce.

  • Donatella Versace

    This is one relationship that did not end well, but it started thanks to designer Donatella Versace. Halle Berry met Gabriel Aubry while shooting a Versace ad in 2005 and Donatella gave them the push they needed. "Of course, I was at the shoot when they met. I know him very well. I pushed a little bit. I said, 'Why don't you go out together.' I said it in front of them. It went well at the shoot," <a href="" target="_hplink">she told <em>People,</em> adding</a>: "It was a moment when both of them were single. And they are both such nice people." Though the couple had a daughter together in 2008, the relationship didn't last. In 2010 they announced they were separating and have been going through a <a href="" target="_hplink">nasty fight for custody of their 4-year-old daughter. </a>

  • Selena Gomez

    Selena Gomez tried to set her BFF Taylor Swift up with her good friend, Forever The Sickest Kids frontman Jonathan Cook. "Selena suggests girls for me to date," Cook <a href="" target="_hplink">told E! News</a>. "And she told me she has to approve of any girls that I date." The two never dated, but it might have something to do with the fact that Taylor was seeing "Twilight" star Taylor Lautner at the time. Maybe Taylor hadn't told Selena she was dating Lautner, which is understandable, <a href="" target="_hplink">seeing as how Selena dated him first. </a>

  • John Krasinski

    Actor John Krasinski r<a href="" target="_hplink">eportedly played Cupid for his "The Office" co-stars B.J. Novak and Mindy Kaling</a> -- helping to reignite their former romance. Kaling and Novak broke up in 2008, but got back together after some helpful meddling from their co-star. Krasinski reportedly got the two together again under the guise of helping plan his wedding and honeymoon. The time together was well spent and the two picked up <a href="" target="_hplink">where they left off. </a>

  • Jude Law

    Jude Law <a href="" target="_hplink">reportedly played matchmaker for his "Sherlock Holmes" co-star Rachel McAdams, and his friend Josh Lucas. </a> The two started dating in January 2009, but it wasn't the right match for either of them and they decided to call it quits in August that same year.

  • Ellen DeGenerges

    After seeing "50/50", talk-show host Ellen DeGeneres became convinced that the film's leads, Joseph Gordon-Levitt and Anna Kendrick, should be a real-life couple. Although Ellen can be pretty convincing, she wasn't able to make the relationship happen.

  • Jon Stewart

    In March 2011, "The Daily Show" host Jon Stewart played Cupid for a moment when he jokingly tried to set up an audience member with actor Jake Gyllenhaal.

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Filed by Stephanie Marcus  |