Awkward Celebrity Dating Moments

Even stars have relationship drama they'd rather forget.

That Awkward Moment - We've heard time and again that Hollywood is a lot like high school, which means celebs' dating mistakes and mishaps tend to follow them for years. Inspired by one of our favorite recent comedies, That Awkward Moment — which drops on DVD May 13 — we look back at some of the most awkward celebrity dating moments.

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That Awkward Moment - We've heard time and again that Hollywood is a lot like high school, which means celebs' dating mistakes and mishaps tend to follow them for years. Inspired by one of our favorite recent comedies, That Awkward Moment — which drops on DVD May 13 — we look back at some of the most awkward celebrity dating moments.

Drake and Rihanna - As if the Rihanna-Chris Brown-Karrueche Tran love triangle wasn't awkward enough, RiRi threw another log in the fire when she rekindled her romance with rumored ex-fling Drake. The pair have been seen coupled up all over Europe and courtside at NBA games while poor Breezy sits in jail. He's at a safe distance now, but hopefully Brown's anger management lessons will come in handy when he's sprung and faces the awkward run-in with his ex and her new man.(Photo: London Entertainment / Splash News)

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Drake and Rihanna - As if the Rihanna-Chris Brown-Karrueche Tran love triangle wasn't awkward enough, RiRi threw another log in the fire when she rekindled her romance with rumored ex-fling Drake. The pair have been seen coupled up all over Europe and courtside at NBA games while poor Breezy sits in jail. He's at a safe distance now, but hopefully Brown's anger management lessons will come in handy when he's sprung and faces the awkward run-in with his ex and her new man.(Photo: London Entertainment / Splash News)

Kevin Durant and LeToya Luckett - He's the biggest catch in the NBA, whether you're a team manager or a wannabe basketball wife, and it's only a matter of time before someone snatches him up. Could that lucky girl be former Destiny's Child member Luckett? The pair were spotted on what looked suspiciously like a first date in Las Vegas this week, having us believe Durant's gonna be working on his game during the off season.  (Photos from left: David Becker/Getty Images, A Turner Archives/PictureGroup)

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LeToya Luckett and Kevin Durant - The former Destiny's Child member and NBA star sparked romance rumors last year when an adorkable picture of them on a first date leaked online. Unfortunately, there didn't seem to be a second date in the cards. Durant got engaged to Minnesota Lynx player Monica Wright shortly thereafter. As for LeToya, she gave us a coy laugh when we asked her about the date. "One minute we're eating noodles, and the next I had everybody I knew blowing up my phone," she said good-naturedly. (Photos from left: David Becker/Getty Images, A Turner Archives/Getty Images)

Reggie Bush and Lilit Avagyan - We guess he has a type! The NFL player had us doing a double take when he stepped out with his new woman a few months after breaking up with Kim Kardashian. Avagyan, a model, is the spitting image of Bush's famous former lover. What's more, Avagyan and Kardashian were even pregnant around the same time. (Photo: Alberto E. Rodriguez/Getty Images for ESPY)

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Reggie Bush and Lilit Avagyan - We guess he has a type! The NFL player had us doing a double take when he stepped out with his new woman a few months after breaking up with Kim Kardashian. Avagyan, a model, is the spitting image of Bush's famous former lover. What's more, Avagyan and Kardashian were even pregnant around the same time. (Photo: Alberto E. Rodriguez/Getty Images for ESPY)

Justin Timberlake and Fergie - It's no secret Timberlake has a thing for older women, but his romance with Black Eyed Peas singer Fergie was more Mrs. Robinson than Cougartown. Timberlake dated Fergie back in the 1990s, when she was 23 years old and he was just 16.  (Photo: Frank Micelotta/Getty Images)

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Justin Timberlake and Fergie - It's no secret Timberlake has a thing for older women, but his romance with Black Eyed Peas singer Fergie was more Mrs. Robinson than Cougartown. Timberlake dated Fergie back in the 1990s, when she was 23 years old and he was just 16.  (Photo: Frank Micelotta/Getty Images)

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Chris Brown/Karrueche Tran/Rihanna ("LoveHate Thing," Wale feat. Sam Dew) - "Hold me tight, let me go/ Heal my heart, hurt my soul..." It's an ongoing LoveHate thing with this trio, and 2013 was no different.(Photos from left: Allison Joyce/Getty Images, Steve Mack/FilmMagic, FameFlynet, Inc)

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Rihanna and Chris Brown and Karrueche Tran - The most awkward love triangle in recent memory kept the tabloids fed for weeks on end. Chris Brown couldn't seem to make up his mind between his ex, Rihanna, and his ride-or-die chick, Karrueche. To make this particularly awkward, he confessed his indecision in a series of videos, which he posted to social media. Breezy did everything but take a poll of his fans to decide which chick to call his girl. (Photos from left: Allison Joyce/Getty Images, Steve Mack/FilmMagic, FameFlynet, Inc)

Ray J and Kimye - Kim Kardashian has come a long way since that infamous sex tape, but it seems her co-star Ray J just can't resist bringing up the past. Even though his ex is clearly happy with her new man Kanye, the R&B singer felt the need to mark his terrority last year with the single "I Hit It First." Keep it classy, Ray J.(Photos from left: Mark Davis/Getty Images for BET, Michael Buckner/WireImage)

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Ray J and Kimye - Kim Kardashian has come a long way since that infamous sex tape, but it seems her co-star Ray J just can't resist bringing up the past. Even though his ex is clearly happy with her new man Kanye, the R&B singer felt the need to mark his terrority last year with the single "I Hit It First." Keep it classy, Ray J.(Photos from left: Mark Davis/Getty Images for BET, Michael Buckner/WireImage)

AP.9 and Coco Austin - We're sure Ice T loves Coco, but he probably didn't like her very much when pictures of the model looking more-than-just-friendly with rapper AP.9 leaked online. While the couple's marriage survived the alleged cheating scandal, we're not sure their reality show will.(Photos from left: Mindy Small/FilmMagic, David Becker/Getty Images)

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AP.9 and Coco Austin - We're sure Ice T loves Coco, but he probably didn't like her very much when pictures of the model looking more-than-just-friendly with rapper AP.9 leaked online. While the couple's marriage survived the alleged cheating scandal, we're not sure their reality show will.(Photos from left: Mindy Small/FilmMagic, David Becker/Getty Images)

Khloe Kardashian and Lamar Odom - The demise of Khloe and Lamar's marriage was more tragic than awkward, but things definitely got weird when Odom, who's reported drug addiction and infidelities lead to the end of his marriage, did an impromptu freestyle on TMZ copping to cheating — all while he was actively trying to win back his wife. Wrong move, player.(Photo: Lawrence Schwartzwald / Splash News)

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Khloe Kardashian and Lamar Odom - The demise of Khloe and Lamar's marriage was more tragic than awkward, but things definitely got weird when Odom, who's reported drug addiction and infidelities lead to the end of his marriage, did an impromptu freestyle on TMZ copping to cheating — all while he was actively trying to win back his wife. Wrong move, player.(Photo: Lawrence Schwartzwald / Splash News)

DJ Khaled and Nicki Minaj - DJ Khaled apparently has been holding a candle for his pal and collaborator Nicki Minaj for some time, but rather than confess his feelings in private, Khaled decided to propose to her on live television last year. Nicki's response? Total silence. How's that for awkward!(Photos from left: John Ricard / BET, Kevin Mazur/Getty Images for BET)

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DJ Khaled and Nicki Minaj - DJ Khaled apparently has been holding a candle for his pal and collaborator Nicki Minaj for some time, but rather than confess his feelings in private, Khaled decided to propose to her on live television last year. Nicki's response? Total silence. How's that for awkward!(Photos from left: John Ricard / BET, Kevin Mazur/Getty Images for BET)

Photo By John Ricard / BET, Kevin Mazur/Getty Images for BET

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Shemar Moore and Toni Braxton - Didn't anyone teach Shemar Moore not to kiss and tell? The hunky actor pissed off his ex Toni Braxton when he told us the "Unbreak My Heart" singer was a "wild ride" and a fun fling, but that his first true love was Halle Berry. (Photos from left: Frederick M. Brown/Getty Images, Jennifer Graylock/Getty Images)

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Shemar Moore and Toni Braxton - Didn't anyone teach Shemar Moore not to kiss and tell? The hunky actor pissed off his ex Toni Braxton when he told us the "Unbreak My Heart" singer was a "wild ride" and a fun fling, but that his first true love was Halle Berry. (Photos from left: Frederick M. Brown/Getty Images, Jennifer Graylock/Getty Images)

Ben Affleck - Back when she was dating the actor, Jennifer Lopez featured Ben Affleck in the video for her single "Jenny From the Block." (Photo: Courtesy of Sony BMG Music)

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Jennifer Lopez and Ben Affleck - We're sure putting her boyfriend in her music video seemed like a good idea to J. Lo at the time, but now that the couple has imploded, the "Jenny From the Block" clip is just a constant reminder of a relationship they'd likey both rather forget. We're sure the married father of three will have a good time trying to explain the sexy video to his kids one day.(Photo: Courtesy of Sony BMG Music)

Amber Rose and Kimye and Reggie Bush - There's nothing like getting dumped to bring out the revenge-seeker in a person. Amber Rose refused to go away quietly after Kanye West left her for Kim Kardashian, instead of speaking publicly about her belief that both Kim and Kanye had been cheating on their respective significant others with each other. Sorry, Reggie Bush.  (Photos from left: Eugene Gologursky/Getty Images for DuJour Magazine, CPA/ PacificCoastNews.com, Jesse Grant/Getty Images For Professional Bowlers Association)

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Amber Rose and Kimye and Reggie Bush - There's nothing like getting dumped to bring out the revenge-seeker in a person. Amber Rose refused to go away quietly after Kanye West left her for Kim Kardashian, instead of speaking publicly about her belief that both Kim and Kanye had been cheating on their respective significant others with each other. Sorry, Reggie Bush. (Photos from left: Eugene Gologursky/Getty Images for DuJour Magazine, CPA/ PacificCoastNews.com, Jesse Grant/Getty Images For Professional Bowlers Association)

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Kim Kardashian and Kris Humphries - Kim's short-lived nuptials to NBA player Kris Humphries was embarassing enough without the fact that their entire relationship was documented for reality television. The re-runs of Kim's Dream Wedding were still running when the reality star filed for divorce. (Photo: Fame Pictures, Inc)

Photo By Photo: Fame Pictures

Big Sean and Naya Rivera - The Glee star gushed about her fiancè and planning their wedding in the February issue of Cosmopolitan, but by the time the issue hit the stands, Sean had announced the wedding was off. To make things even more awkward, the seemingly-amicable split quickly got ugly after Rivera accused her ex of stealing a watch on his way out of her house.   (Photo: Jason Merritt/Getty Images for Dell)

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Big Sean and Naya Rivera - The Glee star gushed about her fiancè and planning their wedding in the February issue of Cosmopolitan, but by the time the issue hit the stands, Sean had announced the wedding was off. To make things even more awkward, the seemingly-amicable split quickly got ugly after Rivera accused her ex of stealing a watch on his way out of her house.   (Photo: Jason Merritt/Getty Images for Dell)

Photo By Photo: Jason Merritt/Getty Images for Dell