Like most of us, celebrities have dated a wide variety of people—from the downright random to your favorite Hollywood heartthrobs. And, for those who have been veterans on the A-list scene for quite some time now, the pool of potential suitors isn’t really that big when you factor in the recurring characters you bump shoulders with on the red carpet.
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Still, over time, the memory of these odd celebrity couples have faded. Lucky for you, we’ve done the legwork and dug up 10 surprising celebrity pairs from Hollywood’s yesteryear to fawn (or simply express shock) over. From Ryan Gosling and Sandra Bullock to Rihanna and Shia Labeouf, see them all, ahead.

Before Kim Kardashian became one half of Hollywood's most powerful duos with Kanye West, she tried her shot at love with Nick Cannon. The couple dated in 2006, a year before Kardashian's breakout show, "Keeping Up with he Kardashians," premiered. Though their romance only lasted a few months, the tabloids continue to use it to dig up drama, like that Cannon's ex-wife, Mariah Carey, was jealous of his relationship with Kardashian. Cannon later shut that down, saying that Carey didn't even know who Kardashian was.

While filming their movie, "Journey 2: Mysterious Island," in 2012, Vanessa Hudgens and Josh Hutcherson became more than friends. The romance didn't last long, however, with Hutcherson revealing that the two split amicably and are now pretty good friends.
"We were [dating] at one point, but she broke my heart. No, I'm just kidding, that was a while ago, we're really good friends now," Hutcherson told "Today."

Jenna Dewan and Justin Timberlake are now happily married in their own Hollywood "It" pairs. (Dewan is married to Channing Tatum, while Timberlake is husband to Jessica Biel.) However, before finding their own A-list spouses Dewan and Timberlake tried finding love with each other. The couple briefly dated after Timberlake split with Britney Spears in 2002. In an interview with Andy Cohen, Dewan, who was Timberlake's back-up dancer, admitted that they dated, but it wasn't serious.

Despite their 16-year age difference, Ryan Gosling and Sandra Bullock were unabashed about their romance—as they should be. The couple, who met in 2002 on the set of their film, "Murder by Numbers," dated for a year, until splitting in 2003. Despite their short-lived romance, the couple made quite a splash on the red carpet scene, with their frequent PDA moments.

Before Ryan Reynolds married Blake Lively and Scarlett Johansson, he was engaged to Alanis Morissette. The couple, who met in 2002 at Drew Barrymore's birthday party, got engaged in 2004 and dated for two more years until finally splitting in 2006. The two might seem like an odd couple, but they actually both hail from Vancouver, Canada, where they would travel to on their off-time from Los Angeles.

Before Seal fell for Tyra Banks's fellow Victoria's Secret angel, Heidi Klum, he and the "America's Next Top Model" host had a fling. The couple, who had an 11-year age difference, secretly dated for a year in 1996 and only stepped out as a pair once.

Before marrying Ryan Reynolds and becoming one of the most fan-favorite couples in Hollywood, Blake Lively spent some time with Leonardo DiCaprio. The couple's whirlwind romance, which began after they were spotted together in Cannes in 2011, lasted only a few months, with the couple touring Italy and France together. During that time, Lively said she would send DiCaprio pictures of dolls as a sign of their affection.

More than 20 years ago, in the 1990s, Drew Barrymore and Christian Bale went on one date, and, judging from Bale's recounting of the experience and Barrymore's alleged hosting, it went horribly. "We went to see some bloody awful horror film, and that was the end of it. She never called again," Bale told GQ Australia.

Though Rihanna and Shia Labeouf's romance ended after one date, we can only imagine what could've been. In 2007, the singer hit up the former Disney Channel star via text. The pair went out for a single outing, which resulted in them deciding that their relationship was better as friends.
"It never got beyond one date," Labeouf told MTV News. "The spark wasn't there. We weren't passionate about each other in that way, so we remain friends."

Bradley Cooper and Renee Zellweger split only six years ago, in 2011, yet their romance is largely forgotten from recent memory. The couple, who met in 2006 filming their movie, "Case 39," didn't begin dating until 2009. According to Us Weekly, the actors broke up because of Cooper's time-consuming career.