Lindsay Lohan reportedly included James Franco on a list of her romantic conquests, but Franco was quick to shut that down. He denied that anything ever happened between them, which is essentially a public rejection after the fact. Our next entry also shows that Franco's romantic life in Hollywood seems like a bit of a rollercoaster. | © Jimmy Kimmel Live / YouTube
James Franco met Kristen Stewart at the 2012 Toronto Film Festival and liked her enough to ask her out. She turned him down, and then he tried again, only to get rejected a second time. Most people take the hint after the first no, but Franco apparently needed a little extra convincing. | © Pan-Européenne
Jake Gyllenhaal asked Minka Kelly out to dinner, and she said no, simple as that. There's no dramatic backstory or public confession, just a straightforward rejection that apparently stuck out enough to make headlines. Sometimes, even A-listers don't get a second look. | © The Weinstein Company
Harry Styles once showed up at Lindsay Lohan's hotel room door, sent by mutual friends, and she had absolutely no idea who he was. She acknowledged he was good-looking but was already in bed and had zero interest in entertaining a stranger, so she sent him on his way. Styles got turned down not because of who he was, but because Lohan simply didn't recognise him, which might actually be the most humbling rejection on this list. | © Harry Styles / YouTube
Aaron Carter and Hilary Duff dated briefly in the early 2000s, but when Carter publicly admitted he still had feelings for her over a decade later, she was clearly caught off guard. Duff didn't hide her discomfort, pointing out that they hadn't even seen each other in years. Revisiting a middle school romance is awkward enough without the other person bringing it up in public. | © UMPG Publishing
George Clooney reportedly took a shot at Eva Longoria while he was still in a relationship with Stacy Keibler, not exactly the smoothest move. Longoria wasn't interested, and the fact that he had a girlfriend made the decision pretty easy for her. Even Clooney's charm has its limits when you lead with bad timing. | © Paramount Pictures
Emma Watson developed a crush on her Harry Potter co-star Tom Felton when she was just 10 years old, and he was well aware of it. Rather than playing it cool, Felton would openly tell people he saw her as a younger sister, which, at that age, is a pretty brutal thing to hear. Watson has admitted it still stings a little, and honestly, that's hard not to relate to. | © Jay Shetty Podcast / YouTube
Drake has been pretty open about the fact that he fell for Nicki Minaj the moment he laid eyes on her. The feeling, unfortunately, was never mutual, she always saw him more like a little brother than a romantic prospect. Being friendzoned is one thing, but being sibling-zoned by your crush is a whole different kind of sting. | © Drake / YouTube
Shawn Mendes managed to get Billie Eilish's number, which sounds like a win, until you find out she never actually texted him back. He joked about it publicly in 2019, admitting he was still waiting for a reply. Getting left on read is rough enough, but when you bring it up in an interview, it's a whole other level of awkward. | © Shawn Mendes / YouTube
Justin Bieber shot his shot with Rihanna back in 2015, and she was not impressed. He asked for her number and got turned down with one of the most straightforward rejections possible, she told him he was simply too young. Bieber admitted it himself later, which at least shows he could take the hit with some humor. | © Apple TV / YouTube
At a 2013 Cannes Film Festival after-party, Leonardo DiCaprio set his sights on Cara Delevingne, and she wasn't interested. It's not exactly the outcome most people would predict when DiCaprio turns on the charm, but Delevingne shut it down. Even Hollywood's most notorious leading man strikes out sometimes. | © Warner Bros. Pictures
Rumer Willis was just a typical teenager with a celebrity crush: her poster of choice happened to be Ashton Kutcher. Things got complicated pretty fast when Kutcher started dating her mom, Demi Moore. The guy on her bedroom wall suddenly became her stepdad, which is about as awkward as it gets. | © AP / YouTube
Chris Rock once tried his luck with Rihanna, and let's just say it did not go the way he hoped. She looked at him with absolutely zero romantic interest, he described it as being seen as a relative rather than a potential partner. Rock coined his own version of the "friend zone" for the experience, calling it the "uncle zone". | © Netflix Is A Joke / YouTube
Emma Thompson had one of the more unexpected celebrity encounters in 1998, when Donald Trump called to ask her out on the very day her divorce was finalized. She thought it was a joke and turned him down without a second thought. Looking back, she's joked that if she'd said yes, American history might have turned out very differently. | © PowerfulJRE / YouTube
Years before she was an Oscar-winning actress, Nicole Kidman had a crush on Jimmy Fallon, and he had no idea. She visited his apartment, expecting a romantic connection, but Fallon spent the whole time playing video games and acting like it was just a casual hangout. He only realised she was interested much later, and by then, she had long moved on. | © A24
Even the biggest stars in Hollywood aren't immune to rejection, and some of their most embarrassing moments involve being turned down by fellow celebrities. From awkward hotel room encounters to decade-old crushes that were never returned, these stories prove that fame doesn't make dating any less complicated.
