Celebrity Hookups We Never Knew About Until Much Later

The following article includes brief references to allegations of domestic abuse, sexual harassment, and homophobia.

We don't know if celebrities date more than the average person, but it seems safe to say that folks in Hollywood are never starving for romantic attention. Or it at least appears that way when you consider the thousands of dates, hookups, flings, and relationships covered by the tabloids each year. Seeing as how those are just the connections we know about, a true picture of the celebrity dating game may never truly be had. Even their online dating profiles — which often happens by way of the super-selective and very secretive dating app Raya — are kept under strict lock and key.

But we are here to talk about a specific kind of celebrity romance, ones that we didn't know about at the time they were happening, but on which someone spilled the beans at a later date. We are using the term "hookup" loosely, but none of the connections on our list resulted in anything serious. Most of them were flings — more than a date or two but short-lived and on the downlow. Many of the celebrity hookups that the world knows about are juicy and sometimes pretty scandalous. But it's those lesser-known ones that are really salacious, surprising, and sometimes just straight up silly. And we didn't even include some of the most random hookups, like Madonna and Tupac Shakur (what?) or Oprah Winfrey and Roger Ebert (double what?). 

Here is a selection of the most interesting celeb hookups that we didn't know about until much later.

Cher's love life has been anything but predictable, and that is one of the things we love most about the iconic singer. Never one to be locked in by cultural norms, Cher has dated all sorts of men, including many who were significantly younger than her. As of this writing, this includes her most recent paramour, music exec Alexander Edwards (40 years younger), as well as rocker Richie Sambora, actor Val Kilmer, baker Rob Camilletti, and producer Josh Donen. The latter two relationships were quite public, particularly the one with Camilletti, which supposedly ended due to the media scrutiny. Cher loves a camera, but it turns out she can also keep some of her dalliances secret — temporarily, at least.

For example, Cher had a brief romance with Tom Cruise a few years after meeting him at Madonna's 1985 wedding to Sean Penn but didn't open up about it until a 2008 interview with Oprah Winfrey. When they met, Cruise was 23 and on the up-and-up thanks to roles in films like "All the Right Moves" and "Risky Business." Cher was 39, but the 16-year age difference was by no means a dealbreaker for the stars, who crossed paths again at a White House event the next year. Details on the exact timeline are still unknown, with Cher telling the Daily Mail in 2018, "We didn't go out till way later, but there definitely was a connection there." On a 2013 episode of "Watch What Happens Live," Cher confessed that Cruise was one of the best lovers she had ever had.

Tom Brady's love life receives ample amounts of scrutiny nowadays, but that wasn't always the case. Back in the day, Brady was actually free to date in peace without the glare of the paparazzi or scrutiny from his millions of fans (and haters). This was, of course, well before he became known as the GOAT and became arguably the most discussed football player of modern times. 

Brady's first widely covered relationship was with model and actor Bridget Moynahan, with whom he shares his oldest son, Jack. The pair dated from 2004 to 2006 and split shortly before Moynahan found out she was pregnant, which is one reason the situation garnered a lot of media coverage. The other? Supermodel Gisele Bündchen, who Brady had already started dating by the time Moynahan's pregnancy became known. As most people under the sun know, Brady and Bündchen went on to get married, have two kids, and maintain a high-profile marriage for over a decade before their surprising split in 2022. 

But we are not here to talk about Brady's baby mamas, so much as the women who predated them. One of them was Tara Reid, who reportedly had a short fling with Brady in 2002. We don't know many details about their time together but do know their connection was romantic, because Reid discussed that aspect on Australian radio show "Kylie and Jackie O" in 2014. She said they'd locked lips and that Brady is "pretty good-looking," but did not spill any juicy details (via Us Weekly).

FKA Twigs met her ex-boyfriend, Shia LaBeouf, filming "Honey Boy," and they dated for almost a year from 2018 to 2019. This has become LaBeouf's most notable relationship because FKA Twigs sued LaBeouf in 2020, alleging physical, verbal, and sexual abuse at the hands of her former partner (the lawsuit is still ongoing as the trial has been delayed until November 2023, per Insider). After initially denying the allegations, LaBeouf admitted to at least some wrongdoing in a 2022 interview on Jon Bernthal's "Real Ones" podcast, without giving specifics. Needless to say, the relationship between FKA Twigs and LaBeouf did not end well, but the vast majority of the actor's famous exes have remained mum on the topic. The exception is Karolyn Pho, a former girlfriend who detailed similar claims.

The actor's list of exes is long, and LaBeouf has a history of hooking up with his co-stars. This has included Margaret Qualley, with whom he starred in a music video for Qualley's sister, as well as his "Transformers: Revenge of the Fallen" co-star, Isabel Lucas. It also includes Megan Fox, another of LaBeouf's "Transformers" franchise co-stars. "Look, you're on the set for six months, with someone who's rooting to be attracted to you, and you're rooting to be attracted to them," he told the now-defunct Details in 2011 (via E! News). "But the time I spent with Megan was our own thing, and I think you can see the chemistry onscreen." Fox confirmed the hookup in a 2018 "Watch What Happens Live" appearance.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

Given his astronomical level of fame, Justin Timberlake couldn't really keep secrets about his dating life if he tried. Case in point: the worldwide furor that erupted when he got caught holding hands at a bar with "Palmer" co-star Alisha Wainwright, prompting rumors he was cheating on wife Jessica Biel. Before Biel, Timberlake had widely scrutinized relationships with Cameron Diaz and Britney Spears, and he's been linked to everyone from Ashley Olsen to Alyssa Milano. One of Timberlake's more surprising hookups was with singer Fergie, which only came out years later. It's not surprising that two attractive young talents, both of whom first found fame as children (she on "Kids Incorporated" and he on "The All-New Mickey Mouse Club") would link up, but their age difference makes it rather peculiar.

The duo dated sometime in 1996 and 1997, although reports have suggested it was a brief fling. "He was 16 and I was 23," Fergie told the Australian Courier Mail many years later (via Us Weekly). "It was before he got real heavy with Britney." Seven-year age differences can be nothing, especially in Hollywood, but the difference between being a younger teen and a mid-20s adult is striking. It's worth noting that the age of consent in California is — and was back then, as well — 18, which makes it extra surprising that Fergie would admit to the fling, but we also can't think of many grown women who would want to spend romantic time with a teenage boy, even if he was as iconic as Justin Timberlake.

Both Julia Roberts and Matthew Perry have colorful dating histories, and we actually think they seem like a much better match than either of them do with a lot of their previous and subsequent choices. Roberts has been married to Danny Moder for more than two decades now, but it took her a while to find her forever person. Before Moder, she dated Liam Neeson, Dylan McDermott, Kiefer Sutherland, Jason Patric, and Benjamin Bratt. She was also briefly married to Lyle Lovett, who she married in 1993 after only a few weeks of dating (30 years later, we are still processing this one). All of Roberts' relationships received considerable media coverage, save for her short romance with "Friends" star Matthew Perry.

Perry — who has also been linked to Lizzy Caplan, Yasmine Bleeth, and Lauren Graham — wrote about his relationship with Roberts in his memoir "Friends, Lovers, and the Big Terrible Thing," and admitted that he was the one who ended things. Their brief fling started when Perry was tapped to court Roberts for a guest appearance on "Friends." After he sent three dozen roses and a surely hilarious card, Roberts signed on for the show, and for romance. The whole thing lasted only a couple of months due to Perry's insecurities. "I had been constantly certain that she was going to break up with me," he wrote in the book. "... So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."

Amanda Seyfried is happily married to fellow actor Thomas Sadoski, who she met in 2015 when they co-starred in the Off-Broadway play "The Way We Get By." They reunited to film the movie "The Last Word" later that year, confirmed a relationship in 2016, and were married in 2017. Now they have two kids and live on an idyllic farm in Upstate New York. Before she was married, Seyfried had a couple of relatively public long-term relationships — one with her "Mamma Mia" co-star, Dominic Cooper, and another with actor Justin Long. She also had flings with Ryan Phillippe and Josh Hartnett, both of which were covered by the tabloids. Somehow, Seyfried was able to keep her brief romance with Alexander Skarsgård a secret for years before spilling the beans in a 2011 Elle interview.

Even though we would shout about a relationship with the hunky Skarsgård from every rooftop in town, we are sure Seyfried had her reasons for staying mum. Most likely, it was the notoriously private Skarsgård who insisted on the covertness of the romance, since he has traditionally been much less publicly available than Seyfried. We don't know the exact timeline of when the pair dated, but it was around the time Seyfried was involved with Cooper, which would place the hookup sometime between 2007 and 2010, per People. "We dated. He's super funny, but I was too involved with Dom [Cooper]," she told Elle. For his part, Skarsgård had a child with his girlfriend, Tuva Novotny, in March 2023.

For this one, we are going way back — but don't fret, because this is one of the juiciest hookups on our list. We also didn't hear about this connection until 2009, which is when the late Cloris Leachman released "Cloris: My Autobiography." Never one to mince words, Leachman was upfront about her past escapades, including her hookups. One, in particular, made the news cycle: her liaison with fellow legend Gene Hackman. According to the book, Leachman and Hackman were both shooting movies in San Francisco when they shared a single night of passion in the 1970s. They were staying at the same hotel and after crossing paths, decided to get dinner, which led to more.

"As we moved into the main course, it was as if a cosmic wind enveloped us. Some giant space magnet was pulling us together," Leachman wrote (via Vulture). "We didn't finish the meal. We went upstairs, flew into bed and made love. It was epic. And the next morning, Gene went back to his film and I went back to mine. I haven't seen Gene since that night, but I remember well the feisty lad he was." 

We should note that Leachman was married to writer, producer, and actor George Englund from 1953 to 1979. Her book details Englund's affair with Joan Collins, so the marriage was clearly not without other infidelities. Hackman — who has been married to pianist Betsy Arakawa since 1991 — was wedded to his first wife, Faye Maltese, at the time of the Leachman encounter.

Gerard Butler is another actor who admitted to a hookup with Brandi Glanville, and since he similarly confessed on an episode of "Watch What Happens Live," we have Andy Cohen to thank for yet another juicy celebrity admission. Butler's comments came after Glanville had already discussed their hookup, so let's backtrack first to Glanville's initial confession. She let it slip in a 2012 appearance on "Watch What Happens Live," back when she was still on "The Real Housewives of Beverly Hills." She kind of had no choice since she was playing "Plead the Fifth" and had already used up her non-answer on the first question. Glanville named Butler as her most famous hookup but said that things lasted only a week before fizzling out.

Butler played it cool when a TMZ paparazzo tracked him down, asking "Who's Brandi Glanville?" in a way that made it unclear what went down. But then, ever true to his probing nature, Cohen asked Butler about the hookup when he appeared on the Bravo talk show years later. After first pretending to redirect the conversation, Butler fessed up. "I had no idea who she was. And I kept saying, 'So, what do you do?' She goes, 'It doesn't matter. It's not important,'" he explained on the 2018 episode. "... Anyway, we hung out, we had fun, and then I never saw her again." 

Glanville was seemingly incensed by these comments and went on a Twitter rant that might just explain why some men don't publicly acknowledge hooking up with her.

Elliot Page spilled a ton of secrets in his 2023 book "Pageboy: A Memoir," which is exactly what we expect from a juicy celebrity tell-all. In some instances, Page kept people's names a secret — for example, he never named the famous actor who threatened to forcefully have sex with him while also making homophobic remarks back when Page was pre-transition and gay-identified. For some reason, Page protected this person's identity, but that doesn't mean he didn't name names in other places in the book.

One of the stories in the book that has received the most media attention involves a fling that Page had with fellow actor Kate Mara. Mara was okay with Page discussing their affair, even though it was previously unknown to the public and Mara had not previously discussed being a part of the queer community. "The first person I fell for after my heart was broken Kate Mara," Page wrote (via People). "She had a boyfriend at the time, the lovely and talented Max Minghella." While the fling was kept secret from the public, it should be noted that Minghella was aware of what was going on and supportive of Mara's exploration. We don't know exactly how long the two hooked up for, but it was around the time of "X-Men: Days of Future Past," which came out in 2014.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

Look, we don't know what was in the water fountain at Bayside High, but the "Saved by the Bell" set was apparently a randy place! The late Dustin Diamond aside, there is no one on the main cast who didn't have some sort of romance with a fellow co-star. And since the cast was not extremely large, that means there was a lot of overlap. While we don't know exactly what went down between Mark-Paul Gosselaar and Tiffani Thiessen, we do know that they had some sort of romance, as previously mentioned. But Gosselaar is not the only co-star Thiessen had her eye on — she also had the hots for Mario Lopez, Gosselaar's on-screen rival and off-screen friend.

Lopez and Thiessen's brief relationship has been known for a while, at least since Lopez published his memoir "Just Between Us" in 2014. In the book, the actor detailed how the pair hung out for a while before becoming official, after which he cheated. "I thought that being loyal to Tiffani was the right thing to do," he wrote. "But I can't say that I was capable at that age of following through on my noble intentions." 

Executive producer Peter Engel discussed the relationship in his own 2016 memoir "I Was Saved by the Bell: Stories of Life, Love, and Dreams that Do Come True," which included providing details on the dissolution of the romance. "He was in his dressing room, making out with an extra, and Tiffani came in, catching him red-handed," Engel wrote (via Radar).

Andy Cohen has come up a lot on this list as someone who knows how to get celebrities to spill their juicy hookup secrets, and we cannot believe the number of big-name stars that have been willing to play his brutal "Plead the Fifth" game on "Watch What Happens Live." Cohen mostly speaks abstractly about his own dating life as a single gay dad, though we know about his ex-boyfriends, Clifton Dassuncao (who Cohen dated for two years) and John Hill, with whom Cohen co-hosts "Andy Cohen Live" on SiriusXM. We also know that Cohen may have once made out with Cheyenne Jackson, which Jackson alluded to on an episode of Cohen's talk show, but Cohen either didn't remember or feigned not remembering.

One person we know Cohen for sure remembers hooking up with is NSYNC hottie Lance Bass, since both he and Bass discussed the rendezvous in the press. Cohen first made the admission in a 2014 "ET" interview, when he was asked about a famous person that people would be surprised he hooked up with. The next year, Bass clarified that things were not as intense as people assume. "I can just tell you right now, there was no Andy D going in my B," he said on SiriusXM's "Dirty Pop" (via ET). "I'm not going to tell you what went down ... but it's not what people are thinking." Cohen again acknowledged the hookup in a 2015 "The Howard Stern Show" interview, but also refused to go into the details.

Singer Aubrey O'Day does not shy away from publicity, even if it's less than flattering, and so we were not surprised when she decided to tell the world about an affair she had with a married man. We were surprised, however, that the man in question was apparently Donald Trump Jr., oldest son of the former POTUS. It was first reported in 2018 that Trump had allegedly cheated on his then-wife, Vanessa, with O'Day, best known for being a member of the band Danity Kane and more recently for reality TV appearances. In fact, it was when O'Day was a cast member on "Celebrity Apprentice" in 2011 that she began communicating with Trump via social media, per an interview O'Day did with Michael Cohen for his "Mea Culpa" podcast.

O'Day spilled other juicy details in the interview, such as how the pair's first sexual encounter supposedly went down in a gay bar bathroom while she was hosting an evening there. "Everybody is in a g-string or less, and I was just, in my soul, like, 'There is no way the man that I've seen suited-up for the past couple months is going to show up here to see me in this lovely land that I get to be in,' and he did," she said. 

We are just as shocked as O'Day was, seeing as how Trump has arguably been no friend of the LGBTQ+ community. For her part, O'Day called out this apparent hypocrisy before graphically describing the encounter later in the interview.