Look, I knew Hollywood had plenty of famous men in age-gap relationships. What I did not expect was to keep running into literal A-list icons and men I genuinely never hear brought up in this conversation. So, here are the famous men’s relationships with much younger girls and women that look reallyyyy different in hindsight:
1.
According to The Guardian, Juliette Lewis dated Brad Pitt, Hollywood’s golden boy, for four years — “from the age of 16 to 20.” And mind you, this was all while Pitt was in his late 20s.
E! has also listed his co-star, Shalane McCall, as a rumored off-camera romance. Andddd Entertainment Weekly reported that 17-year-old Christina Applegate says she invited then-25-year-old Pitt as her date to the 1989 MTV Video Music Awards after they developed mutual feelings.
Juliette later told The Guardian that the relationship now “seems like a high-school relationship” and called Pitt a “stand-up, good guy.” Christina has also framed her VMA story as one about her teenage decisions rather than a condemnation of Pitt. But regardless, the timelines still hit very differently now.
2.
Paul Walker is often remembered by many as the warm, loyal guy from Fast & Furious, which is why this one genuinely caught me off guard. News.com.au reported that Jasmine Pilchard-Gosnell started dating Walker when she was 16, and he was 33. And when you look up pictures of them together and see how young she really looks, it just gets so, so much more eye-opening…
3.
People says Elvis was 24 when he met 14-year-old Priscilla Beaulieu in Germany and that their relationship began in 1959. After he returned to the US, Elvis convinced her parents to let her visit him and later finish high school in Memphis, where she eventually moved into Graceland. So, yes, one of the most romanticized celebrity love stories of all time began with a 14-year-old girl and a 24-year-old man, and it continued WITH her parents’ permission.
Priscilla herself has defended their early relationship, saying Elvis “was very kind” and “respected the fact [she] was only 14,” while insisting it was not sexual at the time. Unfortunately, that doesn’t make me feel even the slightest bit better 😭.
4.
The man behind one of America’s biggest comfort sitcoms was also publicly involved with a high school student at the height of his fame. The Los Angeles Times reported that Shoshanna Lonstein was 17 and a high school senior when she met 38-year-old Jerry Seinfeld. And this was not some secret relationship that resurfaced decades later — People literally put the couple on its cover while Shoshanna was still in school…
Seinfeld defended the relationship to People by saying, “Shoshanna is a person, not an age,” and described his interest in her as “very proper.”
5.
Wilmer Valderrama’s confirmed relationship timelines are all pretty uncomfortable… Newsweek reports that he dated Mandy Moore when she was 16 and he was 20. TikToker @demisculture even created a video pointing out that Valderrama and Lindsay Lohan were spotted together months before she turned 18, though it was never officially confirmed that they were a couple until she was 18 and he was 24. To top it all off, InStyle reports that Demi Lovato also met him at 17 and began dating him at 18, but this time he was 30. That ’70s Show is officially ruined for me.
And Demi has since revisited the relationship while discussing dating adult men as a teen on Keke Palmer’s podcast. Lovato literally asked, “Why was my boyfriend 30?” and said that once they reached 30 themselves, they realized, “That’s not OK.” They also brought up their song “29,” which is literally about their 12-year age gap.
6.
Everyone’s favorite Superman, fantasy nerd, and internet boyfriend, surprised everyone when his relationship with Tara King drew attention. People reported that 32-year-old Cavill was dating the 19-year-old college student and said he understood the 13-year age gap might “turn some heads,” and called that a “natural reaction.”
And then Elle literally asked him, “You’re dating a 19-year-old. I have to ask, What do you talk about?” Cavill answered, “Everything,” before saying the iconic phrase, “Age is just a number.” He then added, “But in this case, she’s fantastic.”
7.
Steven Tyler has long been treated like the ultimate wild rock star, but a civil lawsuit filed by Julia Misley (formerly known as Julia Holcomb) definitely changed some people’s minds about him. In her complaint, Misley alleged that Tyler began a sexual relationship with her when she was 16, convinced her mother to give him guardianship, and coerced her into having an abortion. Tyler has denied all of Misley’s allegations and, in court filings, has also raised defenses, including consent and his claimed legal guardian status.
Most of Misley’s claims were dismissed in April 2026, but one intentional infliction of emotional distress claim tied to an alleged 1974 incident remains set for trial. So, to be very clear: this is a civil case, Tyler has not been convicted or acquitted of a crime, most of Misley’s claims were dismissed, he denies her allegations, andddd one claim remains pending.
8.
Before you even get into the decades of Princess Diana discourse, the beginning of Charles and Diana’s story is already uncomfortable. Vanity Fair reports that 29-year-old Charles met 16-year-old Diana at Althorp in 1977 while he was dating her older sister, Sarah. Charles and Diana did not become a couple then, but he later remembered thinking “what a very jolly and amusing and attractive 16-year-old she was.” Literally, why did he expose himself?? 😭
And then, of course, there’s the engagement interview from hell. When Charles and Diana were asked if they were in love, Charles gave the infamous “whatever ‘in love’ means” answer. So even before the marriage fully began, the red flags were already screamingggg.
9.
If you grew up watching Hilary Duff as Lizzie McGuire, her relationship with Joel Madden gets more eye-opening every time the ages resurface. BuzzFeed has already reported that Duff was 16 and Madden was 25 when they started dating. But looking back, it is still wild to me how casually pop culture treated a Disney Channel teenager dating the lead singer of Good Charlotte.
Hilary’s 2025 song “Mature” has made that relationship resurface online, especially because of the line, “You’re so mature for your age.” However, Hilary has never said the song is about Joel. She has only confirmed it was inspired by a real, brief relationship with an older man and told Glamour, “Everybody speculates, but I’m not sure they got it right.” So I’m not saying “Mature” is about Joel Madden, but I am saying the internet heard that lyric and all thought the same thing…
10.
Prince is remembered as a genius, a romantic, and one of the most magnetic artists of all time, which is why Mayte Garcia’s own account of their relationship is so jarring. She was 16 when Prince saw a tape of her dancing and became interested in meeting her. According to coverage of her memoir, he began calling her, sending her letters and cassettes, and eventually brought her into his professional world as a dancer. Mayte also wrote that, after she graduated from high school and moved to Paisley Park full-time, Prince became her legal guardian. Keep in mind, Prince was more than 15 years older than her.
Then, when Mayte was 19, she recalled Prince telling her, “I think it’s time you got birth control.” Coverage of her memoir says this marked the beginning of their sexual relationship. Mayte remembered the moment as a “finally!” and has pushed back on the idea that she was vulnerable because she trusted and loved him. I don’t have anything nice to say, so let’s move on…
11.
Dane Cook and Kelsi Taylor became one of those age-gap relationships that had everyone immediately pulling out a calculator. People literally described Taylor as Cook’s 19-year-old “teenage girlfriend” while reporting on their 26-year age gap. Cook himself said they met “at a game night I host at my place,” were “friends for a while,” and eventually “upgraded to love.” I can’t believe someone would proudly admit this publicly 😃.
12.
Tyga is not exactly a beloved icon, but the Kylie Jenner timeline is too infamous to skip because I think people often forget how young she really was. People says Kylie was 17, and Tyga was 24 when dating rumors began swirling in 2014; Kris Jenner denied the relationship at the time. People then says Kylie and Tyga “went official” after she turned 18.
And then there was Tyga’s “Stimulated” music video, which starred Kylie shortly after she turned 18 and had WEIRD lyrics. Teen Vogue called the video’s subtext “unsettling,” and People noted that Kylie was cast soon after her birthday. Kylie later said on her reality show Life of Kylie that she ended the relationship because she was “really young” and did not want to look back feeling like Tyga “took something from [her],” but she did add that he was “really not that type of person.”
13.
Jay-Z and Beyoncé are now so solidified as an iconic power couple that people don’t want to acknowledge how young she really was when their relationship began. Beyoncé has said she met Jay-Z when she was 18, and that they started dating about a year later, when she was 19, and he was 30. But fans found evidence that they had been hanging out when she was 16, and Jay-Z claimed the same in an interview, prompting even more raised eyebrows.
Regardless, Beyoncé was at the beginning of her adulthood and superstardom, which made fans angry that she didn’t get more dating opportunities. A member of the Beyhive even wrote, “I’m her biggest fan, and it makes me so sad that she went from an overbearing father to dating a man who is 13 years her senior. She’s 40 and a mother of three now, but I want to live in a world where she had a clumsy dating history in the ’00s and dated around with Nelly, Usher, and Justin Timberlake.”
14.
Johnny Depp and Winona Ryder were romanticized for years as peak tragic Hollywood love — the tattoo, the red carpets, the engagement, the whole “Winona Forever” thing. People says Ryder was 18 and Depp was in his 20s when they got together, and that they got engaged within months. People also noted that Depp later dated Kate Moss, who was 20 when they met, while he was 31. Years after that, People reported that Depp and Amber Heard began a private relationship while she was in her mid-20s and Depp was in his late 40s. All the ages written out are truly something else.
And Winona’s own recollection makes the relationship feel even more formative. She called their split her “first real breakup, the first heartbreak” and said she was “completely lost” inside at the time. Winona has not condemned Depp — but her own words really drive home just how young she was.
15.
Sonny and Cher were packaged as this campy showbiz duo for so long that people forget how their story actually began. People reports that Cher was 16 and Sonny Bono was 27 when they met. Cher has said it was not love at first sight, and after she needed somewhere to live, she accepted Sonny’s offer to stay with him and work as his housekeeper. People also says they were living together by fall 1963, when Cher was 17, and Sonny was 28. But their relationship eventually became romantic…
Then Cher told the story in her own memoir, giving a much darker context. She described Sonny as controlling and said she felt “trapped” in a “loveless marriage.” She also wrote about standing on a hotel balcony and contemplating jumping before realizing she could simply leave him.
16.
Milo Ventimiglia has always had “TV crush” energy, playing men like Jess on Gilmore Girls and Jack on This Is Us. So it is a little jarring to remember that Entertainment Weekly reports he dated his Heroes co-star Hayden Panettiere when she was 18 and he was 30.
And Hayden has now revisited the age gap herself by saying, “At 18, I lived so much life that he almost couldn’t count me as being 18,” she told EW. She also stressed that her family knew Milo well and did not view the situation as inappropriate. I’m sorry, but I can’t get past the “he almost couldn’t count me as being 18” part.
17.
Kobe and Vanessa Bryant’s relationship is usually told as a whirlwind love story, but People exposed how whirlwind it actually was. Vanessa was 17 and still in high school when she met 21-year-old Kobe while working as an extra on a music video. People says Kobe sent roses to her school and picked her up in his black Mercedes, creating so much attention that Vanessa eventually finished her senior year at home. And within just six months of meeting, Kobe proposed.
Kobe himself even called it a “whirlwind romance”, while Vanessa has described meeting him as “love at first sight.” Although Vanessa has never condemned the way their relationship began, the timeline is still…interesting.
18.
Bradley Cooper and Suki Waterhouse started dating when she was 21, and he was 38. But then came the infamous Lolita photos. Vanity Fair published an entire piece about Cooper reading Lolita in a Paris park with his 21-year-old girlfriend while they took turns lying on each other’s laps. I’m sorry, but Lolita? With your 21-year-old girlfriend? While you’re 38? I fear the visual did not help.
Years later, British Vogue referred to “the Cooper years” before Suki described a very public situation from that period as “isolating and disorientating,” with a “dark and difficult” story behind it. Later in the interview, she spoke more broadly about her past relationships, saying the love she experienced in her 20s was “only ever a fetishization.” But now she’s happy with Robert Pattinson, so yay.
19.
John Mayer and Taylor Swift aren’t the most extreme age gap on here, but nobody can forget this one. People describes their romance as rumored and report that Swift was 19 and Mayer was 32 when they were linked. Fans have long connected “Dear John” to Mayer, and “Would’ve, Could’ve, Should’ve” only renewed the speculation because it references a past relationship from when Swift was 19.
A Swiftie even said, “John has/had quite the reputation with women and being a trashy boyfriend. I have no doubt he treated her poorly, not to mention the horrendous age gap with a barely legal Taylor.” Mayer later said the song “Dear John” made him feel “terrible” and “really humiliated.” In response to this, Taylor said, “How presumptuous! I never disclose who my songs are about.” So take it for what you will.
20.
Chad Michael Murray’s post-One Tree Hill dating life was already tabloid material, but the Kenzie Dalton timeline is incredibly odd. WECT described Dalton as an 18-year-old high school senior and reported that she and Murray were engaged. She had also appeared as an extra on One Tree Hill. So, yes, the adult star of a teen drama got engaged to a literal high schooler who was an extra on his show 😐.
WECT’s headline at the time was literally “One Tree Hill Star Engaged to Wilmington Teen”. I fear the 2000s were not even trying to be subtle.
21.
Zach Braff spent years playing the lovable, neurotic guy on Scrubs, which is why his relationship with Florence Pugh became such a viral age-gap conversation online. People reported that Pugh was 23 and Braff was 44 when they started dating. A fan even called out his age on one of Pugh’s Instagram posts, and she just replied “And yet he got it 👌🏽.”
To be fair, Florence has never framed this as a relationship she regrets, as she has repeatedly defended Braff and said the online criticism of their 21-year age gap included an “insane amount of abuse” that she got fed up with. But I would like to add that the public got even more judgmental when they realized how similar he looks to her father…
22.
Nicolas Cage is beloved in a chaotic, eccentric movie-star way, but two of his relationships have some seriously huge reported age gaps. People says Cage was 40 when he met 19-year-old Alice Kim while she was working as a waitress in Los Angeles. They married that July but got divorced over a decade later. Years later, in 2021, Cage married Riko Shibata, sharing a 31-year age gap.
And because this is Nicolas Cage, of course, it gets weirder. He proposed to Riko over FaceTime and FedExed her a custom black diamond engagement ring to Japan. And all I’m saying is that two marriages, each with an over-two-decade age gap, are two too many.
23.
Lastly, David Schwimmer is one of those names that I personally did not want to hear on this list 😣. People reported that Schwimmer was 50 while his then-wife, Zoe Buckman, was 31 in 2017; Glamour says they first met in 2007, when Buckman was working as a server at a London club, and Schwimmer was filming Run, Fatboy, Run. More recently, 59-year-old Schwimmer was photographed holding hands with 29-year-old Eliana Jolkovsky, a 2021 UCLA Medical School graduate, on the way to a dinner date.
Neither Schwimmer nor Jolkovsky has publicly confirmed a romantic relationship, but there is something jarring about seeing David Schwimmer’s name here at all. Sir, all we asked was for Ross and Rachel to stay together…
Which one shocked you the most, and who else belongs on this list? Tell us in the comments or the anonymous form below — your response may be featured in an upcoming BuzzFeed Community post!
