Celeb relationships with uncomfortable age gaps

What really matters in a relationship between two celebs? Love, obviously, but also compatibility, shared goals, emotional openness, etc. What doesn't matter so much? Age. At least it didn't matter to these Hollywood stars, who got together with romantic partners who, in some cases, could easily be their grandchildren. Put that way, it starts to get a little creepy, right? 

Well, on top of that, many of these relationships also created a dynamic where the celeb's kids all of a sudden found themselves in the same peer group as their step-parent, which has to be awkward. Then there are the relationships with downright alarming overtones, like Woody Allen's pairing with his ex's adopted daughter, James Woods' alleged preference for picking up teens, and Dick Van Dyke, who jokingly refers to his wife as his "child bride." Yeah… some of these are toe-curlers, for sure. Let's dive right in to these celeb relationships with uncomfortable age gaps. 

Michael Douglas and Catherine Zeta-Jones

Michael Douglas and Catherine Zeta-Jones have a lot of things in common. They've both won Oscars — he for Wall Street and she for Chicago. They also have the same birthday: September 25. One thing they don't have in common: the generations to which they belong. Douglas is on the cusp of the Baby Boom, born in 1944, but Zeta-Jones is more of a Generation X-er, born in 1969. Nevertheless, the quarter-century gap wasn't a problem when these two married in 2000.

They've since endured some serious health scares and rough patches — Douglas battled throat cancer and Zeta-Jones was diagnosed with bipolar disorder — but they've managed to avoid going the typical Hollywood route to Splitsville despite a period of separation around 2013. Speaking with AARP, Douglas shed some light on how they made it work. "It took work on both our parts. I don't think there's much chance of fixing a relationship if one of you is already out the door," he said, adding, "I think we're both mellower and wiser. That comes naturally with time. We count our blessings."

Hugh Hefner and Crystal Harris

As the creator of Playboy and the very mascot of the swingin' lifestyle it represents, the late Hugh Hefner hung out with much, much younger women for decades. Hefner married a total of three times — Fun Fact: His first union ended in divorce 1959 … or 27 years before his third wife was born. On New Year's Eve 2012, Hefner married lucky number three, Crystal Harris. She was 26 at the time, which was 60 years younger than the 86-year-old Hef. The wedding took place at — where else? — the Playboy Mansion.

While it probably wasn't a shock to many that Hefner got hitched to someone so much younger than him, when viewed alongside this other fact about the naughty mag mogul's life, it's easy to see a bit more of the cringe factor: Hefner had four children from his first two marriages. According to a 2017 Business Insider profile, they are Christie Hefner, 64, David Hefner, 63, Cooper Hefner, 27, and Marston Hefner, 26. With Hefner's widow Harris now 32 years old, as of this writing, that means that Hefner's two oldest children could have been her parents, and his two youngest could easily have been her siblings. Yikes. 

Woody Allen and Soon-Yi Previn

Writer-director Woody Allen and model-actress Mia Farrow were romantically involved for more than a decade. They never married, but Allen did help Farrow raise her adopted children. That all pretty much ended in 1992, when Farrow reportedly discovered Allen was cheating on her after finding pornographic Polaroids of another woman in Allen's apartment. Even worse: the pictures were of Soon-Yi Previn, Farrow's adopted daughter. 

Allen supposedly told Farrow that he was deeply in love with Previn and wanted to marry her. Not only was he essentially hooking up with his step-daughter, there was an age gap of about 35 years. Allen was 57 at the time, while Previn was estimated to be about 20 or 21 — she didn't have documents when Farrow adopted her out of an abusive Korean home, so her age was approximated with a "bone scan," according to Vanity Fair. Allen and Previn married in 1997 when he was 62 and she was (said to be) 27, but the legality of the union has done little to dispel the general public's feeling of unease about the whole thing. 

Frank Sinatra and Mia Farrow

Mia Farrow is no stranger to May-December romances. Her first marriage went down in 1966 when she was just 21 years old. The groom: Frank Sinatra. Farrow married Ol' Blue Eyes — in Las Vegas, of course — when he was 50 years old. That's a bigger gap than the 20-year difference she had with Allen, as well as the 16-year difference she had with second husband, composer Andre Previn.

Though their marriage only lasted two years, Farrow and Sinatra's romance lasted much longer, according to Vanity Fair, who reported that it continued "throughout [Farrow's] 13-year relationship with Woody Allen." But wait, it gets even more uncomfortable than that! Farrow has even played into, if not outright confirmed, rumors that she's not sure who the father of her son Ronan is, Allen or Sinatra, despite Allen's belief that he is the father, as the esteemed Maury Povich would put it. When asked "point-blank" by the mag whether Sinatra was Ronan's dad, Farrow replied, "Possibly." Awkward!  

Arlene Silver and Dick Van Dyke

The love life of the beloved, wholesome star of Mary Poppins is surprisingly rocky. Dick Van Dyke married his first wife, Margerie Willett, so long ago that their wedding was broadcast on a radio show — Bride and Groom — way back in 1948. They had four kids together and started to drift apart in the 70s, particularly when Van Dyke had an affair with Michelle Triola, his agent's secretary. They lived together both before and after Van Dyke's divorce from Willet was finalized in 1984, and remained a couple until Triola's death in 2009

But Van Dyke learned to love again, and in 2012, at the tender age of 86, he married 44-year-old makeup artist Arlene Silver, whom he met at a Screen Actors Guild Awards event in 2006. Despite the fact that she's 21 years younger than Van Dyke's oldest son, there's also this fun tidbit. While introducing her on Oprah: Where Are They Now? (via HuffPost), Van Dyke joked, "Ladies and gentlemen, this is my beautiful child bride, Arlene Silver Van Dyke." Hilarious! 

Celine Dion and René Angélil

It's not surprising that Celine Dion demonstrated her supernatural singing talents when she was just a kid in Quebec. She started to wade into singing professionally at the age of 12, thanks to the tutelage of her manager, the twice-divorced, 38-year-old René Angélil. The relationship was purely business for years until, in her late teens, her "feelings started to change," Dion told Access Hollywood. 

Dion even admitted that her mother wasn't pleased with the relationship at first, and that if she "reversed roles" with her own child, she wouldn't be thrilled, either. "I think of him and he comes [to me] with this lady who has kids and she's 45 and she think she knows best, [I'd be] like, 'Take your hand off of my son,'" Dion said. 

Fortunately, her own semi-scandalous to the manther/manager who was 26 years her senior worked out. They wed in 1994, started a family, and remained devoted to one another until Angélil passed away from cancer at age 73 in 2016.

Dyan Cannon and Cary Grant

Synonymous with words like "debonair," "dashing," and "movie star," Cary Grant could have had virtually any woman he wanted, even when he was old and past his prime. And the woman he wanted was starlet Dyan Cannon — he reportedly saw her in a guest role on a now-forgotten 1960-61 TV show called Malibu Run and used his Hollywood clout to contact her through her agent. He proposed a few times, and she eventually eloped with him to Las Vegas in 1965. At the time of the nuptials, Grant was 61, and Cannon was 27. 

But the ending to their story wasn't the type that Hollywood usually writes. According to EW, Cannon filed for divorce from Grant less than two years later after enduring his "harsher private side," which allegedly included him "criticizing" her, "spanking" her, and telling a friend, 'I'm going to break her like a pony.'" Um, what?! The pair was granted their divorce, but they continued co-parenting their daughter Jennifer. 

Billy Joel and Katie Lee and Alexis Roderick

If the old adage that rock stars are only in it to meet women is true, then Billy Joel just might be the biggest rock star of all time. His huge hit "Uptown Girl" was originally called "Uptown Girls," and it was about three women: models Elle MacPherson and Christie Brinkley, and singer Whitney Houston. Joel wound up dating MacPherson, and marrying and fathering a daughter with Brinkley. They divorced in 1994. 

Joel was five years older than Brinkley, but he decided to skew a lot younger with his next two marriages. In 2004, he wed Katie Lee, a food writer, chef, and former host of Top Chef. Born in 1981, she was about 32 years younger than Joel. They separated in 2009. Next up for Joel: a brokerage employee named Alexis Roderick. They married in 2015 — the bride was 33; the groom 66. Fun fact: Roderick is only about three years older than Joel's daughter, Alexa Joel, with whom she basically shares a first name. 

Tony Bennett and Susan Crow

Blessed with one of the best voices of all time, Tony Bennett is a legend of American music. The singer of "I Left My Heart in San Francisco" has left his heart long-term with three women. In 1952, he married Patricia Beech, and they had two sons; when Beech filed for divorce after Bennett allegedly cheated on her with actress Sandra Grant, Bennett married Grant and they had two daughters. Those two parted ways in 1979, and Bennett didn't take the marital plunge again until 2007. 

That's when he married the former Susan Crow, a woman 40 years his junior that Bennett says he met before she was born. Yep, this gets weird. In his book Just Getting Started (via Page Six), Bennett wrote that he posed for a photo in 1966 with Crow's parents at a show in San Francisco when her mother was pregnant. "It's a photo we all laugh about knowing the incredible turn of events that followed," the crooner mused. Perhaps even weirder? Grown-up Crow (well, 19-year-old Crow, to be honest) also first met Bennett in-the-flesh backstage at a concert— just like her parents! Nope, nothing creepy about those parallels at all.  

Patrick Stewart and Sunny Ozell

As the esteemed British actor best known for helming the Enterprise on Star Trek: The Next Generation and guiding the lives of young mutants as Professor X in the X-Men movies, Patrick Stewart has been married before, but the third time's the charm. 

In 2013, he wed Sunny Ozell after a few years of dating. The couple met in 2008 when Ozell was working as a waitress in New York restaurant Franny's. Stewart was starring in a production of Macbeth at the nearby Brooklyn Academy of Music when he wandered in for a bite. The age difference of about 38 years apparently didn't bother them, and of course, Stewart's status as an award-winning and highly recognizable veteran of TV and film probably went a long way in distancing him from every other old dude who slid his digits to Ozell on the check. 

As for the least uncomfortable part of this romance? The other love of Stewart's life was also part of the wedding: his BFF Ian McKellen officiated the ceremony. 

Emma Heming and Bruce Willis

Willis was half of one of the most famous celebrity super-couples of all time when he was hitched to Demi Moore from 1987 to 2000. But somehow, someway, the good-looking international movie star found love again after his divorce when he met Emma Heming in 2008. 

In an episode of People's List, Heming said that when she met Willis, she was surprised at how "charming" and "funny" he was, while he claims he pretty much fell in love at first sight with the much younger lady. They got married in Turks and Caicos in 2009 in front of many celeb guests, including Moore. Willis was 54 and Heming was 32 at the time. While their whirlwind romance sounds sweet, The Daily Mail couldn't help but point out how much Heming "looks very much like [Willis'] first wife Demi Moore — just 16 years younger," as well as the fact that she was "just a year older than Miss Moore's [then] toy boy husband Ashton Kutcher," who couldn't look less like the Die Hard star.  

Is it possible they were cradle-robbing just to spite one another? Regardless, Kutcher and Moore clearly didn't go the distance, whereas, as of this writing, Heming and Willis are going strong.

Hayley Roberts and David Hasselhoff

If Hayley Roberts would have taken her husband's last name, she would have been the second Hayley Hasselhoff in the family — with only 12 years between them, too! That's because Baywatch and Knight Rider star David Hasselhoff has a daughter named Hayley with ex-wife Pamela Bach. The couple divorced in 2006, but in 2017, the beloved-by-Germans pop star announced his engagement to Roberts after five years of dating. They made it official in July 2018. 

"I waited to propose because I thought I was too old for her," The Hoff told Hello! magazine. He was 63 and she was 36 when he popped the question.

The bride-to-be is not a celebrity, or at least she wasn't previously — she told The Sun that she was a shop clerk making minimum wage and living with her parents at their home in Cardiff, Wales. One night she was having a drink in a local bar with her sister when Hasselhoff walked by. She asked to take a picture, and they hit it off. Sounds like The Hoff attended The Tony Bennett School of Finding a Young Bride. 

Rosie Huntington-Whiteley and Jason Statham

It's hard to believe, but stone-cold British action star Jason Statham celebrated his 50th birthday in 2017. Rosie Huntington-Whiteley, a Victoria's Secret model and actress, is 20 years his junior. While there's a chance they don't understand each other's pop culture references, they seem to get along just fine. She told Self (via Us Weekly) that Statham is her "best mate" (that's British for "best friend"). The couple started dating in 2010, and got engaged in 2016.

If any of you would like to tell the tough-as-nails action star and former near-Olympic athlete how uncomfortable his relationship with Huntington-Whiteley makes you, be our guest. We're going to just move right along. 

Olivier Sarkozy and Mary-Kate Olsen

Mary-Kate Olsen began portraying Michelle Tanner on Full House (along with her twin sister, Ashley Olsen) when she was about 1 year old. Fun fact: at that moment in time, her future husband, Olivier Sarkozy, was 18. 

Sarkozy is a French-born banker (and half-brother of former French president Nicolas Sarkozy) who's been working in the financial industry in the United States since the early '90s … when Olsen was making direct-to-video money-makers such How the West Was Fun and To Grandmother's House We Go. 

When the unlikely couple married in 2015, complete with complimentary "bowls of cigarettes" for guests, Olsen was a 29-year-old designer and Sarkozy was the 46-year-old co-head of the Carlyle Group's Financial Services Group and father to two kids from his previous marriage. 

Amber Tamblyn and David Cross

By the time Amber Tamblyn got her major acting breakthrough, an Emmy-nominated starring role on Joan of Arcadia in 2002, David Cross had already established himself as one of the most important stand-up comics of his generation and a sketch comedy legend as the co-creator and co-star of HBO's Mr. Show with Bob and David. True love may not always match up people of the same age, but it often seems to pair up the coolest people. 

The duo welcomed their first child in February 2017. According to E! News, "They joked they named her 'Dauphinoise Petunia Brittany Scheherazade Von Funkinstein Mustard Witch RBG Cross Tamblyn-Bey jr.,'" but later revealed that her name was simply Marlow Alice Cross. Tamblyn was 33 and Cross was 52 when their little one debuted.

Sarah Paulson and Holland Taylor

There's a significant age difference — about 32 years — between Sarah Paulson, the Emmy-winning The People vs. O.J. Simpson: American Crime Story star and Holland Taylor, the Emmy-winning character actress most recently known for Two and a Half Men and The Practice. But they might as well be teenagers with the way they delightfully and unabashedly tell the world about their love. 

In an interview with Sandra Bernhard (via People) in January 2017, a 74-year-old Taylor said her 42-year-old partner makes her feel like the "luckiest person in the world." In her Emmy acceptance speech in 2016, Paulson cried out, "Holland Taylor, I love you!" and in an interview with The New York Times, she called Taylor "probably the most exquisitely beautiful woman I'd ever seen."

Katie Holmes and Tom Cruise

Cruise had been in the public eye for more than two decades — and previously married to Mimi Rodgers and Nicole Kidman — when he famously appeared on The Oprah Winfrey Show in 2005 and jumped up and down on a couch because he was so in love with former Dawson's Creek star Katie Holmes. 

A year later, the couple welcomed a baby daughter named Suri, and they wed later in 2006. Though the fairytale ended in divorce in 2012, it certainly began on a happy note. Holmes reportedly told Seventeen (via E! News) that when she was younger she dreamed about marrying the Top Gun star, who is about 17 years her senior. 

What's even more uncomfortable than Cruise essentially climbing out of a movie poster on a teenage Holmes' bedroom wall to marry her? The fact that she was allegedly assigned a Scientology chaperone (Cruise is a big-time practitioner of the controversial religion) during their time together. Totally normal, right?  

Harrison Ford and Calista Flockhart

Ally McBeal plus Indiana Jones equals true love forever — the two stars have been together for a really long time. They were a couple for more than eight years and had a son named Liam before tying the knot in 2010. It's Flockhart's first and only marriage, while it's Ford's third. He was with E.T.: The Extra-Terrestrial screenwriter Melissa Mathison for the better part of 20 years. Before that, he was married to Mary Marquant. 

Ford's wedding to Marquant took place in 1964 — the same year Flockhart was born, which is a fun fact they could enjoy simultaneously should they ever decide to merge his first wedding album with her baby book. That makes for a 22-year age gap between these two celebs, and probably a lifetime of hearing "You weren't even born, when I was doing [insert cranky old man references here]," for Flockhart.  

Alec Baldwin and Hilaria Thomas

As relayed in their New York Times wedding announcement, Baldwin approached Thomas, a yoga instructor, in a vegan restaurant and said, "I must know you." Then he gave her his business card, which is quite possibly the most old man way to ever approach a woman in the history of courtship. But it worked, no doubt in part, because he's one of the most recognizable actors on the planet. 

They played phone tag for a while, finally got together, and obviously hit it off. The couple with the 26-year difference in ages married in the summer of 2012. It's Thomas's first marriage and Baldwin's second — he was previously married to Kim Basinger, who is four years older than he is. And while we kid Baldwin for his old-fashioned pick up moves, don't think this relationship is just Thomas gently draping an afghan over Baldwin's lap and spoon-feeding him oatmeal. These two got right to work on making a family, and as of this writing, they have four kids already, and aren't ruling out a fifth. Sheesh! By any chance, did Baldwin's business card list him as the CEO of a baby factory? 

James Woods and Kristen Bauguess

Actor James Woods is a serial monogamist, and he has a type: women in their 20s. In the mid-2000s, he started dating a woman named Ashley Madison — no relation to the defunct adultery dating website (that we know of). She was the daughter of a friend; they'd reportedly known each other since Madison was five years old. Oh. Their relationship turned romantic when she was 19 and he was around 58. Shortly after his 2013 breakup from Madison, Woods coupled up with Kristen Bauguess, according to The New York Daily News. At the time of their romance's first blossom, Woods was 66 and Bauguess was 20, a mere 46 years separating the two. 

In 2017, actress Amber Tamblyn placed Woods' preference for younger women in a much darker light when she accused him of attempting to pick her up when she was 16 years old. After making the claim on Twitter (via The Daily Beast), which Woods denounced as "a lie," Tamblyn reiterated her claim in an op-ed for The New York Times, writing that after Woods propositioned her, she told him her age, to which he allegedly replied, "Even better." Granted, Woods clearly denied the accusation, but if it's true, it makes his continued courtship of very young women possibly the most uncomfortable out of anyone else on this list. 

Jacqueline Kennedy and Aristotle Onassis

The former First Lady of the United States was tragically and famously widowed in November 1963 with the assassination of her husband, President John F. Kennedy. She was 34-years-old with two young children, and a long life ahead of her. She remarried in 1968, to a long-time friend and Greek shipping tycoon Aristotle Onassis. 

While the former Jacqueline Bouvier's first husband was moderately older — 12 years — the age difference between her and her second spouse was a significantly larger 33 years. The marriage lasted seven years, ending when Onassis died in 1975, but according to a former assistant, it was an odd romance. In her memoir Jackie's Girl: My Life With The Kennedy Family (via People), Kathy McKeon wrote, "It was hard to tell by [Onassis'] business-like demeanor whether she was happy. … She and Mr. Onassis seemed like friends, not a couple." However, McKeon did confess, "They were very good to each other. They'd sit beside each other on the couch and rub one another's back." Whoa! Get a room, you too!

Donald Trump and Melania Knauss

The New York city real estate magnate turned reality TV star turned President of the United States was not yet either of the latter two things when he met Slovenian model Melania Knauss at a party in 1998. According to a GQ profile of Melania, Donald spotted her after arriving with another woman, whom he "sent … to the bathroom," so that he could chat her up. At the time, he'd been separated from his second wife, Marla Maples, for more than a year. Donald was 52, and Knauss was 28. 

The 24-year age difference didn't much matter, and the celebs married in January 2005. Since his rise to political stardom, there have been many seemingly uncomfortable revelations about the pair's marriage, but perhaps none more cringeworthy than those made by Donald himself. In particular, we're talking his infamous call-ins to shock jock Howard Stern's radio show, like the time when he and Stern cajoled Melania into admitting she was "almost" nude while the conversation went on, and another time when Donald joked about giving a then-five-months-pregnant Melania "a week" to get her body back into shape after having the baby. Oof. Anyone else feel like they need a shower? 

Jimmy Page and Scarlett Sabet

To be fair to Jimmy Page, he's always allegedly preferred his women to be extremely young. According to the book Hammer of the Gods (via Rosewater), the then-29-year-old guitarist reportedly spotted a 14-year-old girl named Lori Maddox at a Los Angeles nightclub, whom he secretly dated and copulated with (or more accurately, statutorily raped, since the age of consent in California has been 18 since 1913, according to Slate) for months. 

As of this writing, Page is now 45 years older, but the lady his life is only 13 years older than Maddox was during their allegedly illegal relationship. Page, 74, has been spotted in public canoodling with 27-year-old poet Scarlett Sabet. Dating since 2017, they've even made it Instagram official (a concept that Page is probably too old to understand). In other posts, Sabet, who is almost 50 years younger than the guy who it seems weird to call her "boy" friend, has heaped praise on the "Stairway to Heaven" axeman, labeling him her "inspiration," her "muse," "her mentor," and a "beautiful man" whom she loves "so much." 

David Foster and Katharine McPhee

David Foster is the soft-rock mega producer, songwriter, and arranger who transformed Chicago from a jazz-influenced classic rock band into an '80s lite-FM machine, and who also helped acts like Celine Dion, Kenny G, and Michael Bublé find their way to the speakers in every dentist's office in America. Katharine McPhee is the singer who combined Broadway-level pipes with supermodel-like good looks to propel herself to a second-place finish on American Idol (she lost to Taylor "Soul Patrol" Hicks somehow) and a successful acting career as the star of movies like The House Bunny and the TV shows Smash and Scorpion. 

But despite their 35-year age difference (he was born in 1949; she in 1984), these two make it work. It's probably their shared love of ultra-smooth schmaltzy pop that propels their romance. In 2018, Foster proposed to McPhee, which will make her his fifth wife, a club that includes songwriter Linda Thompson and Real Housewives of Beverly Hills star Yolanda Hadid. Foster and McPhee have known each other for years — he even played piano at her wedding to her first husband.

Richard Gere and Alejandra Silva

Richard Gere, who rose to fame portraying a male prostitute in American Gigolo and the world's nicest patron of female prostitutes in Pretty Woman, has been a silver fox for decades, so it's actually kind of hard to tell how old he is, and if his many conquests and relationships have been age appropriate. He was born in 1949, which would make him about 17 years older than his first wife, queen of the supermodels Cindy Crawford, and 12 years older than his second wife, Law & Order star Carey Lowell. In other words, Gere has a type, and that type is "younger than he is."

In 2018, Gere got married for the third time, to Spanish activist and Julie Bowen lookalike Alejandra Silva. He was about to turn 69, and she had just celebrated her 35th birthday. Fun fact: She's closer in age to Gere's son with Lowell, Homer James Jigme Gere (born in 2000), then she is to her husband. 

Mel Gibson and Rosalind Ross

Mel Gibson single-handedly destroyed his career with a string of ugly and alarming incidents. In 2006, he was arrested for suspicion of DUI, and uttered a slew of anti-Semitic remarks. Police also investigated him for domestic violence against his ex-girlfriend, Oksana Grigorieva, who he also told in a notorious leaked tape that he wouldn't mind if she were sexually assaulted by a group of African-American men that Gibson referred to by the worst word one can use to refer to African-Americans. 

It seemed highly unlikely that Mel Gibson would ever work in Hollywood again or find a woman who would pledge him her heart. But the star of the Lethal Weapon franchise somehow did both. In 2017, he earned an Academy Award nomination for directing the war movie Hacksaw Ridge, and months later he co-starred in the family comedy Daddy's Home 2. In early 2017, equestrian athlete and screenwriter Rosalind Ross gave birth to a son named Lars Gerard — her first child with boyfriend Gibson, and his ninth overall. There's a 34-year age difference between Gibson and Ross, as he was born in 1956 and she came into the world in July 1990, right around the time Bird on a Wire hit theaters.

Don McLean and Paris Dylan

Singer-songwriter Don McLean has recorded lots of albums, but he's undoubtedly best and most remembered for the track "American Pie." The 1972 song, which peaked at #1 on Billboard's Hot 100, is an extremely long folk song that tells the not-that-old-and-still-happening history of rock n' roll through clunky allegory and symbolism. (The Beatles, Bob Dylan, and Buddy Holly, among others, all merit a mention … or at least we think they do.)

Paris Dylan is an Instagram model and social media star, who, prior to the emergence of her relationship with McLean hit the tabloids, was best known for appearing on an episode of Catfish (she was an unwitting pawn in a scheme concocted by a third party that also involved NBA player Chris "Birdman" Andersen). She's also "really into 60s and 70s music," according to her website, which explains her interest in the guy who wrote and recorded "American Pie." First linked in November 2016, there's a 48-year age difference between romantic partners. McLean is 73; Dylan is 24.

Al Pacino and Lucila Sola

While the legendary star of Jack and Jill and Scent of a Woman never did say "hoo-ah!" (that's Scent of a Woman-ese for "I do"), Al Pacino has enjoyed a number of long-term, high-profile romances with famous women, including actresses Diane Keaton, Jill Clayburgh, and Beverly D'Angelo. When Pacino was with those women, they were all roughly in the same age range, but that can't be said for his most recent big relationship. 

From 2011 to 2015, Pacino dated an Argentinian actress named Lucila Sola. She was born in 1976, by which time Pacino had already starred in The Godfather, The Godfather: Part II, and Dog Day Afternoon (arguably his three best movies). He was born in 1940, which means at the time that he and Sola decided that they just wanted to be friends, he was 75, while she was 39. The 36-year age difference could have been a factor, although a source told The Sun (via the Washington Post) that they'd been fighting a lot and that both were "dedicated to their craft so sustaining a relationship was always going to be tough." So it goes.

Mick Jagger and Melanie Hamrick

Mick Jagger is the consummate, definitive rock star, both because of his ability to electrify and enchant a crowd (for more than 50 years now) with his singing and rooster-like swagger, and for how he is unabashedly non-monogamous. Among the women to whom Jagger vowed his (temporary) undying love and affection: model Jerry Hall, model (and future First Lady of France) Carla Bruni, model Anita Pallenberg, model Luciana Gimenez, and singer Marianne Faithfull. 

In June 2014, Jagger went for someone who didn't walk the runway or sing songs for a living, and got together with American Ballet Theatre dancer Melanie Hamrick. Things seemed to work out, because in December 2016, Hamrick gave birth to Deveraux Octavian Basil Jagger — her first, but the Rolling Stone frontman's eighth in all. He might even be a hands-on dad, offering in 2018 to take the kid on tour with him so that Hamrick could focus on her dance career. Their respective ages as of November 2018: He's 75, and she's 31.