Celebrity couples come in all shapes and sizes, but this time, we would like to focus on a different attribute. Yes, this is going to be an entertaining list because we are going to be focused on the age of these couples. Most specifically, we would like to talk a little bit about some of the craziest age gaps we have found in the history of celebrity couples. As you can imagine, there have been countless cases of older celebrities snatching up younger partners for all kinds of reasons. Of course, we are not denying that there is love in most of these instances, but there are a few iffy ones.
Here, we will have a little bit of everything—from the classic young actress falling for an older director, to the newer trend we have seen in recent years of young male models falling for older actresses, and even the occasional reality TV star. And yes, if you are someone who loves or hates the Kardashians, they will surely be featured on this list a couple of times. Politicians, technology tycoons, Woody Allen, we have taken the liberty to add all kinds of people to this list to show you that there is no limit to the types of people who maintain relationships, despite crazy age gaps.
20 Kate Beckinsale And Matt Rife (22 Years)
As you can probably imagine, this list is going to be filled with relationships that have age differences so ridiculous that we don’t know if we should feel happy for the older person or weirded out about the whole thing. That being said, let’s start our list strong by talking about the relationship between Kate Beckinsale and Matt Rife.
Everyone here should know who Kate is. If you don’t, she has been the star of several movies like Underworld, Pearl Harbor, and Total Recall. But more important than that is the fact that Kate is 44 years old. A few years back, she decided to start dating a guy who was only a few years older than her daughter. That guy was Instagram personality Matt Rife. Matt is just 22 years old, a.k.a. 22 years younger than Kate.
19 James Woods And Ashley Madison (40 Years)
If you are the kind of guy who dreams of scoring a younger girlfriend when you are older, James Woods is certainly the man in Hollywood you would want to look up to. This 70-year-old American actor has been everywhere and has done everything, and at some point, he decided that marriage wasn’t for him anymore and that dating life was where the fun was.
That being said, Woods showed the world that age difference didn’t really matter to him, as he started dating Ashley Madison who was 40 years younger than him. The two of them stayed together for a while, but since James Woods is a free spirit, he decided to make another change. This time he went even younger after breaking up with Ashley, as he is now dating Kristen Bauguess, who is 46 years younger than him.
18 Hugh Hefner And Kimberley Conrad (40 Years)
We cannot make a list like this without paying tribute to a giant among men. Hugh Hefner was a guy who lived in his own little world. And if any guy tells you he wouldn’t want to be Hef, you can be sure that he is lying to you. The creator of Playboy lived the life that every man who is not a priest dreams of living. But that doesn’t mean Hefner spent his entire life as a bachelor. Much on the contrary, this guy married three times. And, as you can imagine, the age difference was always a thing in his marriages.
His last wife, Crystal Hefner, was nothing less than 60 years younger than him. She remained married to him until he died, so on this list, we decided to add Kimberley Conrad, who was married to Hefner for more than 20 years, and the age difference between the two was around 40 years.
17 Kourtney Kardashian And Younes Bendjima (14 Years)
We could not complete this list without the occasional Kardashian entry, could we? The Kardashian in question this time is Kourtney, who supposedly started dating a man who is 14 years younger than her after they met at the Paris Fashion Week in 2016. The man in question is Algerian model Younes Bendjima.
Although it should not be any news that Kourtney was dating someone new, Younes seems to be quite the interesting guy. Unlike his girlfriend (ex-girlfriend, no one really knows), Younes was not born to wealth. He actually worked while he was young at his father’s restaurant before he began training to become a boxer. Nevertheless, Kourtney is not the only famous lady this boxer-turned-model has dated. He also apparently had a relationship with the British model Jourdan Dunn. Supposedly, Younes and Kourtney have broken up, but with these people, we can never know.
16 Doug Hutchison And Courtney Stodden (34 Years)
Doug Hutchison and Courtney Stodden were one of those couples that you barely needed to take a look at to know that, at some point, something would go wrong. Nothing against these two, it is just that the idea of them breaking up was already a given by the time they married in 2011. Just the story of how this relationship started was a little creepy. After all, they met in what many can only call a disturbing situation.
This relationship started when a 16-year-old Courtney decided to take an acting class taught by Doug. The guy didn’t realize she was only a teenager and started hitting on her online. And, the love was reciprocated. Sure, after finding out her age, Doug sought the approval of her parents, who were okay with the situation. Ultimately, the 34 years of age gap did not stop them from getting married nor from getting separated years later.
15 Michael Douglas And Catherine Zeta-Jones (15 Years)
One of the power couples of Hollywood, this is a relationship that is still surviving the ravages of time, but it would be hypocritical of us not to add it here. They might not have ultimately called quits, but Michael Douglas and Catherine Zeta-Jones have hit as rough a patch as any Hollywood couple we have ever seen.
For many years, they have tried to portray themselves as the perfect couple who loves their children, does everything right, and supports each other. However, the little charade came to an end after they had a fight and broke up for a short span of time. That little time was enough for Michael Douglas to throw wild and crazy allegations, like blaming his wife for the fact that he had gotten diagnosed with cancer. If that is not a failed relationship, we don’t know what is.
14 Bradley Cooper And Suki Waterhouse (17 Years)
Bradley Cooper is arguably one of the most sought-after actors in Hollywood these days. The man is good at what he does, and everyone recognizes it. Another thing that Bradley is very good at is wooing women. This man is like a magnet for beautiful women, and it is not hard to see why. Bradley is a good-looking guy, and he is about as rich and successful as people come these days. With that, it is no surprise that younger ladies would not care about their age difference when posed with the opportunity to date this superstar. That was the case with British actress and model Suki Waterhouse, who dated Bradley for almost two years.
The age difference between these two was a whopping 17 years. Unfortunately, according to the media that covered their breakup, the age gap was one of the reasons why they parted ways.
13 Johnny Depp And Amber Heard (23 Years)
We can say a lot about Captain Jack Sparrow, but one thing you cannot say is that this guy has bad taste in partners. Much on the contrary, Johnny Depp has an acute sense for finding and attracting beauty. His marriage to Amber Heard is the one that is most interesting for us. We are talking about the marriage between Johnny Depp and Amber Heard. To get this out of the way, the age difference between the two is quite staggering, as it is about 23 years. Yeah, that is a young adult. She could literally be his daughter.
Nevertheless, it seemed like the two of them were in love for quite some time, but things took a turn for the worse. Eventually, Amber called for a divorce. When it was all said and done, Johnny had to pay $7 million and had a restraining order issued against him.
12 Amber Heard And Elon Musk (15 Years)
One of the interesting things we found on this list is how common it is to find people who can be added to multiple entries here. People who like having older partners apparently cannot find a way to get away from this trend. We saw Mia Farrow a couple times, now it is Amber Heard’s turn. We heard about her marriage to Johnny Depp, which had a pretty terrible ending. But more recently, Amber was in a relationship with technology tycoon Elon Musk.
This must be something cool to say when you come home to tell your parents you are dating someone, “Yeah, I’m dating the person who is going to take humans to Mars and make us a spacefaring species. No big deal.”
Amber and Elon seemed to be a good couple, but unfortunately, the relationship only lasted one year as they decided to break up because of their conflicting schedules. The age difference between the two is 15 years.
11 Elon Musk And Talulah Riley (14 Years)
We talked about people who like having older partners, and we really meant it. Still, the same is true for folks who like having younger partners. Elon Musk showed with his relationship to Amber Heard that he was not new to dating younger women, and that fact was only confirmed when we looked a little bit into Elon’s dating history. Despite only being 46 years old, the South African businessman has already been through a couple of weddings, and one of them was to a woman who was 14 years younger than him.
The lady in question is British actress Talulah Riley. Musk’s former paramour might not be someone everyone knows, but she has been part of some big-time productions. She starred in Pride and Prejudice in 2005, but most people will remember her from playing Angela in the HBO production Westworld.
10 Tom Cruise And Katie Holmes (16 Years)
What was not wrong with this relationship? From the get-go, Katie Holmes had an odd attitude towards the whole thing, which only made it all the weirder when Tom Cruise declared to the world he loved that woman on The Oprah Winfrey Show...of all places. Perhaps the craziest thing about this entire ordeal was that Tom actually managed to terrify and surprise Oprah.
That being said, there are a lot of interesting factors that played out throughout this relationship. There was the Scientology angle that a lot of people gloss over, but even more frown upon. The speculation was that the church arranged this union, which made sense for the conspiracy theorists since they were married in a Scientology ceremony and the head of the church was Cruise’s best man. As for their age difference, it was a solid 16 years.
9 Kris Jenner And Corey Gamble (25 Years)
If there is one thing everyone must admit, it's that the Kardashian’s have done pretty much everything there is to do. In terms of dating, if we put together all the members of the family, there is a good chance that they have already had a relationship with all kinds of people. So, it is only natural that the matriarch of the family would have a relationship with a man who is a lot younger than her. How much younger? Try 25 years.
Yes, that is one-quarter of a century in age difference alone. This is the definition of people who are from completely different generations, so it is impressive that the two of them managed to get along as well as they did. Kris Jenner and Corey Gamble were together for almost 4 years before splitting up.
8 Luc Besson And Milla Jovovich (16 Years)
If you are a fan of action movies, and especially the zombie kind of action movies, there is no way you don’t know who Milla Jovovich is. This lady has pretty much single-handedly brought to life one of the best video game franchises of all time. Maybe not to life, but at least to the big screen as she played the impossibly powerful Alice in the Resident Evil franchise. The movies have received their fair share of criticism, but most of the complaints are unwarranted. After all, this is the kind of movie that you know what you are going to get when you walk into a theater to watch.
If blowing zombies' brains is not your thing, just don’t watch it. Now, back to the topic, before she was Alice, Milla became famous for her role as Leeloo in The Fifth Element. While filming that, she met and started a relationship with the director, Luc Besson. They were only married for a couple of years, and you can be sure that the 16-year age gap had something to do with that breakup.
7 Veronica Lario And Silvio Berlusconi (20 Years)
Believe it or not, the 20-year age difference was the least of the reasons why the marriage between Veronica Lario and Silvio Berlusconi did not work out. These two tied the knot in 2009, and before we go any further into this, we should at least tell those of you who do not know that Berlusconi is a former Italian prime minister and arguably the most controversial figure in the history of Italy. Seriously, you could go back to Roman days, and maybe you could pit Caligula against this guy to make it a good match when it comes to controversy.
To give you a little glimpse of the controversy we are talking about, when Veronica filed for divorce, she said that she "cannot remain with a man who consorts with minors" and "is not well." And yes, she was not lying. Google Bunga Bunga after you finish this list if you want a lesson in Italian history.
6 Jennifer Lopez And Casper Smart (18 Years)
If a lot of the guys on this list have proven that wealthy men always seem to manage to find themselves in relationships with younger women, some ladies prove the same point. We are not blatantly calling anyone a gold digger, but some of these relationships are just funny. However, this is not one of those cases. While they were together, it really did seem like Jennifer Lopez and Casper Smart were a good couple and that they were going to be together for a long time.
The age difference between the two is of about 18 years, and they faced a lot of pressure and criticism from the media and all other kinds of people for it. It was not unusual to see either one of them going up to microphones and defending their relationship, which lasted five years.
5 Frank Sinatra And Mia Farrow (29 Years)
Frank Sinatra was an interesting guy. Not only one of the greatest musicians of all time, but Sinatra was also a man who liked to enjoy life. He was no stranger to having affairs with women, and that might have been one of the reasons why a lot of his relationships did not work out. Not only that, his lifestyle was so crazy that there were even allegations that he had links to organized crime. Yeah, the life of Frank Sinatra deserves a documentary series of its own, but that is not what we are going to talk about here. We would like to talk about his first marriage, the one that didn’t quite work out so well. That marriage was to American actress Mia Farrow. The two of them married in 1966 and ultimately divorced in 1968. The age difference between them was 29 years.
4 Mia Farrow And Woody Allen (9 Years)
Since we were already talking about Mia Farrow and her failed marriage to Frank Sinatra, we thought it was worth an entry to talk a little bit about her failed relationship with Woody Allen. When she married Sinatra, Mia was a young woman who was barely into her early 20's. She still had a lot to learn in life and that, along with the age difference, had to be one of the reasons why she and Frank didn’t work out well.
That being said, 11 years after divorcing Sinatra, Farrow started dating Woody Allen, a relationship that would last a little over a decade. Their age difference is not that ridiculous when compared to others on this list, but nine years is still a lot of time. The thing here is that age certainly played a factor in their breakup as Woody left Mia to marry her adopted daughter.
3 Mia Farrow And Andre Previn (15 Years)
Well, if there is something we should take out of this list, it is the idea that Mia Farrow likes dating older guys. There is really no other explanation for her being on this list three times. We added the Woody Allen entry because the age difference was already big and the reason for their breakup was about as insane as it gets. However, she had yet another relationship in which a major age gap could ultimately have been a problem.
This time, we are talking about her 1970 marriage to German-American pianist Andre Previn. Andre is nothing less than 15 years older than Mia. Yeah, she likes older guys. Not only that, it also seems like she had a thing for successful guys since Andre is one of the best at what he does and has four Academy Awards and 10 Grammys to show for his success.
2 Ashton Kutcher And Demi Moore (15 Years)
What does Ashton Kutcher do these days? It seemed like he was going to be pretty big at the beginning of his career, but it all went downhill after he decided to steal Charlie Sheen’s show. And by saying that it all went downhill, we really mean all of it. After all, it all happened in 2011. It was the year he started playing the new main character of Two and a Half Men, and it was also the year Demi Moore announced to the world that she wanted out of their relationship.
This was quite the hit for everyone who liked the two of them as a couple since, after six years, we had already gotten used to seeing Kutcher and Moore together. Sure, their age difference of almost 15 years was something people were always discussing, but they still seemed to be a good couple.
1 Matthew Perry And Lizzy Caplan (13 Years)
When it comes to acting skill, this is one of the best one-two combos we have on this list. As most of you probably know, Matthew Perry became one of the most famous actors of his time when he played the role of Chandler Bing in what was arguably the longest show in television history, Friends. Now, we are just kidding. Friends was probably not the longest show ever, but since the show seemed to be always on television for such a long time, no one can blame us for thinking that.
On the other side of this couple, we have none other than Lizzy Caplan. She has not had as much mainstream recognition as her former boyfriend, but Lizzy had some fantastic projects of her own. The biggest one was the show Masters of S*x, which earned her a nomination for a Primetime Emmy Award.