In Hollywood, both on and off the screen, it’s never been all that uncommon for older men to romance much younger women. Just look at how Roger Moore was playing an aging Bond by the end of his time as the spy, closing in on 60, and was still romancing beautiful young women in their 20s. Daniel Craig took an interviewer to task when asked how he felt about Bond wooing an “older woman” (Monica Bellucci) in Spectre, pointing out that Bond was simply chasing a woman his own age for once.

Sometimes big age differences are played down within the films, turning real life 20-30 year age gaps into 10-20 year ones on screen, but it’s still not unusual to see a significant age gap between two people in a movie that are in some sort of romantic and/or sexual entanglement. It’s also not only females who are the Mays in May/December romances– sometimes it’s an older woman going after a much younger man.

There are also times when the age gap itself isn’t that large, but the partnership still makes us feel uneasy. Whether it’s because the younger party is extremely young, or there is an inappropriate facet to how the couple is connected outside of their relationship– teacher/student, for instance– there doesn’t always have to be 50 years separating a couple for their pairing to be viewed as questionable.

Here are 18 Creepy Age Differences In Movies.

18. Maude and Harold – Harold and Maude

Harold and Maude 18 Creepiest Age Differences In Movies

Sure, the subtext of Harold and Maude is very endearing– a young man who doesn’t appreciate life has to learn from an elderly woman how to live life to the fullest. But the fact that their relationship turns romantic despite Harold (Bud Cort) being in his early-20s and Maude (Ruth Gordon) being 79 is difficult to look past, even if the movie plays their age difference up for absurdist comedic effect. Honestly, even the two just becoming close friends with zero romantic attachment would’ve still felt a bit inappropriate.

There’s also the matter of how much different it would be were it reversed, and a 79-year-old man was having a romance with a 20-something woman. A lot less people would’ve been able to see any underlying sweetness to the relationship if the sexes had been swapped.

17. Bob and Charlotte – Lost in Translation

lost in translation bill murray1 18 Creepiest Age Differences In Movies

To be fair, washed-up actor Bob (Billy Murray) and photographer’s wife Charlotte (Scarlett Johansson) are primarily just friends throughout the course of Lost in Translation and the pair don’t even so much as kiss. But that still doesn’t make it any less weird that this middle-aged man has decided to spend his evenings hanging out and drinking with a woman just out of college.

Of course, the pair’s time together isn’t completely innocent. They are frequently in close proximity of each other– heads on shoulders, things of that nature– even lying in bed together at one point. Raise your hand if you wouldn’t consider it at least somewhat cheating if your significant other was just lying around in bed with someone else. And then there is the matter of Charlotte being wildly jealous and hurt when Bob ends up sleeping with another woman.

Kudos to Bob for being the (mostly) mature one and keeping a relationship non-physical that could’ve easily went that way, but at the end of the day, not sealing the deal isn’t enough to keep Bob and Charlotte’s age difference from being a bit uncomfortable in terms of the relationship they develop.

16. Isaac and Tracy – Manhattan

Woody Allan Mariel Hemingway Manhattan 18 Creepiest Age Differences In Movies

It’s one thing to just write a movie where a 42-year-old man dates a 17-year-old woman. It’s another to cast yourself in the role of that man, and then find an actual teenage actress to play your love interest. Of course, Woody Allen would later go on to marry the adopted daughter of his longtime girlfriend, but we won’t get into all that.

In Manhattan, often considered one of Allen’s best films, he plays writer Isaac Davis, who is dating a 17-year-old girl named Tracy (Mariel Hemingway). Even just watching the couple walk around holding hands makes the skin crawl, but Allen doesn’t shy away from showing them lying in bed together watching TV and other more intimate interactions.

Yes, Manhattan is a movie about affairs and falling in love with friends’ mistresses and all kinds of sordid things of that nature. And it’s all told through the whip-smart writing of Woody Allen. But even if the two don’t end up together, and theirs is just one of many crazy relationships in a movie about crazy relationships, there is no denying how gross Isaac’s and Tracy’s relationship is.

15. Sam and Suzie & Kelly – Wild Things

Denise Richards Matt Dillon Neve Campbell Wild Things 18 Creepiest Age Differences In Movies

Maybe there are people out there who wouldn’t bat an eye at a guy in his late-20s (Matt Dillon) having a sexual encounter with an 18-year-old girl (Denise Richards). And maybe those same people wouldn’t think it’s any worse if a second 18-year-old girl (Neve Campbell) was thrown into said sexual encounter. However, when it’s revealed that the man is the guidance counselor at the high school that those two girls attend, it puts things in a whole different light.

The fact that the wrong-on-several-levels sexual activity that occurs in Wild Things is depicted in a scene that is among the more pornographic sex scenes ever seen in a mainstream, R-rated movie just makes it all feel even more seedy. That the scene also involves alcohol being poured onto– and drank off of– a high school girl’s breasts further ups the icky ante.

Worst of all, we don’t ever actually know the ages of either of the girls, just that they are in high school– we only assume that the one who ends up visibly topless is 18. Never bothering to explicitly say that the girls are of legal age just makes it that much creepier.

14. Finch and Stifler’s Mom – The American Pie series

Eddie Kaye Thomas Jennifer Coolidge American Pie 18 Creepiest Age Differences In Movies

And now we swap the sexes of an adult (Jennifer Coolidge) and a high school kid (Eddie Kaye Thomas) getting it on– only this time, the adult is in her 40s. Playing on the tropes of the classic film The Graduate, Finch loses his virginity on the same night that several of his friends do, only instead of it being with another high school student, he ends up being seduced by the mom of one of his classmates.

Most of American Pie sets up Finch as being wise beyond his years and far more mature than his friends, and finding lowly high school girls beneath him (not literally, of course). Fortunately, he stumbles across a frisky older woman who happens to have an affection for much younger men. The already-inappropriate pairing is made even more creepy when the woman insists that Finch call her not by her name, but instead refer to her as “Stifler’s mom” mid-coitus. Because everyone wants to hear their child’s name being used in a passionate tone and being reminded that they are a parent during sex.

13. Present-Day Henry and Past Clare – The Time Traveler’s Wife

Eric Bana Time Travelers Wife 18 Creepiest Age Differences In Movies

In The Time Traveler’s Wife, a guy named Henry (Eric Bana) randomly time travels against his will and has no control over where/when he goes– he just seems to travel mainly to times and places of some personal significance to him, which most frequently results in him visiting his wife Clare (Rachel McAdams) at various points in her past.

While it’s a common romantic notion to wish that you could’ve known your significant other as a child, that fantasy tends to involve you being a child, also. There is something unsettling about adult Henry spending time with his future wife while she is a young child (Brooklynn Proulx), knowing that he is going to be in love with– and make love to– her one day. The interactions between adult Henry and child Clare are never outright inappropriate, but it’s impossible for Henry not to look at child Clare through the same loving eyes he looks at adult Clare, which is what makes the whole thing so uncomfortable.

Still not convinced of the creepiness? Henry is naked at the other end whenever he time travels, so he initially appears to this 8-year-old girl as a nude adult man. So there’s that.

12. Will and Charlotte – Autumn in New York

Richard Gere Wynona Rider Autumn in New York 18 Creepiest Age Differences In Movies

Fans of Autumn in New York only want to remember the parts of the movie that are about a sweet man (Richard Gere) who shows a dying woman (Winona Ryder) love as she faces the end of her life, and the way they dramatically change each other forever. But that oversimplified summation leaves out a lot of important, less romantic details.

For starters, Will is a known womanizer of younger women. We get the impression that Charlotte is just the latest woman in her early-2os to be a notch in the bedpost of the nearly-50 year old. In fact, after having sex with her very soon after they meet, Will even comes right out and informs Charlotte that a real relationship isn’t in the cards for them– a class act, that one.

But taking her home and bedding her despite their age difference isn’t even the creepiest part– Charlotte is the daughter of one of Will’s (dead) ex-girlfriends. And he knew that going in!

At the end of the day, Will wanted to hook up with a younger version of a deceased former lover, and planned to immediately brush her aside for his next young conquest.

11. Harry and Marin – Something’s Gotta Give

Jack Nicholson Amanda Peet Somethings Gotta Give 18 Creepiest Age Differences In Movies

60-something Jack Nicholson hooking up with women in their 20s and 30s happened so often in real life that it’s hard to even bat an eye at it happening in movies. Yes, Something’s Gotta Give is a movie about an aging playboy who finally finds a woman his own age to fall in love with. Even so, that doesn’t stop the creepiness on display between Nicholson’s character Harry, and Marin, played by Amanda Peet.

What makes Harry and Marin’s admittedly brief on-screen time together so gross is how sexual it is and how much we have to see of it. Marin’s mother, Erica (Diane Keaton) is also dating someone younger; a doctor played by Keanu Reeves. But we largely only see their courtship via the two sitting side by side drinking wine together and things of that nature. Conversely, we’re “treated” to scenes of the 29-year-old Marin in her underwear straddling Harry as he places his 63-year-old hands around her almost-bare behind.

It’s one thing to see a couple of such mismatched ages out in public, engaging in light PDA– it’s another to get a glimpse at what’s going on between them behind closed doors.

10. Susan and Josh – Big

Tom Hanks Elizabeth Perkins Big 18 Creepiest Age Differences In Movies

Yes, we know– when Josh (Tom Hanks) gets physical and eventually has sex with Susan (Elizabeth Perkins), he’s technically in the body of a 30-year-old man. If it was considered creepy any time an adult woman had sex with an adult man who had the mind of a child, then most sexual encounters that have ever occurred in human history would be considered creepy.

That still doesn’t change the fact that Josh actually is a 12-year-old, and he was intimate with a woman in her 30s. When the couple are together it very much looks like a child in a man’s body, touching and making love to an adult woman.

There is also the matter of Josh seeming to do a terrible job at being an adult, and despite everything about him screaming “child” except for his outer shell, Susan still falls for him and is turned on by him. That is the part that is truly creepy. It’s fine to see a man with the innocence and wonder of a child and find it oddly charming– but to have it make you want to take your clothes off for him is more than a little strange.

9. Hana and Michael – The Reader

Kate Winslet The Reader 18 Creepiest Age Differences In Movies

While Big had the loophole of a kid who was physically an adult, we now start getting into the part of the list that involves adults outright having intercourse with actual underage people.

In the case of The Reader, we’re not even talking barely-illegal here– Hana (Kate Winslet) is 36 and Michael (David Kross) is only 15. It’s interesting how movies with an adult man and underage girl are almost always played (rightfully) elicit, while movies with an adult woman and underage boy can be framed as sweet and romantic. There is zero ambiguity here as to whether the two are physical, as they have sex multiple times throughout the course of the movie and frequently spend their time together naked.

As with other entries on this list, there is an extra layer of creepiness on top of just the age difference between Hana and Michael. It comes to light that Hana worked for a Nazi concentration camp, and was one of the people who helped select who went to the gas chamber. Her seeming ambivalence towards her actions is almost as unsettling as her ease at having a sexual relationship with a teenage boy.

8. Bill and Phoebe – The First Wives Club

Elizabeth Berkley Victor Garber Goldie Hawn First Wives Club 18 Creepiest Age Differences In Movies

Sometimes a man really, truly believes that the woman he is seeing is “of age” when in reality she is not. However, this is an issue that should only be faced by men in their early-20s dating women they believe are only a few years younger– not men in their mid-to-late-40s dating girls they think are 21. Dating girls several decades your junior, in ages hovering just above legality, is probably not the smartest way to save yourself that kind of trouble.

When Bill (Victor Farber) has an affair with hot young actress Phoebe (Elizabeth Berkley, proving she actually can act), he believes she is 21. However, his scorned wife (Goldie Hawn) and her friends discover that Phoebe is actually only 16. Even if you are somehow fully on Bill’s side on this one, and believe he didn’t do anything wrong by thinking he was seeing a 21 year old– putting the infidelity aside, of course– it still doesn’t make it any less creepy that a 40-something man was getting it on with a 16-year-old girl.

7. Sheba and Steven – Notes on a Scandal

Cate Blanchett Notes on a Scandal 18 Creepiest Age Differences In Movies

There is a lot going on in the acclaimed 2006 drama Notes on a Scandal, but at the heart of it is an inappropriate sexual relationship between a teacher in her 30s named Sheba (Cate Blanchett) and a 15-year-old student named Steven (Andrew Simpson).

While that relationship serves as the catalyst for most of the film’s events, it ends up taking a backseat to the older female teacher Barbara (Judi Dench) who develops an attraction to Sheba, Barbara’s eventually-revealed history of becoming obsessed with younger women, and the way she manipulates Sheba once she finds out about the illegal affair. On top of all that, another male teacher also tries to horn in on Sheba, even knowing that she is a) married, and b) already slept with a student.

Still, a guy trying to get into the pants of a teacher who he already knows is married and also having an inappropriate relationship with a student isn’t the creepiest thing happening in Notes on a Scandal, nor is the restraining order-worthy behavior of Barbara. A teacher having sex with her underage student trumps any other bad behavior occurring in the film by far.

6. Anna and Sean – Birth

Nicole Kidman Birth movie 18 Creepiest Age Differences In Movies

Birth is a bizarre movie about a woman named Anna (Nicole Kidman) whose husband dies, and ten years later, a 10-year-old boy named Sean (Cameron Bright)– also her dead husband’s name– comes to her and tells her he is her late husband reincarnated. While that should’ve been the beginning and end to that story, Anna finds herself believing the boy– and in an oddly short amount of time and with fairly little concrete evidence.

During the time that this obviously unbalanced woman is believing that a young boy is her reincarnated husband, there are of course a lot of creepy and inappropriate interactions between Anna and young Sean. Besides the two just spending a lot of time alone together– which is already off-putting given that it’s an adult woman spending a lot of time with a boy she hardly knows– there is a particularly hard to watch scene where Anna enters a bathroom where Sean is naked in the tub, and Anna then disrobes and joins him.

While we as viewers are supposed to be creeped out by this movie and scenes like the bathtub encounter, it doesn’t make any of it any less unsettling.

5. Connor and Mia – Fish Tank

Michael Fassbender Fish Tank 18 Creepiest Age Differences In Movies

Fish Tank is a critically-acclaimed but at times tough to watch film about a 15-year-old girl named Mia (Katie Jarvis) who is struggling through issues of anger and isolation. Where things first take a turn towards the cringey is when Mia’s mother’s 30-something boyfriend, Connor (Michael Fassbender) spanks Mia over an infraction– after having put on cologne and coming on to her, lest there be any confusion as to whether the action had lustful subtext for the man. The grossly inappropriate flirtation between the two eventually culminates in the pair drinking together and having sex.

Again, the age difference was already extremely inappropriate, but the boundary-crossing of it being a man sleeping with his girlfriend’s teenage daughter– after getting drunk with her, no less– before going and passing out next to the girl’s mother right afterward just puts the whole thing way over the line.

For what it’s worth, both Jarvis and Fassbender deserve major kudos for the strength of their performances here– but it’s exactly because they played their parts so well that Connor and Mia’s relationship is that much more upsetting to watch.

4. Paul and Jeanne – Last Tango in Paris

Maria Schneider Marlon Brando Last Tango in Paris 18 Creepiest Age Differences In Movies

The age difference between Paul (Marlon Brando) and Jeanne (Maria Schneider) may not seem especially drastic in the context of this list– he is 45 and she is in her early-20s– especially with how highly it is being ranked here. But there are a few key reasons why their relationship in Last Tango in Paris is deserved of being rated as extremely creepy.

For starters, the pair initially become involved in a sexual relationship that they intentionally keep completely anonymous– something about a 45-year-old man and a 20ish-year-old woman just having meaningless sex that isn’t about some unlikely romance they developed makes it that much more tawdry. We can’t help but wonder if Paul is even aware of Jeanne’s age at all, and if he is actually expecting her to be even younger.

But where things really take a turn is the infamous rape scene that occurs later in the film. We won’t get too specific here, but we’ll just say that butter was used as a lubricant– and that there is a specific reason why a lubricant was needed.

Schneider, who was only 19 when she made the movie, later said that filming the scene deeply traumatized her.

3. Humbert and Dolores/Lolita – Lolita

Lolita movie Stanley Kubrick 18 Creepiest Age Differences In Movies

Some movies are about a man who has a relationship with a girl that is way too young for him, but it’s something he’s never done before and won’t ever do again. Lolita, on the other hand, is about a man named Humbert (James Mason) who specifically has a thing for prepubescent girls. In fact, 40-something Humbert specifically rents a room at the home of a widow after he meets her daughter, Dolores (Sue Lyon)– aka Lolita– who is only in her early teens.

While later remakes of the film– based on “that book by Nabokov” as referenced by Sting– would make Lolita more overtly sexual and directly seductive, Kubrick’s original feels even more creepy by having Lolita engage in more innocent activities like dancing with a hula hoop, snapping her gum, and twirling her pigtails.

When it comes to men being sexually attracted to extremely young girls, there’s no “better” or “worse” way for it to manifest itself– but there is definitely something extra creepy about a man who specifically gets off on a young girl who acts like a young girl, rather than one with mature seduction techniques.

2. Edward and Bella – The Twilight series

Robert Pattinson as Edward and Kristen Stewart as Bella Twilight 18 Creepiest Age Differences In Movies

It doesn’t matter that vampire Edward (Robert Pattinson) is eternally in a teenager’s body because that’s the age he was turned into a vampire– his true age is 108, period. Just because you became a vampire as a teenager doesn’t mean that you get to spend centuries romancing teenage girls. Edward takes the famously creepy line from Dazed and Confused about how high school girls are great because they always stay the same age a bit too literally.

Perhaps we are supposed to feel less uncomfortable about Edward’s relationship with Bella (Kristen Stewart) in Twilight because he waits a few years to actually have sex with her. But that doesn’t change the fact that he not only started a romantic relationship with her when she was only 17, but even if he had waited until she was 25 to consummate their love, he’s still over 100 years old!

It’s the opposite of the movie Big, and is creepy for a whole different reason– his body is the right age, but he has the mind of a man deep into adulthood– which makes his copulation with Bella incredibly inappropriate.

We won’t even get into Jacob “imprinting” onto the couple’s newborn baby

1. Jareth the Goblin King and Sarah – Labyrinth

labyrinth 18 Creepiest Age Differences In Movies

Labyrinth never explicitly states Jareth’s (David Bowie) age. A manga sequel says he’s been the Goblin King for over 1,300 years, so take that for what it’s worth, but it’s easy to assume that he has been at it for a long time. This makes his desire to take 15-year-old Sarah (Jennifer Connelly) as his queen as creepy as his cod piece.

Fine, maybe Jareth is actually “ageless” and exists within a realm where time doesn’t pass in the same way it does for us, so being around for over a thousand human years doesn’t equate to his age being as such. But to that end, if Sarah were to accept his offer and become the Goblin Queen, she would presumably stay in her 15-year-old body forever– and there is something undeniably creepy about a magical being wanting to spend eternity with a lover who will never physically mature beyond the form of a 15-year-old human girl.

Jareth is the creepiest older person on this list because he doesn’t just want to be with a teenager now–he wants her to stay a teenager forever.

Which of these couples creeps you out the most?

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