“The Office” and other, similar shows and movies that feature cringe comedy have taught us that it’s possible to make even the most mundane things nearly impossible to watch. That said, cringe humor has always had a special way of searing love scenes into a viewer’s memory. The act of sex leaves a lot of room for complications, miscommunications, and inappropriate decisions. Intimate interactions are a minefield of potentially embarrassing moments, and any good screenwriter or film director should know how to utilize that minefield to make a scene particularly memorable.

Some scenes, though, end up being a little too memorable, and that’s when they become something that forces a cringey feeling. There are cringey sex scenes on our list that were probably always supposed to be mortifying (looking at you, “American Pie”) and there are cringey sex scenes on our list that just haven’t aged well (somehow also “American Pie”). We combed through comedies of the ’90s to find 11 love scenes that inspire acute second-hand embarrassment for anyone that’s craving a little cringe.

Okay, so the sex scene in 1996’s “Scream” isn’t entirely cringey upon first watch. The film’s main character, Sidney (Neve Campbell), is upset on the first anniversary of her mother’s murder, feelings that are exacerbated by a rash of murders that are suddenly overtaking the town. Despite her sadness, Sidney attends a party at a classmate’s house and steals away from the party with her boyfriend Billy (Skeet Ulrich) in order to process her feelings and apologize for falsely accusing him of her mother’s murder. Billy uses Sidney’s guilt to coax her into having sex for the first time. The scene itself isn’t particularly heinous: The two of them make out on a bed and the screen fades to black.

Cut to the end of the movie as Sidney finds out, in one of the “Scream” franchise’s biggest twists, that Billy has been behind all of the recent killings. Not only is it a wildly upsetting moment for Sidney, but it’s an apt metaphor for the kind of guy someone might date in high school who becomes a totally different person after sex has become a part of the relationship. When Billy and Sidney’s intimate scene is rewatched knowing Billy’s true nature, it is beyond cringeworthy. The first person Sidney ever slept with turns out to be a murderous lunatic — and not only that, he sexually assaulted and murdered her mother. It’s nearly impossible to sit still during this scene after knowing how the movie ends.

Woody Allen’s personal life has been considered cringeworthy by many since he separated from his then-longterm partner, Mia Farrow, in 1992 while admitting to dating her adopted daughter, Soon-Yi Previn. Despite this, he continued making films and enjoyed a prestigious professional reputation long after the scandal died down, with Allen and Previn even marrying in 1997. In 2017, however, statements by Allen’s adopted daughter, Dylan Farrow, alleging that Allen sexually abused her as a child garnered mainstream media attention. Since this second scandal came to light, Allen and his films have been ostracized and may be even more difficult to watch for anyone familiar with the details.

In 1995’s “Mighty Aphrodite,” which Allen wrote and directed, Allen plays a middle-aged man named Lenny who becomes obsessed with the biological mother of his genius adopted son. Lenny finds her, a woman named Linda (Mira Sorvino), and upon discovering that she is a sex worker, attempts to fix her life. While Lenny avoids a sexual relationship with Linda at first, he does eventually seek comfort in her arms.

Lenny, however, goes back to his wife the next day and soon loses touch with Linda. Woody Allen is 30 years older than Mira Sorvino and the age difference is … noticeable. Watching them get physical is decidedly uncomfortable, and it’s awful to see Linda tossed aside by Lenny (as she has been by many people in her life) after their one night together.

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).

“Groundhog Day” is meant to be something of a “grouchy guy learns a lesson about life” movie. Bill Murray’s brand could easily be characterized as “charming curmudgeon,” so it’s no surprise that he’s the one who stars as a meteorologist named Phil Connors. At the beginning of the 1993 movie, Phil is actually a terrible person who looks down on the people around him and lacks gratitude for good things. Phil soon finds himself stuck in a time loop, reliving Groundhog Day over and over and over again. By the end of the movie, he has learned how to be a better person through his love for Rita (Andie MacDowell), but not before he does quite a few terrible things during his time loops.

Phil, who is reveling in his lack of consequences while stuck in the time loop, decides to engineer a sexual encounter with a random woman who happens to be in Punxsutawney that day. During one loop, he asks her name, where she went to high school, and the name of one of her teachers, which puzzles her. The next day, he finds her again and uses the information to trick her into believing that he is an old classmate. It’s gross and underhanded, and while it’s probably supposed to be funny, it feels much more like someone taking cruel advantage of another person. It’s especially cringey when, during their night together, Phil continually refers to this woman as Rita.

As per its title, “Clueless” is all about a young woman named Cher (Alicia Silverstone) who often finds herself lacking in understanding. Cher lives a charmed life filled with weekly massages, fancy dinners, and Beverly Hills shopping sprees, and, while she’s generally a friendly person, she’s also — as the title implies — pretty clueless. Cher has a lot of strengths, but picking up on context is not one of them.

Partway through the 1995 movie, Cher develops a crush on her new friend Christian. Christian is a great dresser and charming as all get-out, and it makes sense that she’s into him. During the ska party scene, though, he’s clearly much more interested in the attractive men around him than he is in Cher (who is stunning in her own right). Cher has no idea and decides to invite Christian over on a night when her father won’t be home.

Cher is very excited to have sex for the first time, but every time she hints about it to Christian, he deflects to another activity or topic. When they are reclining on her bed, Cher tries to pose sexily for Christian and literally falls onto the floor. It’s embarrassing, and it becomes mortifying when Christian finally decides to leave. For the audience it’s even more cringeworthy because we know that Christian is gay and that Cher’s aggressive attempts at romantic instigation are up against an insurmountable obstacle. Somehow, the kissing scene with her ex-step-brother is less cringey.

A quintessential teen party movies of the 90’s, “Can’t Hardly Wait” depicts various interactions between people who have been in grade school together for many years. Eventually, these people aren’t going to be tied to each other anymore and everyone can just focus on nurturing the relationships they want to maintain. But, thanks to their childhood histories, the end of high school is also a time to revisit their connections and interact with people in new ways.

Denise (Lauren Ambrose) is best friends with the film’s main protagonist, Preston (Ethan Embry). She’s developed a surly, grumbling reputation in high school and prefers not to participate in group events. Even so, Preston convinces her to come to a big graduation party being held by a classmate. Denise is quickly abandoned by Preston, though, and after an unpleasant experience heads to the bathroom to clean up. Unfortunately for her, her old elementary school friend Kenny (Seth Green) is already in there, having gotten stuck thanks to the broken handle.

Denise is understandably repulsed by Kenny, a young man who has appropriated black culture in order to appear cool and imposing. But while trapped together, the two of them explore their past relationship and, despite their gross circumstances and Kenny’s mortifying affectations, have sex in the bathroom. How Denise is able to be repulsed by Kenny and seduced by him in one evening is something many viewers may never understand.

People probably think very differently of any movie that includes Kevin Spacey on the cast list ever since he was accused of multiple allegations of sexual misconduct in 2017. That said, 1999’s “American Beauty” had a high creepiness factor well before Spacey’s controversy came to light. The film follows Lester (Spacey), a suburban dad struggling with the existential dread that comes with middle age. Lester has a poor relationship with his wife (Annette Bening) and daughter (Thora Birch), which are further exacerbated by his obvious, cringey attraction to his daughter’s best friend, Angela (Mena Suvari).

At the end of “American Beauty,” Lester finally gets his shot with Angela. Angela is into it, most likely because she’s angry with her friend and feeling a fair bit of existential dread herself, and the two of them come very close to sleeping together. The entire scene has a high cringe factor if only because of the uncomfortable age gap between them. It’s not easy to watch a 40-something man take advantage of an underage teenage girl no matter what the circumstances, and after watching Lester’s behavior leading up to this scene, it becomes even more difficult. Luckily, Lester stops their interaction when he realizes that Angela is still a virgin despite her bragging to the contrary. Unfortunately, he can’t erase our memory of watching that scene.

Most of the 1997 movie “Booty Call” follows four friends— Rushon, Bunz, Lysti, and Nikki— throughout the course of an evening as they try to procure necessities and safe places for having sex. Bunz (Jamie Foxx) and Lysti (Vivica A. Fox) are the story’s B-couple but certainly the more prominent source of humor and levity in what is, at its core, a sex comedy. The two of them meet and develop chemistry, quickly leading to passionate interactions and attempts to get physical.

Eventually, Lysti and Bunz find themselves at the hospital (for something hijinks-related) and seek out a room with an empty bed; unfortunately the room also houses a patient with a full-body cast. Lysti, eager to consummate her new relationship with Bunz, goes so far as to poke the room’s occupant before deciding it’s safe to initiate sex.

It is hopefully not necessary to explain why a sex scene is awkward when two people are having sex in an occupied hospital room, but the movie takes the cringe factor even further when Bunz fails to maintain longevity for the sake of Lysti’s pleasure. After just a few pumps of his hips, Bunz is satisfied and Lysti is not. To make matters worse, the man in the full-body cast who’s also in the room is revealed to have been awake the whole time.

“Austin Powers: International Man of Mystery” often seems like an excuse for Mike Myers to make a fool of himself and hang out with a lot of beautiful women. Austin Powers (Myers) is supposedly sexually irresistible to women, but his swath of thick, oddly placed body hair, unfortunate dental situation, and tendency to turn everything into a sexual innuendo are far more cringey than appealing to the average viewer. Indeed, when Austin meets his new partner, Vanessa Kensington (Elizabeth Hurley), she seems just as turned off by him as anyone who might be watching.

There are several moments in which Austin’s sexual antics can cause sympathetic embarrassment, including his attempt to seduce Vanessa on a rotating, round bed. But the cringiest sex scene in the movie takes place toward the end when Austin encounters a group of attractive women in feathery lingerie while traversing Dr. Evil’s lair. Austin is easily pulled into their arms and bed, seemingly having the time of his life. His general mien is dorky, to say the least, but his reactions to the fembots aren’t nearly as cringeworthy as the fembots themselves. It may have flown in 1997 to have a character create sexy androids with guns that shoot from their boobs, but nowadays it’s a mortifying choice on the part of the people who made the movie. Is there anything more cringey than bad taste?

“The Big Lebowski” is such an important movie to some people that it actually inspired its own religion. This cult 1998 Coen Brothers comedy plops a regular, slacker-ish guy into the middle of a very high stakes situation simply because of a misunderstanding over his name. The man known to his friends as the Dude (Jeff Bridges) is forced to risk life and limb in multiple dangerous situations and it’s all because he has the same name as someone else.

One side effect of this experience that The Dude doesn’t mind so much is his acquaintance with Maude (Julianne Moore), daughter of the Big Lebowski. They meet when he becomes involved in her father’s affairs and effortlessly mesmerizes him. She then visits The Dude at his apartment and immediately seduces him into sex. It’s cringeworthy to see that The Dude is so susceptible to her influence.

It’s their pillow talk, though, that can make someone pull their hair out. He mumbles about his career history, briefly sparking her interest when he mentions the music business, only for her to lose it again when he explains that he was a roadie. These two people are on totally different wavelengths: At one point, Maude asks what The Dude does “for recreation” and at another, The Dude has a nasty coughing fit from smoking. It’s clearly a mismatch, and while that’s what she’s looking for, The Dude is totally in the dark.

It’s almost impossible to pick just one dicey sex scene from 1999’s “American Pie.” From Jim’s (Jason Biggs) intimate moment with an apple pie (an iconic scene that had to be tweaked to dodge an NC-17 rating) to Finch’s (Eddie Kaye Thomas) rollicking prom night with Stiffler’s mom (Jennifer Coolidge), there are lots of scenes that can make someone feel uncomfortable. The most awkward scene in the movie, though, has to be the webcam debacle during Jim and Nadia’s “study session.”

Nadia (Shannon Elizabeth), a beautiful, sexy foreign exchange student who goes to school with Jim and the gang, approaches Jim and asks if she can come over and study. Jim’s friends, upon learning that Nadia will need to change out of her ballet clothes when she arrives at Jim’s house, peer-pressure him into clandestinely filming her naked on a livestream for them (with Jim running to Kevin’s house so he can watch as well). Little do they know that the livestream ends up reaching the whole town.

Not only does Nadia take off her clothes on camera (against her knowledge!), but she also gets sexy with Jim after his friends convince him to take his chances with her. It’s mortifying to watch Jim dance naked for Nadia and get excited too quickly, but that embarrassment is magnified when scenes of Jim are interspersed with scenes of his peers and friends watching his humiliating hook-up.

Adam Sandler made a career in the 1990s playing characters on “Saturday Night Live” with abnormal affectations and accents. While he was only a cast member on “SNL” for about five years and fired in 1995 due to low ratings, Sandler soon moved on to Hollywood to make movies with his penchant for character creation. One of his most popular ’90s films was “The Waterboy,” in which Sandler plays a young Louisiana man named Bobby who was homeschooled by his mother (Kathy Bates) and who has a socially debilitating stammer. Bobby begins the 1998 movie working as a waterboy for a college football team and ends up a successful linebacker for another.

Bobby’s stammer is played for laughs throughout the film, both for the other characters around him and for the audience watching, although it’s actually not cool to make fun of a problem that many people suffer from and lack control over. Add to that a clearly fake Louisiana accent and you’ve got a character on screen who feels problematic in basically every scene.

Bobby is especially awkward, though, in a scene with his teen-crush-turned-adult-love Vicki Vallencourt (Fairuza Balk). Vicki kisses Bobby (with tongue) and he reacts by stammering more than he does in nearly any other part of the movie. After that, Vicki removes her top and shows him her chest. Bobby responds by saying “I appreciate wh-what you’re showing me right now” — while anyone who’s watching is most likely cringing.