The Most Awkward Love Scenes In '90s Comedies That Still Make Us Cringe

"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. Intimacy 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 love scenes on our list that were probably always supposed to be mortifying (looking at you, "American Pie") and there are cringey love scenes on our list that just haven't aged well (somehow also "American Pie"). We combed through comedies of the '90s to find love scenes that inspire acute second-hand embarrassment for anyone that's craving a little cringe.

Okay, so the bedroom 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 being intimate 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 physical intimacy 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 dangerous. It's nearly impossible to sit still during this scene after knowing how the movie ends.

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 be intimate 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 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, be intimate 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.

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 havi. 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 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 relations. 

It is hopefully not necessary to explain why a bedroom scene is awkward when two people are being intimate in an occupied hospital room, but the movie takes the cringe factor even further when Bunz fails to maintain longevity. 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 irresistible to women, but his swath of thick, oddly placed body hair, unfortunate dental situation, and tendency to turn everything into an 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 antics can cause sympathetic embarrassment, including his attempt to seduce Vanessa on a rotating, round bed. But the cringiest bedroom 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 attractive androids, 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. 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 love 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 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 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 becomes intimate with Jim after his friends convince him to take his chances with her. It's mortifying to watch Jim dance 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.