Top10 Most Awkward First Times in Movies

Top 10 Most Awkward “First Times” in Movies

And you thought your first time was awkward! Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Most Awkward “First Times” in Movies.

For this list, we’ll be looking at embarrassing, uncomfortable, and just plain awkward times film characters have lost their virginities. Whether it’s awkward in a cute way, a funny way, or a cringeworthy way, it’s eligible for the list.

#10: Aimee Finicky
“The Spectacular Now” (2013)

While she’s often focused on the future, high school student Aimee Finicky manages to be quite forward with her more carefree boyfriend Sutter Keely. The pair have sex in her bedroom and engage in a very sweet, if awkward bit of first time lovemaking. The scene wonderfully captures the nervous energy of inexperienced sex, with all the laughs and pauses that come with the territory; making for a very naturalistic depiction of what it’s like to lose your virginity. It may not glamorous, but it can still be fun.

#9: Denise Fleming & Kenny Fisher
“Can’t Hardly Wait” (1998)

With a title like that, there was bound to be at least one first time in this film. Denise Fleming and Kenny Fisher are one-time friends who drifted apart and eventually end up locked in a bathroom together at a big party. Their friendship is rekindled during their time trapped together and an impromptu kiss leads to something else being kindled as well. Besides the awkward circumstances and locale of their first time, they also experience some doubts afterwards. However, if the caption in the credits is to be believed, they seem to make a habit of lavatory hookups; so to each their own!

#8: Bella Swan & Edward Cullen
“The Twilight Saga: Breaking Dawn – Part 1” (2011)

The whole “Twilight” franchise is built around the idea that sex is akin to having the blood sucked out of you by a monster, so heroine Bella Swan finally consummating her relationship with her beloved, Edward Cullen, was bound to be as awkward as she is. Losing your virginity is uncomfortable under normal circumstances, but even more so when your partner is actively trying not to inadvertently kill you due to super strength, and the fact that he wants to suck your blood. Bella’s first time is both supernatural and supernaturally hard to watch.

#7: Elio Perlman & Marzia
“Call Me by Your Name” (2017)

While they are boyfriend and girlfriend, that doesn’t stop the first time between teenage protagonist Elio Perlman and Marzia from being awkward. Despite their relationship, Elio is attracted to an older man, Oliver. The fact that Elio uses his first time with Marzia as a way to impress Oliver with his apparent maturity lends the pair’s riverside lovemaking an added air of awkwardness. Some people use one another when they have sex, but it’s extra rough when a person uses their loss of virginity as a way of manipulating someone else.

#6: Stacy Hamilton
“Fast Times at Ridgemont High” (1982)

A 15 year old student and pizza restaurant employee, Stacy Hamilton experiences plenty of talk about sex from her co-workers. However, her desire to lose her virginity leads to her a less than ideal first time. She tells Ron, a 26 year old customer, that she’s 19 and pursues him. After sneaking out of her house, they have sex in a softball dugout. Besides the decidedly uncomfortable locale, the fact that she loses her virginity through statutory rape is awkward for the audience as well. It’s probably better for both of them that he never followed up with her again.

#5: Christine ‘Lady Bird’ McPherson
“Lady Bird” (2017)

The titular figure in this coming of age film experiences plenty of turmoil throughout this story, including losing her virginity. When her nonconformist boyfriend Kyle claims to be a virgin, Lady Bird has sex with him. However, Kyle amends his previous claim afterwards and his lack of emotional involvement alienates Lady Bird, leading to their breakup. The fact that Kyle turns out to be such a jerk about this really colors the experience, making it a wholly negative one. Your first time is supposed to be awkward, but it shouldn’t involve someone lying to you.

#4: Juno MacGuff & Paulie Bleeker
“Juno” (2007)

Full time friends Juno MacGuff and Paulie Bleeker make the leap to part time lovers in this indie comedy. Although the unexpected pregnancy that results from their first time takes up the focus of the bulk of the film, and is plenty awkward in its own right, the deed itself is our focus in this entry. Although presented in a sweet fashion and with clear affection between the two, it’s still very tentative and short, which is definitely to be expected in most cases. Also, doing it on a reclining chair cannot be ideal for your first time.

#3: Everyone
“American Pie” (1999)

We honestly couldn’t pick a single character to focus on here, because they’re practically all cringe-worthy. After making a pact to lose their virginities before they graduate, four high school students go through a variety of sex-themed escapades. Though Oz and Heather’s first time is relatively normal, Kevin and Vicky’s is followed by a break-up, and Finch’s infamously occurs with Stifler’s mother on a pool table. Jim’s cavalcade of awkward attempts are arguably the worst though, from the pie incident, to the webcam debacle, to his eventual first time with band geek Michelle, who uses him for a one night stand.

#2: Andy Stitzer
“The 40-Year-Old Virgin” (2005)

The eponymous virgin of the title, Andy Stitzer has waited longer than most to have sex, thanks in large part to several awkward attempts in the past. His quest for love takes up the majority of the film, so when it does finally happen with his eventual wife Trish, it can’t help but feel like an anti-climax with how comically, if realistically, short it ends up being. Still, Andy and Trish are very cute together and the hilarious accompanying dance number does help capture the mood that many people are in after their first time.

#1: Fogell [aka McLovin]
“Superbad” (2007)

One of the most awkward characters ever committed to film, Fogell, better known by his mononym “McLovin,” has a wince-inducing first time. The nerdy teen manages to impress a girl at a party and proceeds to have incredibly cringey sex with her, with dialogue like, “I’ve got a boner!” and “It’s in! Oh my god it’s in!” McLovin’s “McLovin” gets interrupted when his two cop buddies barge in on the couple, leading to another slightly less uncomfortable conversation. The only thing more awkward than the scene itself is the fact that, since McLovin’s actor was 17, his mother had to be onset while this was filmed! We can only imagine the embarrassment!