Top 10 Most Awkward Moments in The Wonder Years

Kevin and Paul are initially excited when Sex Education is added to the curriculum. Their anticipation quickly turns to disappointment, as Coach Cutlip doesn’t paint the most flattering portrait of the female form. The boys thus decide to take sex ed into their own hands… no, not like that. At Wayne’s recommendation, they drop the textbooks and pick a copy of “Everything You Always Wanted to Know About Sex (But Were Afraid to Ask).” While acquiring the book is awkward enough, tensions escalate when Kevin’s mother catches them with it. Matters take an unexpected turn when Norma mistakes the copy for her own, giving Kevin a jaw-dropping glimpse into her sex life. Kevin finds that young boys aren’t the only ones with questions about sex.

This Season 5 bottle episode had plenty of awkward moments on the menu, from Paul’s mishap with a sloppy joe to Wayne’s confrontation with the school’s resident “maniac,” whose name turns out to be Florence. By far, the most uncomfortable subplot finds Chuck trying to ask out a classmate named Sheila. He chickens out after tucking his shirt as deep as it can go into his pants. Chuck does finally work up the courage, but he should’ve left his tray back at the table. After getting the words out, Chuck is delighted when Sheila reciprocates. The nervous Chuck can’t contain his jitters, though, loudly shaking his tray as he tries to seal the deal. Sheila ultimately backs outs, leaving Chuck twitching into a deep depression.

Life doesn’t get any less awkward for Kevin as he grows older. He simply finds new ways to embarrass himself. At a wedding, Kevin attempts to win a girl’s affection, but he spends most of the night trying to fend off unwanted come-ons from the feisty Aunt Muriel. Following a cringe-worthy dance, Kevin gets his hands on a bottle of champagne. He grows impatient waiting for Linda, though, helping himself to the bubbly. By the time Linda shows up, the bottle is empty and Kevin is starting to feel guilty about being unfaithful to Winnie. What’s more, Linda has found someone else to party with. Kevin leaves Linda with a parting gift that won’t be coming out of her dress anytime soon.

This episode introduces Peter Armbruster, an overweight classmate nicknamed “Pig.” He’s played by Michael Ray Bower, who you might recognize as “Donkeylips” from “Salute Your Shorts” and Monica’s prom date on “Friends.” When the popular kids invite Kevin to work on the yearbook, he’s pressured into coming up with a quote for Peter. He spouts out, “Let’s eat!,” which he later substitutes with the even less flattering, “Oink! Oink!” The guilt eats away at Kevin as he becomes closer to Peter while the popular kids throw him under the bus. As stomach-churning as the ordeal is, Peter and Kevin end things on good terms. Peter is comfortable in his own skin and doesn’t care about status, although the same can’t be said about Kevin.

While Kevin and Peter part on friendly terms, Margaret Farquar is another story. When Kevin gets paired with the weird girl for square dancing, he can’t shake her off. Margaret won’t leave Kevin alone, eating with him at lunch and even showing up at his house uninvited. Eventually looking past her bat obsession, thick glasses, and three pigtails, Kevin comes to enjoy Margaret’s company. While he doesn’t have romantic feelings for her, Kevin still wants to be friends… secret friends. Margaret can be oblivious, but she knows when she’s being insulted. With several others watching, Margaret leaves Kevin with five blunt words that still sting: “I Thought You Were Different.” Kevin reveals that Margaret grew up to be a successful professor and mother, but their relationship never receives emotional closure.

When Kevin dreads receiving “the talk” from his father, he stumbles into an even more uncomfortable experience. Building a treehouse, Kevin and Jack spot neighbor Donna working in her garden. The father and son both find themselves drawn to her umm… “tomatoes,” which is awkward for more than a few reasons. Although they avoid discussing the encounter, the elephant in the garden becomes harder to ignore when Norma has Donna over. Does it get any more cringe-inducing than that? Well, Norma later comes up to the treehouse and gets a good look at the view. The silence is more excruciating than anything else. At least Kevin avoids having the talk with Jack, who merely tells his son that he’s too old for treehouses.

“The Wonder Years” was always authentic in its exploration of generational gaps, especially when it came to conservative Jack and rebellious daughter Karen. Their conflicting worldviews reach a boiling point when the family learns that Karen is living with her boyfriend Michael, played by David Schwimmer. Hey, another “Friends” actor! Sharing a roof is one thing, but learning that Karen sleeps in the same bed as Michael is more than Jack can handle. While Kevin finds that Michael is a loving boyfriend, Jack turns his back on Karen nonetheless. Rather than wrap everything up in twenty-two minutes, the showrunners let tensions stew for several episodes. Jack and Karen do make amends the following season, but not before sitting through another painful dinner.

Sometimes you need to lower your expectations. The upbeat Miss Haycock learns this the hard way when she takes over the eighth-grade glee club. Although the glee club sounds about as appealing as fingernails on the chalkboard, Haycock is confident that she can turn them into five-star singers in time for the Spring Sing concert. Haycock’s vibrant smile turns to a look of devastation when the boys tell her that they’re not ready. This motivates Warren to break out his concealed singing chops, giving the glee club a spark of hope. At the concert, however, Warren’s voice changes mid-performance, throwing everyone else off. Paul has a sneeze attack, Doug falls over, and Haycock flees in humiliation, never to be seen again.

Kevin and Winnie’s relationship had no shortage of awkward moments. If we had to pinpoint the hardest to sit through, however, it would have to be their seven minutes in heaven. Actually, they don’t make it to seven minutes and the experience is anything but heavenly. Having recently become a couple, Kevin and Winnie are still figuring things out. So, when they’re selected to enter the make-out room at a party, all of their insecurities are suddenly put on display. After a few moments of quiet tension, Winnie runs away without an explanation. Kevin and Winnie share a passionate private kiss later that night. Before we can get to the happy resolution, though, we must endure Kevin’s embarrassment as the partygoers stare at him alone.

Kevin’s Crush on Miss White, “Our Miss White”
It Never Would’ve Worked Between Them

Caught In the Middle of Frank & Denise, “Frank and Denise”
As If Kevin Doesn’t Have His Own Relationship Problems to Deal With

Double Double Kevin’s In Trouble, “Double Double Date”
Two Exes on a Double Date, What Can Go Wrong?

Alice, Kevin, & Chuck, “Alice in Autoland”
From Bad, To Worse, To Somehow Even Worse

As awkward as Kevin’s relationship with Winnie could be, that’s nothing compared to his love-hate dynamic with Becky Slater. Still carrying a torch for Winnie, Kevin thinks he can let Becky down gently. When Kevin suggests that they remain friends, the sweet, innocent girl he thought he knew responds with her fist. Kevin’s problems with Becky are just beginning. While they were going steady, Kevin made some rude remarks about his fellow classmates. Becky proceeds to share Kevin’s comments, resulting in Winnie ruffing him up. Later, Kevin accidentally gives Becky a Valentine. After he tries explaining the mix-up, she goes from punching to almost running him over with her bike. Ironically, Becky finds a new love as a result, but Kevin can’t catch a break.