From 1988 to 1993, ABC aired 113 episodes of The Wonder Years, a coming of age story about a boy named Kevin Arnold. The show took place in 1968 and pulled at the strings of nostalgia for a viewing audience that grew up at the same time. Over the course of its six seasons, the audience saw Kevin grow up and deal with issues ranging from problems between his parents and bullies at school, to larger scale stuff like the politics of the era and the ramifications surrounding the Vietnam War.
But the A-Number-One concern of young Kevin Arnold almost always revolved around the opposite sex, and as a result, he went through a lot of relationships/crushes/kisses and heartbreak. Here are the ten best relationships - real or desired - of Kevin Arnold's youth.
10 Denise Lavelle (Amy Hathaway)
Denise "the Grease" Lavelle appeared during the show's fifth season and represented something different - the unobtainable dream girl with whom Kevin rooted against his own success. Though she took a shine to Calvin/Kevin, he spends most of their time together trying to push for her reconciliation with Frank the Stank.
Though he looks at Denise with desire, the end voiceover shows that he truly did want love to win out here as he hopes news of her eventual divorce is untrue, this having been an example of his own romantic maturation.
9 Margaret Farquhar (Lindsay Fisher)
In what could have been a friendship or maybe even more, Kevin Arnold again shows us just how flawed (and real?) a character he could be. After being paired up to square dance with Margaret Farquhar, Kevin shows off the cruelty of adolescence and does everything he can think of to distance himself from 'the weird girl' in an attempt to save face.
Sure Margaret had three pigtails and talked too much, but she was also interesting and genuine, two traits largely absent most Junior High kids.
8 Madeline Adams (Julie Condra)
The ultimate temptress, Madeline Adams showed up at a time when Winnie and Kevin were trying to make the long-distance thing work all the way across town. New girl Madeline immediately shows interest in Kevin, and Winnie encourages him to be nice, as she, now going to Lincoln, knows how hard it is to be the new girl.
Kevin resists though, spurning Madeline's advances for several episodes until Winnie dumps him for someone else. The rebound with Madeline is short-lived however as she utters the unthinkable line: "I never saw what the big deal about Winnie Cooper was anyway." Her invalidation of Kevin's life long crush is more than he can take and he abruptly ends things.
7 Mrs. White (Wendel Meldrum)
In season two, Kevin Arnold was hot for teacher, and while - for obvious reasons - this never materialized into anything real, it was a strong enough fantasy to leave a lasting impression on a 12-year-old boy and inspire him to do something he hated in an attempt to impress his crush, and that's an important step for any adolescent.
6 Becky Slater (Crystal McKellar)
Becky Slater was Kevin's first steady girlfriend and eventual nemesis. Kevin goes out with Becky just to make Winnie Cooper jealous and as a result of this despicable move, following their eventual breakup, Becky makes it her mission to punish Kevin. She continues to play adversary through the next couple of seasons and is an important reminder of past sins.
5 Teri (Holly Sampson)
Kevin's first summer fling came during his family vacation at the start of the third season. On the beach, he met an older girl named Teri, and for a couple of days they walked the beach and went to photo booths and did all the necessary montage activities for a teen romance of this kind.
And while it was fleeting, and Kevin seems happier about the proof the pictures provided of his summer conquest than anything else, it was still a nice pairing with no heartbreak at the end. She even wrote him once, and he still keeps the letter.
4 Linda Sloane (Maia Brewton)
Linda Sloane is arguably the best fit for Kevin of anyone on this list - both in height and personality - but she was cursed with a good sense of humor, a winning personality, and none of the glamor that instead drew Kevin to the vapid Susan Fisher.
He takes Linda, who clearly likes him to the dance, and while there, pines for Susan, resulting in the loss of both girls. Well, the only real loss here is Linda.
3 Sandy Tyler (Carla Gugino)
The only reason that Sandy Tyler doesn't check in even higher here is that she is dating Wayne when she and Kevin fall for each other.
This is truly one of the only girls on the show that seemed a really good fit for Kevin, though as we learned through her relationship with Wayne, her interest could have a shelf life. Sandy dumps the older Arnold boy in order to be with Kevin, but in a rare move of solidarity, he sticks by his brother's side.
2 Winnie Cooper (Danica McKellar)
Winnie Cooper, the girl next door, the love of his life, the #2 entry on the list. Wait- what? For those who haven't revisited The Wonder Years recently, you probably have a more glowing memory of Winnie than you will upon rewatch.
While she is the ever-present object of Kevin's desire for six seasons, she also at times leaves him for another guy, gets into a jealous fit about a waitress, and throws out mixed signals. All that said, these things just make her more real, and all the more heartbreaking when we learn in the finale that Kevin and Winnie do not end up together in the end.
1 Cara (Lisa Paige Robinson)
Here's the one the Kevin really screwed up, and Cara knew better. Kevin and Cara meet at the drive-in while his family was vacationing at the Lake. While they only had a few days together, and Cara straight up tells him she shouldn't trust the summer kids that come to town, she falls for Kevin anyway.
Their chemistry feels sincere, but when his family returns home, in typical Kevin-style, he turns his attention back to Winnie. Come Christmas, Cara sends him a card that he can't be bothered to respond to. The following summer, frustrated with Winnie he returns to the lake to find Cara, but she's wisely moved on. If only he'd sent her a Christmas card...