A Complete Ranking Of All Of Kevin Arnold’s Romantic Interests On ‘The Wonder Years’

Inspired by Burnsy’s fantastic and epic Scientific and Important Ranking of Jerry’s Girlfriends on Seinfeld, I turned to one of my own all-time favorite shows, The Wonder Years. For a teenage boy, Kevin Arnold had quite a few romantic interests over the six seasons we knew him — not an insignificant feat considering he was in variable stages of going steady with his best girl Winnie Cooper throughout about half of them — so I thought the series was ripe for a definitive romantic interest ranking.

“But … But … You’re a WOMAN!,” I’m sure more than a few of you out there are saying right now. Yes, this is true. But all the more reason why I can objectively rank a bunch of teenage girls, and in some cases, adult women. My ranking is not just based on looks, (although it is partially based on looks) but also personality, kindness, sense of humor, and overall dateability.

Here’s the rules: This list does not include just requited love, but also instances in which Kevin was romantically interested in someone unattainable or vice versa. Also, for brevity’s sake, I listed just the first episode that the character appeared in, since several of Kevin’s love interests span beyond single episodes. I also kept it to the top 20, with the women who didn’t make the cut listed below:

Honorable mentions:

Cindy – Season 5 (“Full Moon Rising”): Kevin has a date with Cindy but breaks it when his friend Ricky Halsenbach gets his driver’s license, with some bullcrap excuse about his grandmother getting sick. Cindy later catches Kevin at the drive in and that was the end of that.

Gina Pruitt – Season 3 (“The Pimple”): Gina was a hot little number, the daughter of Kevin’s parents friends. He freaks out because he gets a pimple before her impending visit, only to discover that she’s got one too. Yuck — zits are gross. Off the list!

Waitress – Season 5 (“Broken Hearts and Burgers”): Clip show. Winnie loses her sh*t because she thinks Kevin is flirting with their waitress — who was actually trying to flirt with him.

20) Julie Aidem – Season 5 – “Of Mastodons and Men”

Julie was the WOORRRRSSSSST. Julie of the collar-fixing, and the smothering personality, the stupid foo-foo dog, and the family full of insufferable garbage women who emasculated her poor dad. Let’s hope Duke is still out there, somewhere.

19) Alice Pedermier – Season 6 – “Alice in Autoland”

After Kevin’s friend Chuck’s girlfriend Alice Pedermier dumps him, Alice connivingly tries to get with Kevin by dangling a “new” car in his face from her dad, a used car dealer. When Kevin rejects her she goes back to Chuck, claiming that Kevin came on to her and Kevin gets punched in the face. Alice was pretty awful.

18) Lisa Berlini – Season 1 – “The Phone Call”

Lisa Berlini was Kevin’s rebound crush after kissing Winnie Cooper in the pilot episode. Kevin finally gets up the nerve to ask Lisa to the dance and she originally says yes, until a better deal comes along in the form of a young Mark-Paul Gosselaar. Got dumped for Zack Morris? Sucks for you, brah.

17) Sandy – Season 5 – “Triangle”

I originally had Sandy, played by Carla Gugino, much higher on the list, but I don’t know why. Sandy was the devil. Yeah, Sandy was cute and liked making out as much as any red-blooded teenage girl — which is more than I can say for most of the prudes Kevin dated — but she was also Wayne’s girlfriend. You do not get in between brothers. That sh*t is diabolical.

16) Cindy Fleming – Season 6 – “Wayne and Bonnie”

Kevin meets Cindy (the second one on this list) at a diner where his newly estranged girlfriend Winnie is hanging out with some guy. Partly out of loneliness, partly out of jealousy, he invites her to his father’s work picnic but something seems off. As it turns out, Cindy was only in seventh grade. Whoops!

15) Inga Finnstrom – Season 5 – “Double Double Date”

Kevin recruits the help of Winnie Cooper to ask Swedish exchange student Inga Finnstrom out to the school dance, in return for Kevin helping her land a date with some guy named Matt. As it turns out, Inga wasn’t very smart. On the plus side? Neither was Matt. So after a failed attempt at a double date, Kevin and Winnie end up back together after their dumb dates ditch them for one another.

14) Susan Fisher – Season 3 – “Don’t You Know Anything About Women?”

There was really nothing wrong with Susan — kind of a dipsh*tty southern belle — who Kevin agrees to save a dance for only after he already agrees to go to the dance with his lab partner Linda. But there was nothing really remarkable about her either, other than nice hair. Typical Kevin.

13) Miss Hasenfuss – Season 4 – “Courage”

Because Kevin is too much of a giant pussy to get a cavity filled in the presence of his dentist’s foxy dental hygienist, Miss Hasenfuss, he asks that she not be there during his filling. He later has a change of heart after learning that Hasenfuss is taking his advice on going back to school to become a dentist.

12) Debbie Pfeiffer – Season 4 – “Little Debbie”

Aww, little Debbie Pfeiffer. I almost didn’t include Debbie in this list, the younger sister of Paul Pfeiffer. Kevin reluctantly takes Debbie up on her request to accompany her to her cotillion dance, only act like a huge dick, cruelly ditching out on her halfway through. He eventually comes back and makes up for it, so good job there, I guess.

11) Mimi – Season 4 – “Growing Up”

“So what’s Soleil Moon Frye been up to since Punky Brewster went off the air? Oh, you know, just growing enormous boobs.” Even though she was the daughter of the assy guy who got a promotion over Kevin’s dad, I don’t think I’m going to get many arguments ranking her this high.

10) Miss White – Season 2 – “Our Miss White”

Come on Kevin, really? What did you think the end game was, here. You were like twelve. Still, points for being a hot teacher.

9) Jessica – Season 5 – “Road Test”

Kevin lies about getting his driver’s license after he gets Jessica, played by a pre-The Crush, pre-Clueless, pre-Aerosmith videos Alicia Silverstone to agree to go out on a date with him. It never happens though, because his dad catches him trying to teach himself to parallel park in the middle of the night, but we sure can’t blame the guy.

8) Becky Slater – Season 2 – “Steady As She Goes”

OK now, before the lynch mob gets here, Becky Slater, real life sister of Danica McKellar, was NOT that bad. Sure, she was a total Tracy Flick type A personality and she beat the crap out of Kevin — but do you mean to tell me that little jerk didn’t deserve it? He pretended to go steady with her just to make Winnie Cooper jealous! Dick move, Arnold. Becky Slater, wherever your fictional self is today, I hope you just launched the most successful #YesAllWomen campaign ever.

7) Teri – Season 3 – “Summer Song”

During a trip to Ocean City, Kevin meets a hot older girl named Teri after Paul is forced to spend the trip indoors due to a skin rash (that is SO PAUL). Kevin and Teri make out under the boardwalk but then the next day she has to go back to Albuquerque with her family. Womp. Teri was played by Holly Sampson, who ended up with a successful career in the adult film industry. So there’s that.

6) Margaret Farquhar – Season 2 – “Square Dance”

Poor Margaret Farquhar: Professor of Biology, mother of six, friend to bats. I have a soft spot in my heart for Margaret Farquhar. Kevin reluctantly befriends the class weirdo after they get partnered up in square dancing class, but due to popularity/social classes, it was not meant to be and Kevin breaks her heart. You just know that in today’s world, Margaret Farquhar would have totally grown up to be Felicia Day.

5) Denise the Grease – Season 5 – “Frank and Denise”

Some of these girls on the list, I’m just like, I don’t even know. Kevin somehow finds himself in the middle of a relationship between Frank “The Stank” and Denise “The Grease” — Frank wants help getting Denise back and Denise for some unknown goddamn reason wants to make out with Kevin. The situation resolves itself with Kevin’s spleen still intact.

4) Linda – Season 3 – “Don’t You Know Anything About Women?”

Linda was the other half of the love triangle in the aforementioned “Don’t You Know Anything About Women?” Likewise I have a soft spot for Linda, as someone who spent my formative years as the “funny” short friend who routinely got bypassed for the tall, leggy blondes. Man, f*ck those girls. Anyway, Linda was super cute and by the time she got to college, TRUST ME, I’m sure she had the pick of dozens of guys. So in your face, Kevin Arnold.

3) Winnie Cooper – Season 1 – “Pilot”

Before you all revolt on me here for putting Winnie Cooper at #3, let’s talk this out. OK, while Winnie Cooper was cute and doe-eyed and pretty much the quintessential dream girl for an entire generation of boys navigating their way through the murky waters of puberty — Winnie Cooper was NOT a very good girlfriend.

How many Kirks and Rogers and 11th grade boys did she dump Kevin for over the course of six seasons? And even when they were together, she was kind of an irrational, moody pain in the ass. I mean, the guy followed her all the way to a summer resort job and she was all, “OH, I’m dating a lifeguard now, KTHXBYE.” You take #3 and YOU LIKE IT, WINNIE COOPER.

Still get choked up when I watch the pilot episode, though.

2) Madeline Adams Season 4  – “Ninth Grade Man”

Madeline was sophisticated, beautiful, elegant, and she even spoke French. Kevin really sh*t the bed on this one. First, he rejects Madeline’s advances in order to stay faithful to Winnie, who eventually dumps him for another guy anyway, and then has the nerve to use her to make Winnie jealous. What the hell was this guy thinking? And more importantly, what the hell was Madeline thinking? She must have had the lowest self esteem ever to get yanked around by a guy an entire head shorter than her.

1) Cara – Season 5 – “The Lake”

Cara was the ultimate summer dream girl. She was mysterious, elusive, effortlessly cool and smoked cigarettes. Summer romances have a certain fleeting bittersweet poignancy, so while we only briefly knew Cara, I’m giving her the #1 spot. CALLING IT.