“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:
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.