Top Ten Fictional High School Girlfriends

grease header 560x372For the record, Grease is many wonderful things. It has great music and deals with pertinent coming of age themes. Even for high school though, Sandy is a terrible girlfriend. As school is getting ready to start in the fall, let’s take a look at some of the shining examples of women who would have been great to date in high school. This list works best if you put “Don’t You (Forget About Me)” by Simple Minds on repeat while reading it.

10. Bailey Pickett ( Suite Life on Deck )


If possible, there is almost too much to love about the character Bailey Pickett. She is an unbelievably smart and attractive girl from the sticks (the fictional Kettlecorn, Kansas). She can rope cows and do every 'man activity' better than most men. As a matter of fact, she snuck on to the Tipton pretending to be a guy. She can also sing, dance and perform scientific experiments. The only potential drawback to Bailey is that she might honestly be somewhat intimidating. We think we could have handled it in secondary school though.

9. Cat Valentine ( Victorious )

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Let's face it. If you were a student at Hollywood Arts, there is almost a 98% chance that Cat Valentine would not be any type of stable relationship. Cat, quite frankly, probably has serious mental problems. On the flip side, it is high school. She is also an incredibly hot and talented free spirit. This is exactly the type of girl you would tell fond stories about for decades to come. This would also be sometime after she tried locking you in an adult sized birdcage and you ran away screaming from her.

8. Mikaela Banes ( Transformers )

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One of the great things about high school is it allows you to make incredibly terrible life decisions that will make you a wiser and happier man down the road. If you are a relatively happy suburbanite, the honest chances of having a stable lifelong relationship with the incredibly sexy but emotionally and psychologically scarred daughter of an ex-con are probably not good. But we are here to say, "Who cares? It's high school. You can't learn if you don't live." Of course, you are going to regret it. High school is also about building memories that will last a lifetime. A grease monkey who makes you sweaty definitely qualifies.

7. Rusty ( Footloose 1984 )


Undeniably, there is an allure to the Preacher's daughter gone bad. However, why deal with the baggage train that is Ariel? Rusty will still go dancing. She will still tie on a few. She is a country gal who is comfortable with who she is. When the situation absolutely calls for it, Rusty will scream at you an order to beat up a guy until he can't stand up. There is just nothing not to love.

6. Lorraine Baines ( Back To The Future )

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The best thing about Lorraine Baines is her basic understanding of maintaining appearances. Lorraine will absolutely be the girl to go out and party with you. She will drink. She will have a good time. She will get in the back seat of your car with the proper provocation. After Friday night, Lorraine will also go to church and clean up Sunday dinner with your mom. Lorraine understood how to cut loose like a kid as well as behave as an adult. It's little wonder guys were willing to break the barriers of physics to get with her.

5. Ali Mills ( The Karate Kid )

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Let's review. Ali Mills is not a "keeper." She can be won by right of combat and her primary motivation is upsetting her rich parents. Ali will leave you for the linebacker from UCLA. She also dated a guy who was perfectly willing to organize a gang for the sole purpose of doing you permanent bodily harm. However, for the brief period in which her charms are bestowed up you, you can get the rare confidence and sense of accomplishment that can fuel you through more healthy relationships. For the record, a Okinawan dancer won in the right of combat is not exactly a "healthy relationship" either.

4. Maria ( West Side Story )

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On the severe downside, you might not survive the experience. On the upside, Maria will pull out a gun and threaten to shoot up two gangs to honor your memory. A few different turns in the plot and you would never need another woman in your entire life. Granted, Thanksgiving dinner might not be the most ideal for a few years. On the other hand, don't families always come together over the grandkids?

3. Joanne ‘Jo’ Polniaczek (The Facts of Life)

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The big debate in the 1980s was Blair Warner versus Jo. Jo was a biker chick that went to a prep school. Blair Warner was a catty socialite destined for a lifetime of sleeping pills. Jo was a lot of fun and could fix a broken car. Blair was a sure road to bankruptcy court before you turned 18. There is a possibility that Blair would look better naked. There is an equal possibility that Jo would not only let you have a Playboy subscription, she would ask to read the articles.

2. Topanga Lawrence ( Boy Meets World )


For the record, high school was a wonderful time to have the last name Savage. Topanga was the strange child of two hippies who grew into a hard-working overachiever. When her hippie parents moved away, she stayed in Philadelphia out of love. She gave up the Ivy League to be with her man. Topanga allowed her heart to rule over her head and won all of ours in the process.

1. Winnie Cooper ( The Wonder Years )

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Gwendolyn "Winnie" Cooper stands as the ultimate high school girlfriend. As she grew up with neighborhood boy Kevin Arnold, they grew together and eventually grew apart. Winnie was there to teach the lessons that were necessary in childhood. When she became an adult, her life took a different path. She was smart enough to realize the difference. Sometimes, the best lesson of high school is growing enough to know when to leave it all behind.