Top Ten Worst “First Times”


“The First Time” has been romanticized by music, television, and especially movies. The truth is that “The First Time” is often awkward, painful, and messy, and it isn’t usually with a soul mate or a Victoria’s Secret model. This Top Ten List is a tribute to all the first times that weren’t sexy, earth-shattering, or even fun.


#10 - The 40 Year Old Virgin

While it may not have been the first roll in the hay for Trish (Catherine Keener), Andy (Steve Carell) had not indulged in the joys of the flesh until his wedding night. From the look on Trish’s face, Andy’s first time was perhaps a bit…underwhelming. He quickly makes up for it, though, and leaves Trish panting and red-faced after only his second time around. It was a long road to Andy’s first time, but he seems to be a fast learner.


#9 - When Harry Met Sally

Both Harry (Billy Crystal) and Sally (Meg Ryan) were sexual veterans, but despite being best friends, they had never seriously considered each other romantically. Sally hears that her commitment-phobic ex-boyfriend is marrying someone else, and distraught, she calls Harry. Half a box of Kleenex later, they find themselves in bed together. Their discomfort afterwards is palpable, and their one night stand destroys their friendship. Fortunately, there is a happy ending for Harry and Sally, but until then, their first-time is a complete disaster.


#8 - Juno

On the day that Paulie Bleeker (Michael Cera) lost his virginity, The Blair Witch Project was on TV and Juno (Ellen Page) decided that she would rather have sex instead. Knowing that The Blair Witch Project was a close second to having sex with him was bad enough for Paulie, but on top of that, Juno winds up preggers, drinking gallons of Sunny Delight on her front lawn so she can take yet another home pregnancy exam.


#7 - Saved!

In Saved!, Mary (Jena Malone) and Dean (Chad Faust) lose their virginity trying to do God’s will. Dean suspects that he might be gay, and Mary decides that she must try to turn Dean straight by sacrificing her virginity. Like Juno, Mary ends up pregnant, and Dean is shipped off to a Christian camp specializing in “curing” homosexuality.


#6 - Sixteen Candles

In Sixteen Candles, Anthony Michael Hall’s character, known only as “The Geek,” gets the perfect conditions for his first time. He has a classic car with a huge backseat and a prom queen who isn’t too drunk to say no but just drunk enough to say yes. Nothing could go wrong…except waking up the next morning and not remembering any of it. Hall’s geek character has to ask the prom queen, the woman of his adolescent fantasies, if their night of passion was good. Oh buddy…better luck next time.


#5 - An Education

Jenny (Carey Mulligan), like Hall in Sixteen Candles, has the perfect setting for her first time. Her older boyfriend David (Peter Sarsgaard) has taken her to Paris for her 17th birthday, and they are all alone with no chaperone. David botches their first attempt by suggesting that they get things started with a banana, to which Jenny indignantly says that she will not lose her virginity to a fruit. When they finally do the deed, Jenny seems disappointed to say the least. She quietly remarks, “All that poetry and all those songs, about something that lasts no time at all.” Ouch.


#4 - Forgetting Sarah Marshall

In Forgetting Sarah Marshall, Peter (Jason Segel) meets Darald (Jack McBrayer from 30 Rock) and Wyoma (Maria Thayer), a strictly religious couple on their honeymoon. Unfortunately, due to their lack of experience in bed, neither Darald nor Wyoma are having any fun. Fortunately, thanks to rocker Aldous Snow (Russell Brand), Darald learns how to please his new wife, and their honeymoon ends with a bang.


#3 - Big

Big wins the prize for one of the most perverted first-time scenes on film. Josh (Tom Hanks) might look old and Susan (Elizabeth Perkins) might be hot, but this scene is wrong for so many reasons. It is to writers Gary Ross and Anne Spielberg as well as director Penny Marshall’s credit that Josh and Susan sleeping together does not bring down the whole movie and that Big is still considered a modern day classic.


#2 - Teeth

For Dawn (Jess Weixler) and Tobey (Hale Appleman) in the indie horror film Teeth, their first time was terrible for completely different reasons. Dawn realizes that she has teeth in a rather unfortunate part of her body, and Tobey also discovers this as well, though a little too late to save a certain part of his anatomy. This film should be shown in high school classrooms instead of those slideshows displaying the effects of sexually transmitted illnesses. I guarantee that this film will scare the boys so much that they won’t even consider pressuring their girlfriends.


#1 - American Pie

No list would be complete without Jim Levenstein (Jason Biggs), the unlucky protagonist of the American Pie trilogy. In the original film, Jim and his friends are trying to lose their virginity by prom night. Jim’s first time ends up being with a fresh-baked warm apple pie, and to make things more embarrassing, he is caught in the act by his dad (Eugene Levy). Jim’s dad is understanding and assures Jim, “We’ll just tell your mother that we ate it all.” Classic.

Rachel Kolb • Staff Writer

I love movies, writing, and breaking into song in public. You can follow me on Twitter @rachelekolb or check out more of my work at http://rachelekolb.wordpress.com.


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