Skip To Content

    17 Of The Most Painfully Awkward And Embarrassing Teen Drama Moments In The History Of TV

    "I got kissed...and I shoplifted!"

    1. First, when Deb ran into Lucas and Brooke while they were buying condoms and whipped cream on One Tree Hill.

    The WB

    2. When Naomi dressed up as a blue alien from Avatar to impress Max, not realizing that nobody else was going to wear a costume on 90210.

    The CW / Everett

    3. When Otis tried to discreetly buy the morning after pill for Ruby and the cashier couldn't hear him on Sex Education.

    Otis asks for the morning after pill, the cashier, "what? I can't hear you! the morning after pill?!"
    Netflix

    4. When Stan tried to roll down his window to smoothly ask Syd if she wanted a ride to school, but it took a million years for the window to work on I Am Not Okay with This.

    Netflix

    5. When Manny walked in on J.T. using a penis pump on Degrassi: The Next Generation.

    CTV

    6. When Rory shoplifted the cornstarch after Dean kissed her for the first time on Gilmore Girls.

    Dean kisses Rory and she says "thank you" and runs out of the store
    The WB

    Rory Gilmore truly peaked when she said, "I got kissed...and I shoplifted!"

    7. When Ben overheard Devi's mom telling her to be nice to him through the air vent on Never Have I Ever.

    Devi's mom says Ben is going through a hard time and had "one of the nastiest pimples" she had ever seen in her career
    Netflix

    8. When Rachel fell in love with Mr. Schue after they sang a duet of "Endless Love" on Glee.

    FOX

    In Rachel's defense, who sings this song with their student?!

    9. When Tiny was trying to be genuinely helpful and bring Shay pads, but gave her two huge boxes of them in the middle of class on Degrassi: Next Class.

    Netflix

    10. When Seth and Summer shared an awkward first time on The O.C.

    Seth says he's going to go and Summer says she is too, Seth awkwardly reminds her she lives there
    FOX

    This was probably the most realistic depiction of losing your virginity I've ever seen on a teen drama, though.

    11. When Pudge puked all over Lara on their first date on Looking for Alaska.

    Hulu

    12. When Grace started a campaign called "Just Say Me" to encourage her friends to masturbate instead of having sex, and everyone acted like they had literally never heard of it before on The Secret Life of the American Teenager.

    Amy asks why nobody ever told her about masturbation at band camp and Ashley asks why someone would even need to tell her about it
    Freeform

    Honestly, I'm convinced this whole show was just a fever dream.

    13. When Lola brought a vibrator to school thinking it was just a funny keychain on Degrassi: Next Class.

    Lola holding a vibrator: "I know right? And it buzzes!"
    Netflix

    14. When Betty's mom found her cabaret wig on Riverdale.

    Chic tells Alice Betty uses the wig when she has sex with Jughead
    The CW

    15. When Marissa said "I love you" to Ryan and he responded in the most awkward way possible on The O.C.

    Marissa: "I love you," Ryan: "Thank you"
    FOX

    16. When Blair got really drunk and got arrested on Gossip Girl.

    The CW

    We've all been there, Blair.

    17. And finally, when Finn sang "(You're Having) My Baby" to Quinn in front of her parents on Glee.

    FOX

    "Don't. Finn, seriously, DON'T."

    TV and Movies

    Get all the best moments in pop culture & entertainment delivered to your inbox.

    Newsletter signup form