People Do Cringeworthy Things in Their First Relationships
Illustrations by Brandon Celi

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Sex

People Do Cringeworthy Things in Their First Relationships

In six words.

Being in love requires vulnerability. That’s what makes it so scary and painful to give your heart away. And back when you first started dating and hadn’t experienced heartbreak yet, you likely leapt into your relationship with an open heart. As a result, almost everyone does something silly that they look back on and wince; truly cringeworthy moments send a chill down your spine when you think back on them.

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First relationships often involve messy emotional outbursts, embarrassing slips of the tongue, and other assorted adolescent fuckups. Everyone's got a story. We asked our friends and co-workers about their's. Here they are, in six words.

“Cried when he turned down sex.” - Lauren, 31

"Tried not to hate his mom." - Meredith, 26

"Performed duet of our love song." - Michael, 33

“Went to church on a Saturday.” - Justine, 22

“I tried to look more emo.” - Morgan, 19

"Broke up with her over AIM." - Matt, 30

"Puked in his bed, blamed him." - Lauren, 26

“Sang Blink-182 outside the window.” - Quinn, 23

“Tattooed his name on my breast.” - Noel, 31

"Commuted from Staten Island to Harlem." - Anna, 23

“Making out, whispered her sister's name.” - Leo, 37

“Slept with his best friend. Oops.” - Margo, 28

“Told parents I would marry him.” - Jenna, 30

“Threw love poems at him, literally.” - Sam, 26

“Tattooed initials after we broke up.” - Jason, 34

“I changed from scene to emo.” - Chantae, 27

“Carved her name into a tree.” - Bobby, 30

“Promised each other we’d remain virgins.” - Kelsey, 29

“For sale, riding crop, gently used.” - Jess, 34

“Brought best friends on our dates.” - Chloe, 30

“Burped into his mouth while kissing.” - Beth, 32

“Made him to lick my armpit.” - Lily, 23

“Got in spats at the mall.” - Rachael, 37

"Didn't date anyone else for years." - Beckett, 25

“Apparently his parents heard us fucking.” - Jennie, 34

“Smashed his cellphone during a fight.” - Lynn, 29

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“Begged him to take me back.” - Annie, 36

“Got matching tattoos on our ankles.” - Derek, 32

“Anniversary dinner. Left wallet at home.” - Marc, 37

“I said her mom was hot.” - Ian, 33

“Confessed my love on first date.” - Katie, 25

“Outside her house drunk and crying.” - Dale, 31

“Left long ass voicemail messages.” - Tyler, 32

“Lied about being in the Army.” - Billy, 33

“He tried to kiss; offered handshake.” - Pete, 35

“Pressured him about marriage and babies.” - Liz, 28

“We banged in my parent’s bed.” - Pearl, 32

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