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That moment the relationship got complicated

Shotgunning weed smoke into my girlfriend's mother's mouth and more brief stories of dating difficulties.


  • Katie Carey

Things got complicated when my girlfriend's mother made me shotgun weed smoke into her mouth.

The horror is incremental. "Of course you can step outside with us" turns into "Oh, you don't mind us smoking?" turns into "That sucks about your lungs, sorry you can't inhale" turns into "Sure, what favor?"

What favor, indeed.

I inhale—half from the joint I was hitting, half from the shock. She opens her mouth, a gaping, middle-aged maw lined with uniformly bleached gravestones, each one marking the demise of my innocence. Paralyzed by the abyss, my lips hover centimeters from hers, like a skittish bee over a dry, chapped flower. I exhale. The smoke leaks from my lungs, and with it my dignity. Broken, I make eye contact with my girlfriend—her daughter—who stares back, smiling.

Later that night, my girlfriend thanks me for being such a good host to her mother. We date for one more year.

  • Katie Carey

Things got complicated when I found out my summer crush was a billionaire.

How to avoid getting cursed out by a French heiress in the middle of a Manhattan Starbucks:

Don't perform at Maine's only improv comedy club.

Don't talk to the pretty girl after the show.

Don't notice her accent.

Don't meet her the next night.

Don't walk through a forest to a clear black lake underneath the Milky Way.

Don't think about how she's catching a plane in six hours.

Don't find out she's the heiress to a Mexican silver-mine fortune.

Don't ask her about her home in the south of France or her great-uncle who raised gazelles in his bathtub.

Don't spend the next day snooping online to see if you were catfished only to find out you weren't.

Don't talk to her online from time to time.

Don't agree to meet up with her in New York City months later.

Don't tell her, "I think I'm in love with someone else."

Don't expect to see her ever again.

  • Katie Carey

Things got complicated when I made my girlfriend's OCD go ham.

My college girlfriend was struggling with OCD—specifically, all-consuming thoughts of her loved ones dying. I did my best to encourage her to get help, and after a few months she agreed to see a therapist.

Her first session went great—right up to the point when she turned on her phone outside the doctor's office and discovered the 14 sobbing voice mails I had left her in the past hour. You see, while she was dealing with paralyzing visions of the untimely demise of family and friends, I had gotten in a car accident and almost died.

She never went back to therapy.

  • Katie Carey

Things got complicated when my girlfriend brought home a pocket pussy.

My girlfriend Claire works for a cool hip company that often gets cool hip merch from other cool hip companies. Sometimes she gets to bring that merch home. Sometimes that merch is a Fleshlight.

For those unfamiliar, imagine a rubbery earthworm stuffed into a 64-ounce Big Gulp cup. Sound unsettling? It is!

"So," Claire asked, "what are you going to name it?"

After "the Harbinger of Your Sexual Obsolescence" was immediately shot down, we spitballed for a while trying to find the perfect name. "Lazy Susan." "The Goop Trooper." "Yoko Silicone-o." In the end, Claire got the final say: "Claire Two."

  • Katie Carey

Things got complicated when I overdid it on my hookup schematics.

Like many teenagers, I went to great lengths not to get caught engaging in carnal shenanigans. My most brilliant plan? Sixty-nining under my family's dining room table.

In this X-rated game of Don't Wake Daddy, the dining room was the farthest point from my parents' bedroom (not counting the unfinished basement, which was deemed too cold in preliminary testing). The table itself provided fantastic overhead cover, and its fold-down wings muffled slurping sounds while keeping my golden retriever from getting too sniffy.

As some of you will note, you can't 69 solo, so AT LEAST ONE OTHER PERSON THOUGHT THIS WAS A VIABLE IDEA.

Long story short, my parents never came downstairs, and now I have faraway thoughts during Thanksgiving dinner.

  • Katie Carey

Things got complicated when my relationship's best memory was a kidney stone.

When a relationship ends, it's easy to hate. To lay blame. To say, "You suck, you lied to me, and that time your mom made me shotgun weed smoke into her mouth was NOT COOL."

It's harder to forget the selflessness, the moments when someone truly cared for you. Loved you. Drove you to the hospital with a jug of your bloody urine in her lap as you screamed deliriously in the backseat in a futile attempt at penile Lamaze. I imagine this is due to the fact that bloody urine, much like baptismal water or writing a single Facebook post condemning Rahm after not bothering to vote last year, has the unique ability of absolving people of their wrongdoing.

Point is, sometimes the one good thing ends up being a kidney stone. v

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