Valentine’s Day Disasters: The Tale Of Paul, An OkCupid Creep Who Wore Ostrich

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For this Valentine’s Day, we want you to share your weirdest, worst and most WTF moments from V’days past. We’ll post them through Valentine’s Day, then have readers vote on whose story is the best (well, best-worst) and the winner will receive an amazing Pacifica prize pack. For contest guidelines and details on the prize, click here! You can read all the entries here.

About a week or so before Valentine’s Day, I found “Paul.” He was the first man discharged to me from the bloated bowels of OKCupid. Paul worked as a mid-level manager for a legal consulting firm downtown and enjoyed dove hunting, Malcolm Gladwell and his Lexus. In addition to this, he informed me in a pre-date message that he would be picking me up “in the Lex” and take me to dinner at a chi-chi restaurant. He then messaged me the day of our date (Valentine’s Day, no less) to lay out an e-neg: since he didn’t know that I was “worth it” yet, we’d be going to an IHOP. Winky face. Why I didn’t cancel, I still don’t know. The pressure of having a Valentine’s date? Anyway…

During dinner, he spoke extensively about his collection of custom-made exotic skin cowboy boots, insisting that I feel the texture of the pair he had on (ostrich). He then dove into work talk, repeatedly referring to his staff as “peons” and “minions” unironically, and letting me know that while he OBVIOUSLY had to keep his useless underlings around him at all times, he could make them stop their work and wait in a conference room if a special lady (hint) happened to stop by for a midday quickie on his desk. Cue an intense stare.

Having veered the conversation back to something less horrifying, he again began talking about his boot. Then, tragedy struck: I took a sip of my water and accidentally inhaled it. I started to cough pretty forcefully and did my best to minimize the interruption, covering my mouth and trying to shrink down into my chair and away from the restaurant’s cumulative side-eye. Having caught my breath a bit, I look up to see Annoyed Face. I gesture to him to continue his story, flashing an apologetic smile. Maintaining perfect Annoyed Face, he loudly says, “NO. I DON’T APPRECIATE YOU DOMINEERING THE CONVERSATION. I’LL JUST WAIT UNTIL YOU’RE DONE.” The restaurant suddenly became very quiet save for the noise of pink glittery garlands brushing together in the breeze from a heating vent.

At least he paid. He then insisted on walking me to my car, which was parked under a streetlight, so there was a cloud of crickets and moths buzzing into my hair and down my collar as he aggressively tried to kiss me, landing a damp tongue on my cheek while an insect crawled along my scalp.

He texted me later to say that I earned a dinner at the fancy restaurant. I replied that I wasn’t interested. He texted back with a long, detailed story of how he wanted to take me dove hunting and fuck me against a tree. Much narrative was given to the act, force, and profundity of his hypothetical ejaculation.

On the bright side, the next guy I went out with from OKC was a prize gentleman, and we’re still happily together over a year later. There is hope!

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    • Kaitlin Reilly

      Sounds like a crazy person… I hope he doesn’t still have an account!
      It’s horror stories like this that make me wary about online dating, though, to be fair, I’m sure the horrible dates are talked about more frequently than the nice, normal dates people go out on. I’m glad the next guy you met on the site was great!

      • Bunny Lucia

        I’ll tell you a nice little story!
        I met a guy on OkCupid, we went on a date at a bowling alley. Had the most fun I have ever had in years, we’d yell things out like “METAL!” or “GRUNGE!” or if we got a gutter ball we’d be like “Soft grunge!” Then we went to a nickel arcade, played racing games, then I went home.

        There’s a lot more good than bad when you’re online dating, but the bad is sometimes so extraordinarily bizarre that you can’t help but talk about it.

      • Kaitlin Reilly

        Exactly! Like with any terrible dating story, you can’t help but share it. I think that it’s basically just weeding out the people who are on the site for the wrong reasons… but that’s sort of like life, too, so it’s not that different. Glad to hear you had a good experience!

    • Lindsey Conklin

      Wow. This sounds absolutely horrible. At least it makes for a good story? haha

    • SexyJewsus

      What do women expect when they go out with a guy who kills doves for fun, and then has the arrogance to say that they may not be “worth” taking to a decent restaurant before even meeting?? Many women are getting what they deserve by even agreeing to give a-holes like that a chance.

      • bubba

        hey douche….dove hunting is fun.

    • Marilyn Shelton

      I once went out with a guy who sipped Vodka straight from the bottle as we went ice skating then went home on the bus because he had a DUI.

    • Guest

      Ostrich boots??…did you go out with Lieutenant Dangle???

    • Mars

      Ostrich boots??…did you go out with Lieutenant Dangle???

      • dlillroy2012

        New boot goofin

    • Farty Fartsalot

      Seriously, what ever happened to dating in the real world? It’s much easier & saves you some passive-aggression

      • thatgirl

        um, IMO, it definitely does NOT save you any passive-aggression. people can also be asshats in person.

      • Farty Fartsalot

        So what? Atleast you get rejected right off the bat. You get over it pretty quickly.

    • Moondancerr

      I agree, if your THAT STUPID to tolerate the crap talk and behavior before hand…WHAT DO YOU EXPECT? for all you women out there…. YA NEED TO STOP THEE ABUSE NOW …STOP TOLERATING SHABBY TREATMENT TO YOURSELF AND WALK OUT!!!! It’s that simple. The VERY 1st ignorant, disrespectful or inaproppriate comment made you need to CHECK his ass and get up and LEAVE!! He said stop the conference for a quickie on his desk AND YOU COULDN’T TELL HE WAS A DUCHE BAG? C’MON NOW

    • Moondancerr


    • dlillroy2012

      “At least he paid” moving feminism forward one sellout at a time.