Guest Post: The Dangers of Dating While Freelancing

Meet Jessica Leigh, today’s guest-poster! Like me, she is pursuing that miserable beast known as “online dating.” Except instead of the reasonably safe waters of Chicago, Jessica is swimming with the sharks in New York City. What happens when an aspiring freelancer dates other aspiring freelancers?

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New York is lousy with freelance writers. Surely this is not a revelation to anyone who has ever seen a film or TV show about twenty- or thirty-somethings’ stumbles and sexual exploits in the Big City. (My interior monologue is still read in Carrie Bradshaw’s smirking cadence.) I’ve always known that lots of wordsmiths flock to New York to lurk in coffee shops and write snarky reviews or thoughtful long-form exposes, but the size of this demographic didn’t hit me until I became unemployed and joined their ranks full-time.

I’m on the prowl for another job, but in-between firing off pitches and resumes and trolling boutiques and restaurants looking for work, I sit in coffee shops and creep on my writing competition. I’m generally mild-mannered, empathetic, and non-confrontational. However, crankiness spurred on by my non-existent paychecks, air-conditioning, and promising prospects has brought out the worst in me. My warm-weather, no-income alter ego is ferocious. Cute guy with the thick specs and tousled locks, hunched over his laptop and squinting in concentration? Better stop fantasizing about his eyes behind those glasses and start thinking of him as The Enemy. There are dwindling numbers of 500-word columns about arts and culture, and this island isn’t big enough for the both of us.

This problem is further complicated by the fact that I’m simultaneously trying to break into writing and the dating scene. Suffice to say, I find myself on lots of dates with fellow aspiring freelancers, which means that between bites of budget-friendly food, we dig for dirt about writing opportunities. When I find myself on dates with fellow writers, I sometimes discuss pieces I’ve written. I am wont to wax poetic about the muffins I reviewed for a local site, or prattle self-consciously about articles past.

Mutual sharing usually leads to cheers and high-fives: it’s pretty fun to write pithy pieces, and even more fun to rehash the hours you spent agonizing over alliterative puns or double-fisting salty snacks while reading scathing comments on your blog and wondering if you’re the Worst Writer Ever. Generally, these conversations are hilarious, fun, and lead to another round of pity-party drinks as we strategize about getting gigs. Yesterday, though, this mutual disclosure turned daunting when it occurred to me for the first time that (gulp!) I could become an anecdote or character in one of my dates’ articles or stories.

Mid-way through my iced chai, I learned that my date authors a sex and dating column for a highly-read women’s magazine (“I know, it sounds kind of stupid,” he allowed. “How many times do I need to reiterate, ‘Just suck his balls?!’”). I immediately felt uncomfortable. Would he describe our date in his column? Would I be identified as “Girl Who Visibly Squirmed When I Said the Word “Balls” on Our First Date?” Did he invite me out because he really found me intriguing, or because he needed to conduct an informal survey for an upcoming column (maybe something along the lines of: “Do Dates Find It Arousing When You Casually Mention That You Broadcast Your Sex Life to 10 Million Readers?”)? I’m a longtime reader of my date’s column—weirdly, even though we haven’t hooked up, he has shaped a fair share of my sexual technique. Does the fact that I—and my partners—have benefited from his recounting his tales of (to put it crassly) tail mean that I should stop panicking about becoming one such story? I don’t think so. One of my previous boyfriends writes short stories, and I was always comforted when his characters evinced neuroses that where reassuringly different from my own. I don’t like unexpected cameos between the sheets of someone’s bed or pages of someone’s magazine. There won’t be a second date. I want to keep my sex life in my own bedroom—not on millions of other ladies’ nightstands.

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Since the writing of this post, Jessica is happy to have disabled her OkCupid profile. Now she spends her time stalking her neighbors’ stoops to snap shots for her blog, where she geeks out about plants and people who grow them.

Related Post: Another recent guest post about Cosmo, sexual honesty and kink.

Related Post: Best online messages to date.


Filed under Gender, Guest Posts, Really Good Writing by Other People, Sex

4 responses to “Guest Post: The Dangers of Dating While Freelancing

  1. Pingback: Happy Birthday? | rosiesaysblog

  2. Pingback: I Think I’m Doing OkCupid Wrong | rosiesaysblog

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