The Problem With Going On Dates For The Free Food

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For those of us who are dating for the old-fashioned reason of trying to get to know someone, a transactional approach is deeply damaging, says Emily Heist Moss.

“I’ve got a pretty face and a pretty extensive Urban Spoon wish list…We all know that getting what you want in life can be tough, which is why I’ve decided to let someone else finance my dreams. My dream? To eat in pretty restaurants without costing me a penny. You had me at elk tartare, lost me at chin strop. Follow me to learn who I screw over, bang and love as I navigate Toronto’s diners, drive-ins and dives.” ~ Erin Wotherspoon, a 24-year-old with a Tumblr called “Restaurant Tips from a Serial Dater.”

Yikes. You have to give her credit, I suppose, for the sheer chutzpah it takes to post her manipulative plans on the Web with such transparent delight and joie de vivre. But really? This is what she wants to be famous for? People have become famous with less clever gimmicks, and Internet fame might as well be an Abercrombie sweatshirt in 1999 for how it’s coveted by Millennials, but her premise just seems so…lazy. And boring!

Some commenters have already started with the namecalling (use your imagination), while others have been defending Wotherspoon as only a more extreme version of the average woman on the dating scene. Is she a money-grubbing, gold-digging pseudo-prostitute? Or a savvy businesswoman wielding her assets to the best of her ability? Can she be both?

The commenters aren’t wrong: Wotherspoon’s strategy is more explicit and more public, but it’s not markedly different from attitudes I’ve heard many a dating lady express. I’ve watched friends and acquaintances waffle over a so-so prospective date and ultimately decided to attend because, “Hey, free dinner, right?” I’ve heard guy friends worry about bankrupting themselves due to an especially busy stretch of OkCupid dates. Is there a difference between transactional dating—which many serial daters nonchalantly participate in—and Transactional Dating—the codified system of trade-offs that Wotherspoon espouses?

The idea of transactional dating is essentially timeless, given that we are just now beginning, slowly, to crawl out of the muck of a dowry based system—two cows for the first crack at her hymen? Deal! It’s not a far stretch from buying brides from their fathers to a status quo in which men fork over cash for the pleasure of female company. It’s money (or elk tartare, if you’re Wotherspoon) for sex, or the slim possibility of sex, no matter how you slice it.

What’s so wrong with that? We’re all consenting adults; if he wants to pay for tiny plates of swanky food and she wants to let him, why do I care? I don’t, not for Wotherspoon specifically, or any other particular duo. As with most things we discuss on this site, it’s not about the individual cases. I couldn’t care less how a given couple operates or how a date goes down. In aggregate, as an organizational structure for how the genders relate, I care a whole lot. Wotherspoon’s Tumblr is just one example of how the rules of modern dating are still structured in ways that undermine both men and women.

Transactional dating is based on assumptions about what the genders want out of a date. It assumes that women want to be provided for, and that men want to be providers. It assumes that women are valued for how they look, and that men will pay to be seen with a pretty girl. It assumes, at least in some cases, that women will decide whether or not to have sex with someone based on how much money he has plunked down. I wish I could say these assumptions were universally false, but that would be laughably naïve. I will say this; these don’t do any of us any favors when we’re trying to forge real connections.

For those of us who are dating for the old-fashioned reason of trying to get to know someone enough to decide if we’d like to spend more time together, a transactional approach is deeply damaging. Even when both people want a date to be based on sincerity and an egalitarian spirit, the effects of the Wotherspoon methodology are hard to avoid. The expecations that are so pervasive that we have to actively combat them to keep our date grounded in equality.

How many dates have I been on where I had to explain that I really prefer to split the bill (or take turns if we’ve been going out for a bit), and that it doesn’t indicate friend-zoning or lack of respect? Almost all of them. I can’t blame men for not knowing how seriously to take my preferences because women in their pasts have used the same language to indicate exactly the opposite.

The conventions are so hardwired into the system that we can’t trust each other to be honest. Overriding those conventions, even when we both want to, now requires all this extra effort and potentially awkward conversation. For me personally, it’s worth it to mould dates into the experience I want them to be, but I can’t blame others for shrugging and going with the flow.

I have no doubt that Wotherspoon’s plan will pan out. There are certainly enough men who don’t mind paying for a pretty date, even if they know that she’s only in it for the $19 glass of wine. She’ll make the system work for her and enjoy some really spectacular food while she’s doing it. For the sake of the rest of us, though, I wish that transactional dating could go the way of the brideprice.

Role/Reboot regular contributor Emily Heist Moss is a New Englander in love with Chicago, where she works in a tech start-up. She blogs every day about gender, media, politics and sex at Rosie Says, and has written for Jezebel, The Frisky, The Huffington Post and The Good Men Project. Find her on Facebook and Twitter.

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