When I first moved from Chicago to ski bum in Telluride, CO, I worked as a snowmaker. During a shift change, a pal of mine began to bark the dating cliché, worn especially thin in mountain towns: There are no women here. Before he could bemoan his point too long, our boss shot back, “It’s not that there aren’t any women in Telluride. There’s just a ton of dudes without any game.” And what is true in Telluride is true in Chicago is true everywhere. If there is an issue with your dating life, it has little to do with the person you’re hollerin’ at and nearly everything to do with what and how you’re hollerin’.

To be clear, I am speaking directly to men. (Mansplaining dating advice to women is a bad idea for several million reasons, not least of which is the fact that, like everything else mansplained to women, they already have it figured out.) And I can only speak to my dating experience as a straight white man—experience meaning a rollercoaster that until very recently, after extensive work with a therapist, resembled the path of a drunken, peg-legged pirate wearing two eye patches. Along the bumpy ride I’ve only seen more and more evidence to support one truth: Striking out is due to your bad batting. That is to say, you are bad at dating.

Yes, “dating is hard.” It’s an easy first retort, which translates to: “Man, I can’t find a woman who wants to listen to me talk about myself and nothing but myself.” The other day, I joked about this to my cousin-in-law Graciela, who snapped eagerly back about just how obvious it is when she’s speaking to a man, “and the person you’re talking to is preparing his response rather than actually listening.” No surprise, she points out, “the response usually has everything to do with him and nothing to do with you. My advice is to actually listen, because we can tell when you aren’t.”

Bored man listening her friend talking in a coffee

And the other thing you don’t need to talk about is how extra hard is to be dating during a pandemic. Since the onset of COVID-19, dating apps like Tinder and Bumble reported a sizable increase in users, length of time on profiles, and conversation. Zoom and FaceTime usage rate have ballooned with e-dates. And even in a pandemic, people are figuring out how to get physical, which is why New York City public health officials created a Safer Sex and COVID-19 fact sheet. It includes ideas like masks during sex, ventilated spaces for group sex, and holes in walls or barriers to avoiding face-to-face contact. Yes, that’s right: The NYC government suggested pandemic glory holes and open-air orgies. Suffice to say, people have been figuring out how to corona-date and finding success, so what’s your excuse? Perhaps it’s time to learn from those who’ve been subjected to crappy dating.

attractive woman seriously listening

Try To See This From Her Perspective

My friend Elizabeth has been on what she describes as a 20-way tie for worst possible date ever. The common denominator for each was a lack of emotional regulation. “I’m talking angry outbursts, meltdowns, and sex requests at the top of a first date,” she told me. Yikes. My cousin Claire told me that she once met a guy for a drink who had another gal with him when she arrived, which is when he suggested they all have a threesome. She refused and left. That date, by the way, was not her worst date ever. Double yikes.

Along with sexually explicit dumbassery, how else are guys floundering in the dating pool? Elizabeth told me that while being spontaneous is a good thing, it’s only acceptable in limited amounts. “Having no plan for any date can be frustrating and unnecessarily stressful,” she says. My sister Kitty thinks splitting the check is a major no-no. “I’m an independent woman and identify as a feminist, but I still like to be treated to dinner,” Kitty says. “Do a sneaky move and pick up the bill on the way back from the bathroom.” Claire agrees: “Chivalry is not dead,” she says. “Treating someone like they matter to you, in ways big and small, is pretty much the most attractive quality a person can have.”

dating at the club
Just put the tab on that card when she’s not looking. Shutterstock

Claire also points to toxic masculinity as a date destroyer, specifically the idea that vulnerability and showing emotions is a turnoff. “We somehow have all bought into this idea that men have to be ‘strong,’” Claire says. “I think for a lot of guys that translates into projecting this phony-bro persona in a misguided attempt to impress women. But, true strength really lies in being able to open up, speak from the heart, and show who you really are.” Showing his emotional side is what first attracted Claire to her future husband. The night they met, the guy recited a goddamn Shakespearean sonnet for crying out loud. (“It was actually less cheesy in context than it sounds now,” Claire notes.)

Some Simple Solutions

So, what else works? “He called to ask me out on our first date,” my sister said of her husband. It should be noted that Kitty told their mutual friend that if he texted rather than reach out more personally, she would Heisman his ass. “My guy often tries to meet my wants and needs before I articulate them to him,” Elizabeth explains. “Before him, I had never dated a guy who would, say, notice that my wallet was fraying and buy me a new one, or take an offhand comment about kayaking and research a date around that activity. So, basically, it was seeing and hearing me, and then proactively trying to improve our relationship.” All three note that effort, listening, and giving a shit should not seem like novel, shocking ideas, but guys don’t always see the simple and obvious.

dating douchebag
Remember: No mentions of PRs, WODs, or wads. Shutterstock

Here is the hard truth, dudes. You are not helping your cause. Toddler-ass Chads masquerading as men far too often use dates as a means of self-congratulatory pomp and ego stroking, like some Axe Body Spray-soaked, tank top-wearing lovechild of Narcissus and Dorian Grey. If you want to spend time chatting about your PR on Strava this week (and you know how I feel about Strava), or the sick time you and your bros had at last year’s Tough Mudder, how expensive your road bike was, how hard you crushed today’s WOD (don’t talk to anyone about your wod or wad, please), or any other cool-guy exploits, do it with the man in the mirror. He’s the only one interested. Word barfing your adventures and achievements in an attempt to prove your coolness does nothing but fly an enormous, unfurling flag of self-indulgent dweebery. And I bet the gal across from you is actually super cool. You should find out.

And for the love of god, stop it with the dick pics, you degenerates. “No girl wants to see a photo of your penis. Trust me.” Said by Claire, and legitimately every woman ever.

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