Bad With Men: Why Am I Only Going On First Dates?

Dana Norris is the founder and host of Story Club. She once went on 71 internet dates.

I decide to run some stats on my dating life.

Number of men I have dated so far: 21

Number of second dates: 4, or 19%

Number of third dates: 2, or 9.5%

Number of men I wanted to see again who did not want to see me again: 14, or 66%

I have a 66% failure rate at dating. And I’ve been trying really hard. I’ve been dating all kinds of dudes: short, tall, skinny, girthy, various hair colors and facial hair situations and ethnicities and employment statuses and fitness levels and educational backgrounds. And the majority of the time I walk away thinking, “I’d totally see him again,” while the dude walks away thinking, apparently, “Nah,” or, even worse, “Do I want a hot dog? What’s on TV?” 

I am not captivating anyone. 

I decide that the problem is me since I’m the one thing all these dates have in common. I try to figure out where I’m going wrong. Maybe I’m playing it too cool? I try to be nice while on dates and smile at the men and ask them questions, but I don’t really actively flirt with them. Maybe I’m making the mistake of talking to them, just talking to them, as though we are both normal human beings. But we are not normal human beings. We are people on a first Internet date and therefore we are commodities who are interviewing each other.

I imagine that these men are all dating as much as I am, if not more. I decide that I need to make myself more appealing out there on the dating market. Maybe I should wear more skirts? Or start touching these men lightly on their forearms? Do guys like that? Forearm touching?

I decide to clarify my goal: I am Internet dating because I want to find love. My goal isn’t to go on dozens of first dates—my goal is to find a partner to walk with me through life. I decide to stop being so passive and to actively start pursuing men online. 

I find one, named Alvin. He has a beard and an advanced degree and brown eyes that crinkle when he smiles. I message him, he writes back, I ask him if he wants to go out sometime, he says yes, and it is on. He can meet me downtown on a Wednesday evening in the short window between when my work ends and my evening grad school class begins. He wants to meet at a breakfast place near my school at 5pm which sounds crazy to me because why would that place be open at 5pm? But I’m not here to judge: I’m here to trick this stranger into loving me. 

I meet him outside of the breakfast place, which is, obviously, closed. Alvin is embarrassed. “Guess I should have looked that up online first, huh?” I laugh and tell him that it’s OK while also quietly judging him in my mind. He suggests that we walk up the road a bit, to a coffee shop he knows about that’s hidden deep within a medical building. I agree and as we walk he starts asking me questions about grad school and the class I’m taking. I tell him it’s a writing workshop. He asks if I wrote anything for class tonight and I say that I did. He asks me to tell him about what I wrote and I stall for time. Because the piece I wrote for class is a nonfiction essay about how, when I was 2 years old, I had the kind of dysentery that used to kill people on the Oregon Trail.

So I lie. I say that I wrote about a long late night car trip and it sounds incredibly boring even as I’m making it up and Alvin feigns a bit of interest and we thankfully move on.

We get to the coffee shop and sit down and Alvin starts telling me about himself. He has a very rumpled professor vibe about him and I’m digging it. He leans back in his chair and looks very casual and relaxed. He’s a psychological researcher, which is wholly fascinating to me. He tells me about his experiments and his career goals and I notice that, though he’s wearing a fairly neutral button-down shirt and brown slacks, he is also wearing bright red socks. That is awesome.

I decide right then that I very much want to go out with this guy again. But how do I convey that? I start to play with my hair because I read somewhere that this is what women do to unconsciously show that they’re interested, except I’m doing it consciously and it feels like I’m pawing at myself so I stop. I try to be funny and make him laugh, which he does, but then I think that maybe guys don’t like funny women so I stop being funny and instead laugh wildly at the few jokes he manages to eke out. My God this is difficult. 

It’s time for me to go to class and Alvin walks me to the front of the building. “I had a nice time,” he says. “Me too,” I say. And then I turn around and head inside to class.

My grad program is for adult students who work full-time and thankfully someone brought a few bottles of wine to class tonight. I still feel nervous about my date so I quickly drink down a glass of wine on an empty stomach, followed by another, followed by some pretzels, and then another. I’m telling other people in my class about my date, “He was cute! And he wore red socks! And he does experiments on monkeys I think, which could be a problem, but…red socks! Brown eyes! I want to see him again. Can I have some more wine?” Everyone agrees that it sounds like he’s definitely going to call me. 

Class ends and I head home. I sit on my couch and turn on the TV and I’m still feeling the wine and an idea starts to gnaw at me. I didn’t really flirt with Alvin. Not really. I didn’t touch him or tell him that I want to see him again and I certainly didn’t kiss him. I should have kissed him. Why didn’t I kiss him? Maybe I can tell him that I wanted to kiss him and that will make it like I kissed him. Yes. I should tell him right now. 

I write Alvin a text: “I should have kissed you tonight.” I stare at it for a moment, white and unsent, and I desperately want to delete it. But no—I am trying to date differently. I am trying to be active and to pursue men and to not be afraid to ask for the relationship that I want. I close my eyes, yell, “Fucking hell!” and hit “Send.”

Twenty minutes later he hasn’t responded and I am staring at my phone in agony, wondering how my life came to be such a wreck. But then my screen lights up and my phone buzzes. It’s a text! It’s him! 

I read it eagerly. It says, “Ha ha.”

So that’s not the text of a man who was smitten by me. Then the phone buzzes again: “I’m flattered. But I was really getting more of a friend vibe.” I am immediately crushed. I really liked that guy. I mean, I only spent two hours with him, but I liked him as much as you can like a guy after one two-hour date followed by a bottle of wine. 

Why isn’t this working? It’s not like I have unrealistic standards. I’m dating everyone I can and I’m trying to find something to like about every guy I go out with—no job? Who cares! Weird teeth? OK! Twenty-three years old? So was I, once! Libertarianism? Well, someone’s gotta be!—and yet the vast majority of these guys decide that they don’t want to date me. They’ll go on a first date with me and they’ll sit with me for hours, probably in the hopes that the evening will end in sex, but then the evening ends without sex and we go our separate ways and it’s like the date never happened. They aren’t actually interested. I have no idea how to get a guy to date me more than once, let alone sign up to be my boyfriend.

And now I’m wine crying, which is one of the worst kind of cries because it’s loud and it gives you a headache and when you wipe your face you realize you’ve been walking around with Merlot-stained lips all evening.

I calm myself down and put myself to bed. I sniffle into my pillow and try on some logic. Alvin doesn’t want to date me. This says nothing about me other than the plain fact that this particular man, Alvin, does not want to date me. It is not a comment on my overall appeal or a reflection of my likelihood of ever finding love again. And it may be true that so far 66% of the men I wanted to date again did not want to date me again. But each man is an independent variable and they don’t necessarily indicate a pattern.

Finding one person who I like who also likes me is taking longer than I thought it would, but that doesn’t necessarily mean that I’m failing. Maybe it just means that the search for love is harder than I want it to be. But that doesn’t mean that I should abandon the search. It means that I should go to sleep, wake up tomorrow, and try it again.  

And stop texting while drunk. 

Dana Norris is the founder and host of Story Club, a monthly show for stories in Chicago. She has been published in Tampa Review, McSweeney’s Internet Tendency, and The Rumpus. She is currently pursuing her MFA in Creative Nonfiction from Northwestern University. She performs around Chicago you may find a list of upcoming shows at

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