How To Have A Conversation On A First Date

I’m going to want to go out with you again if I feel like you talked with me, not at me.

The first time there’s an awkward pause on a date, I happily fill it, asking a question on an earlier subject, or segueing toward something new.

The second time there’s an awkward pause, I wait a beat longer to see what he’ll do before asking another question and urging the conversation forward.

The third time, I wait for a while. A long while. I sip my wine, chew slowly, gaze around the bar at other couples chatting away. The silence is uncomfortable, but so far we’ve discussed his work, his hometown, and his thoughts on the place of the anti-hero in the popular canon. I’m waiting for him to give me some indication that this isn’t just an exercise in self-revelation but a mutual attempt to learn about another person.

So far, the only question he’s asked me is whether I’d like to split a bottle.

But the silence continues. He looks at me expectantly, so I sigh and ask him something else (“What was it like meeting Billy Corgan?” “Performance art, eh? What’s that all about?” “So you brew your own beer, huh?”), to which he responds enthusiastically. And though the evening continues for another hour of (his) stories, that third silence was when the date officially ended.


After my most recent date went the way of the question-less, I posted on Facebook:

Pro tip: dudes, when you’re on a date, ask a question or two. It makes us think you think we’re people. We like that.

A friend commented, “The best is at the end of a date like that when they gush about how ‘connected’ they feel to you. Cool story, bro.”

I think she’s on to something. Between my open-minded approach (some might call it a low bar), the prevalence of fish in the sea of my mega metropolis, and the ease of access through a myriad of apps, I’ve covered the gamut from Andrew (four of them) to Zev. They do not all, by any stretch of the imagination, fall into the bucket of the questionless monologuers, but I’ve had my fair share (two of the Andrews, for example). What I find so striking about the monologuers, is that they all, without fail, think the date went spectacularly.

What makes a good date? In my book, I’m looking for stimulating conversation and the mutual understanding that we’re trying to get to know each other to decide if we should spend any more time in each other’s company. When a guy never asks me any questions about myself, but happily waxes poetic about his CrossFit regimen, it tells me that he doesn’t want a conversation partner, he wants an answering machine that he can talk at for half an hour. When he’s thrilled with the date at the end of the evening, it tells me that the thing he likes about me is not me, but my ability to nod while he’s talking. He may feel truly heard and appreciated (“Cool story, bro”), but I don’t.

My original Facebook post suggests I think this is a gendered problem, but the truth is, I have no idea. My evidence pool is limited to men, but for all I know, there’s an equally large segment of monologuing women out there. I would venture to guess, though, that the economics of dating (especially online dating), contribute to the male monologue phenomenon.

Online dating unfairly favors women. For the most part, we can wait to be approached and then take our pick (I’m not advocating this strategy, just pointing out that it is possible for women but not for men). This system creates an incentive for men to strive to impress their dates, while women sit back waiting to be impressed. The monologuing first date is just the flesh-and-blood incarnation of that online phenomenon. In an effort to impress, guys try to tell their best stories, relay their best jokes, share their smartest opinions, because they know that back home, she’s got an OkCupid queue waiting.

And while I am impressed that you walked the Camino de Santiago with a sprained ankle, I am not impressed with how little interest you have in getting to know me. I’m not going to want to go out with you again because you’re a sturdy hiker; I’m going to want to go out with you again because our conversation was fun. I’m going to want to go out with you again if I feel like you talked with me, not at me.


Look, I know I’m a nosy New Englander. I’ve been known to pry, to preemptively assume familiarity, to get too personal. I recognize that not everyone appreciates my conversational style and that there are many, many ways to get to know someone. On a first date, however, especially a first date born on the Internet, I do think some question-asking is a necessary component to gauge compatibility.

Are there exceptions? Sure, if you’re on an awesome joint rant about, I don’t know, registering for Obamacare, or your love for dystopian tween literature, or Peruvian cuisine, don’t halt your momentum to politely ask, “So, do you have any siblings?” But in my experience, the joint-rant dates, while awesome, are few and far between.

So, dudes (and ladies, if you’re guilty of this) if the end of the date rolls around and you’re like, “Damn, that was fantastic. She really gets me. I feel like she understands where I’m coming from and really wants to know me,” ask yourself this: Would she say the same?

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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