The best dating advice I received after ending a three-year relationship and finally feeling ready to “get back out there” came from a coworker: After a date, you have to ask yourself, did you have a good time because he’s fun, or because you are?
This question has bounced around in my mind in the aftermath of many dates with men I’d initially deemed a success. Admittedly, reevaluating a date can be somewhat difficult for me since I tend to drink one too many Dirty Martinis (blame the nerves!), and anyone can seem like a good time after you’re sufficiently sloshed. I also tend to fixate on and subsequently stress over my own behavior. Was I too loud? Too drunk? Too annoying? Does he think I’m pretty? But after the hangxiety wears off and I can focus on my coworker’s initial advice, I play back the conversations from the night before and wonder: Did that man ask me a single question about myself the entire time?
More often than not, the answer is no. No he did not.
This bleak realization has caused me to become conscious of it in real-time. I can remember the number of times I have asked a man a question, thinking that — at the bare minimum — he’ll ask me the same one in return. But no, he is not inquisitive of my family, or my job or my taste in music. After he’s finished his long-winded answer, there is just uncomfortable silence I then fill with another question for him. I am the one keeping the conversation going. I am the reason I had a fun time on this date. I am a tiresome jester who is being paid in Dirty Martinis.
Since it’s been a significant amount of time since I was entrenched in the dating scene, at first I thought this was an isolated issue. Perhaps this was a bad streak of dates. Maybe I talk too much or am more inclined to ask questions because of my profession. Or, maybe, these men were not interested in me. But as I recount these dates, and my frustrations with them, to my female friends, I discover this is not a unique experience. Their eyes get wide, they nod feverishly in agreement and yell, “Yes! This has happened to me!”
“It’s like a war flashback,” Shannon McNamara, host of the podcast FluentlyForward and former single woman, tells me of her dating history. “I had like five [dates] in a row with different guys over a month, and I remember realizing that I wasn’t getting asked any questions.”
As McNamara recalls, not even simple softball questions would be lobbed back.
“You ask somebody, oh, where did you grow up? And then you expect them to just ask the same thing in return, not even come up with a question of their own,” she says. “I thought maybe it was just a fluke of the guy, but as these dates continued, I realized, not only am I not getting asked questions, I’m not even having my own questions returned to me.”
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“So the next few dates I went on, when I had asked questions and they wouldn’t ask questions back, I would sip on my drink and kind of stare off into silence,” she explains. “Literally it would be silent for like 30 seconds at a time. And I was like, oh my God, this is crazy.”
All of the women I’ve spoken to about this phenomenon agree: it’s completely mind-boggling. As McNamara says, you learn these basic conversational skills back in grade school; people have these types of casual but engaged chats with neighbors or the postman daily. Is it so hard to replicate that with someone you’re trying to sleep with?
“The cashiers at Trader Joe’s ask more questions than guys on dates nowadays,” she says.
To understand why this might be happening — and how men can rectify the problem — I reached out to Blaine Anderson, a female dating coach for men and founder of Dating by Blaine, who says the lack of curiosity on dates comes less from a place of self-absorption (although that can certainly be the case for some men) and more from a place of nervousness.
“It’s easy for them to just talk about something that they know about rather than thinking of thoughtful questions to ask,” Anderson offers.
Unfortunately, the men who aren’t asking questions on dates are likely oblivious to their behavior, she adds. So if you’ve never reflected upon your attentiveness, let this be a wake-up call.
Regardless, if you’re a dating man interested in having better conversations and, in turn, better first dates (and psst you should be), Anderson has some grade-A advice — because even if you are asking questions, you don’t want to bombard your date with them.
“You don’t want to fall into the category of peppering her with questions so it feels like an interview,” she says, “You also don’t want to be on the other side of the spectrum that is not asking any questions.”
“The goal should be somewhere in the middle of a balanced conversation. I tell clients that they should aim to keep her talking 70% of the time and their talking to 30% of the time. Realistically, good conversations tend to be close to a balanced 50/50, but if you are concerned that you’re talking too much and not asking enough questions, aim for the 70/30.”
In terms of what questions to ask, and how to pull the conversation thread, Anderson suggests diving deeper into a surface-level question on one topic before moving onto talking about something else.
“So if you ask her a question like ‘How long have you lived here?’ and she says ‘Three years,’ you could continue with something like ‘What brought you here initially?’”
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Meet the companies offering approachable, design-forward and effective pleasure productsOverall, how present you are with somebody is a great indicator about how much you respect and care to be there with them. Even if you don’t want a second date with that person, you should absolutely practice being present — especially in today’s phone-reliant world.
We’re all guilty of it: When there’s a moment of silence, we pick up our phone and look at it. When there’s a lull in the conversation or we’re feeling slightly awkward, we check the time or absentmindedly open random apps.
“Your phone should not come out of your pocket for any reason. If you have an Apple Watch, take it off,” says Anderson. “If you can eliminate that, you’ll be doing yourself a big favor, and you’ll be ahead of a lot of other men and women going on dates.”
Ultimately, you’re going to have better conversations — and stand out among the rest of these bozos — if you aren’t distracted.
“Our brains are moving a mile a minute, keeping up with social media and inbound notifications. The more you can train your brain and yourself to be present, the more you’re going to be able to pick up on subtle cues that she is inevitably giving you of what she wants to talk about,” she says. “Is she excited? Does she perk up when you ask a certain question or a certain topic is discussed? Dive deeper into that.”
If you implement these practices, at the very least, you won’t get roasted by her and her friends during the post-date debrief. At best, though, it could be the start of a beautiful relationship.
“He was asking tons of questions and it felt like a normal conversation,” McNamara says of her now-boyfriend on their first date. “There was back and forth. It was just a natural progression.”
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