Have Fun On Your Date Tonight, Wherever That Is

An investigation into men who don't make plans.

by Sophie Vershbow

At 10:13 a.m. last Wednesday, I found myself in a position I’ve been in more times than I’d care to admit: exasperated that the details of my date that night had not yet been confirmed. “Another date night with no idea where I’m going or when!” I texted my best friend. “Same!” she wrote back immediately, herself in the exact same position 1,500 miles away in Austin.

During college, neither of us would have predicted that the hardest part of dating in our mid-30s would be getting men who have already asked us out on a date to tell us where and when to meet them.

I wish we were the only people experiencing this flakiness — something I’ve seen get increasingly worse during my decade on the apps — but unfortunately, we’ve got company.

When I posted about it on Twitter (never X), my feed was flooded with replies from other women sharing similar experiences of planning hot potato.

“This sh*t makes me insane and I can’t understand the reason for it. Like, it doesn’t feel like they’re just forgetting to pick, since I will approach the question multiple times? Are we in a stand-off? Is this a game of chicken?” wondered @emilybihl.

Erin Resnick, a 34-year-old digital marketer, is similarly baffled, having been recently ghosted after confirming what neighborhood they’d meet up in the day before her date. While this was the first time someone had blatantly bounced the day of, she said it’s emblematic of a larger pattern in her dating life.

“I've had several guys drop the ball with follow-ups… ask me out and then never follow through after I offer days and times. When I first started experiencing it I would question myself and be like ‘did I say something wrong?’ but I've become desensitized to it and just find it highly annoying.” Erin never heard from the ghoster again.

Why Are People Like This?

To better understand the other side of these heterosexual dating dynamics, which historically rely on men pursuing women, I spoke to Nick Notas, a dating coach for men, and Jared Freid, a comedian and co-host of the dating podcast U Up? They both chiefly blame this phenomenon on a culture that enables ghosting on your upcoming date as “the norm.”

“Men love vague plans,” says Freid. “Dating apps were made [by men] so that men could be lazy. And so that men could find multiple options without chance of failure … I think a lot of men get off on the idea of knowing they can get it, but when the time comes they don’t have the energy to go through with it.”

He also pointed out that, unlike being set up by friends or going out with someone you already know IRL, there is no accountability to the stranger on the other side of the screen who is just one of many strangers you’ve talked to this week.

When I posted about this issue, most of the responses fell into two stark camps: dump him and just plan the date yourself. But the world is not an internet comments section and, as both Freid and Notas pointed out, most people’s decisions are more nuanced than they’re going to tell a virtual stranger over a text-based messaging app. Yes, there are bad guys out there who genuinely do not care about inconveniencing and disappointing women, and yes, there are women who expect a guy to do everything for them, but I think most of us are just exhausted swipers stuck in an algorithmic dating app system that countless recent articles have reported is worse than ever.

How Plans Fell Out Of Fashion

Making modern dating even more complicated is the whiplash of heteronormative gender expectations. Historically, men have been expected to pursue women, but we’re not in a Jane Austen novel. As a self-sufficient woman who could make an OpenTable reservation with her eyes closed, am I supposed to take control and plan the date? Or do I wait for the guy to make plans because someone who can’t make the effort to pick a bar for the date he asked me on isn’t worth my time?

For decades, bestselling advice books for women like The Rules, Why Men Love Bitches, and He’s Just Not That Into You essentially told women to ignore men until they like you, yet Notas tells me the most common issue he hears from men is that they’re frustrated women aren’t showing excitement about them. Daniel, a 25-year-old software engineer, backs that up. “If a woman fails to demonstrate an eagerness to meet up, then I am unlikely to consider a serious relationship with her,” he says.

Even Bumble, a company built during the early days of Lean In and girl-boss feminism in 2014 on the premise that women should make the first move, just announced they’re giving men the chance to initiate conversations, too. It’s a lot to have swirling around your head on top of trying to figure out whether you’re romantically interested in someone.

Leaving aside that many women already try to take the initiative on date planning with limited success, and leaving aside that my Hinge profile says my love language is “Making plans, nothing is hotter than a reservation,” and leaving aside that the average woman already puts more effort into getting ready for a date than the average man, I do agree that this is not just a problem of individual bad behavior from one gender but of a systematic issue that hurts everyone involved.

“When I talk to most people, whether it’s men, women, anybody on the spectrum, the answer is all the same: I feel like other people are hurting me and don’t care,” says Notas. “A lot of it is self-preservation, the endless feedback loop of: everything sucks, I’ve been hurt, this has happened to me, I should just avoid this or back out or it’s not a big deal if I don’t communicate. And it’s probably more so coming from a place of their own struggles [rather] than anything else.”

As if I needed more proof after the conversations with Jared and Nick, in the time I took to write this, my best friend referenced above had a date from Raya with a different guy who said to her face that he flaked on their previous attempt to hang out because he’s “just not motivated to meet people I don’t know.”

Should You Just Plan It Yourself?

The question is how to go about making plans with people you meet on dating apps in a way that doesn’t leave you feeling like you nagged a guy into attending the date he likely invited you on in the first place.

For starters, consider just sending the damn text. “I’m super flattered when a woman suggests a date, asks me out, or makes a plan. It’s a huge relief when I don’t have to plan anything and can just be along for the ride,” says Paul, 30, a tech recruiter.

“If you want to be able to feel pursued while at the same time not feel like sh*t, I would say...”

Alternatively, Freid advises giving people the tools they need to succeed. He said, “If you want to be able to feel pursued while at the same time not feel like sh*t, I would say, ‘Hey, this conversation was so awesome, I would love to get a drink sometime Wednesday or Thursday, make a plan and I’m in.’ You’ve given them all the tools, all they have to do is put the house together.”

But there’s a catch, he says. “Some people never wanted to put the house together to begin with, and you just have to understand that’s OK.”