What the worst first dates all have in common

Plenty of single people have witnessed how curiosity dies in real time: It happens seated across from a first date who doesn’t seem interested in asking you a question. Or, maybe worse, it happens when you’re the person who has no questions for someone who seemed like a promising potential crush. The wildest thing about these bleak anti-meet cutes is that no one does this on purpose. No one wants to go on bad dates; few people think of themselves as apathetic conversationalists. Yet, all across this big world, lousy encounters continue. What gives? According to experts, the most important thing for a dater to be is curious about the person they’re meeting. That can be surprisingly hard, in part because many people show up to coffee or drinks knowing too much. There’s Google, for one thing — a surefire way to take the mystery out of any stranger — and then there are the apps that might have helped you find the date in the first place. With their computer algorithms touting compatibility, swiping has flattened our romantic interest. This isn’t to say that people didn’t go on bad dates before the rise of Tinder, Bumble, and OkCupid, but those platforms aren’t as helpful as they seem for actually connecting. Maybe that’s why a reported 1.4 million people left the apps last year. Maintaining some air of in-person wonder is absolutely vital to getting to know another person for real. Here’s how you can keep the joy of meeting people alive, including what to ask. Why curiosity matters so much to dating “I say ‘curious’ more than any other word when I’m with my clients,” Alexandra Solomon, a psychologist and author who teaches at Northwestern University and specializes in relationships, tells me. Solomon explained that whether you’re on a first date or in the 27th year of a marriage, being keen on a partner’s life — their thoughts, emotions, their day-to-day — is integral to healthy relationships. Solomon said that over her nine hours of therapeutic sessions with clients on the day we spoke, she must have used that word a hundred times. “Curiosity is where the spark lives,” Solomon adds. The poetically tragic thing about modern dating is that the apps so many people use, along with accomplices like Google and social media platforms, are curiosity’s biggest killers. Everything that’s helping us to connect with people to go on dates is also capable of sabotaging those dates. Dating app profiles don’t just contain the basic statistics of what we look like, how tall we are, and our hair color. From favorite foods to morning routines, beloved movies to the dorkiest thing about ourselves, dealbreakers to our shower thoughts — we’re told to divulge all these snippets of ourselves on the off-chance that this curated version of our taste and experiences might rustle up a romantic response. What do you ask a person when you know that they love macaroni and cheese and need three cups of coffee to wake up? How do you act interested when they say The Godfather is their favorite movie, but you’ve already talked about how many times they’ve seen it? Do you have to laugh at their line about being an only child because their parents knew they couldn’t do any better, even though they made the same joke on their profile? When we think we know someone already, we might not make the effort to really get to know them. If we don’t make an effort to get to know someone, we’ll be less likely to be interested. [Image: Dating apps might, surprisingly, not be so good for dating. https://platform.vox.com/wp-content/uploads/sites/2/2025/05/gettyimages-2179836771.jpg?quality=90&strip=all] “You also don’t want to build an idea of someone in your mind and be disappointed if they don’t live up to the hype you’ve created,” says Anna Morgenstern, a matchmaker and dating expert. Morgenstern explained that expectation and judgment are big pitfalls when it comes to the apps. If people aren’t using the info we have on apps to imagine a perfect partner and create an impossible standard for romance, then they might be scouring to find a dealbreaker. Maybe it’s an old photo on their Instagram or that they went to the same school as an ex, but some people will find a way to talk themselves out of a date with a potential romantic partner. “If you’re looking for an ick on a potential date, you’ll find one,” she says. Plus, “the date will be pretty boring if you’ve already found out everything about them.” There’s also a cumulative effect from scrolling through our options that can wear us down. Solomon says that biologically, humans are wired to have small personal circles. Swiping on profile after profile, seeing all these faces and all this data about them confounds our human instincts. Going on multiple dates with multiple people via apps that are more or less pretty similar is going to cause some kind of fatigue. One can only have a “favorite book” or “secret bad habit” conversation so many times, even if the answers may be unique. The draw to the most popular dating apps is that they take the stuff we seek in potential suitors — looks, values, education, pictures (possibly holding a giant fish), etc. — and present all of these things to us in a streamlined way. Most apps also allow you to filter these people by how tall they are or their age or ethnicity. By the time one decides to go on a date, the person they’ve agreed to meet has already made it through rigorous romantic sifting, and the promise of compatibility. Theoretically, all this box-checking should lead to more perfect matches, but that’s not the way human relationships work. How to be a more curious dater If knowing too much about a person can kill a date, what about going on blind dates? It’s a practice that feels very much of a time before apps, Instagram, and Google, but it’s the way some people used to date back in the day: being set up without knowing who exactly is going to show up. “A blind date can feel exciting,” Morgenstern, the matchmaker, says, “to give up some of that control and go back to simpler times by trusting a friend or family member with their matchmaking skills.” An actual matchmaker can mimic this kind of useful surprise, too. Morgenstern explains that while her clients obviously know themselves better than anyone else, they might still be limiting their options for a partner. Morgenstern finds them matches they might not even consider. “When you’re too close to your own dating patterns, it’s easy to miss red flags or repeat unhealthy choices,” says Simona Fusco, the founder of Perfect 12, an exclusive matchmaking service that serves high-profile clients. Fusco notes that for many, dating apps can lead to emotional fatigue, hollow interactions, and a lack of privacy, which is why some individuals ultimately view them as a waste of time and seek a more curated and intentional approach to dating. Of course, not everyone is comfortable signing up for a matchmaking service, or can afford to. But anyone could tap into a similar energy by asking friends, coworkers, and family members to set them up. By the same token, we could play matchmaker to our single friends, coworkers, and family members, who’ve ditched apps. Sarah Hensley, a relationship coach and psychologist, echoed these sentiments. She says her clients have started seeking out more organic ways of meeting people — social clubs, fitness, volunteering — and looking for potential partners who are friends with their friends. This discovery process is more exciting than what you’d find on the apps, she says, and “can spark attraction that wouldn’t otherwise manifest.” But even with a more intriguing way to date, there’s still that nagging problem of what to ask someone you just met. Experts I spoke to shared a few of their surefire questions to ask to spark curiosity: * What’s your favorite childhood memory? Do you want to replicate it with your own family someday? * What’s your biggest fear? * What’s something that makes you laugh? All of these questions encourage the person answering to tell a story and have a point of view, and they also make the person asking an active listener. A question doesn’t have to be particularly deep or probing — one expert recommended asking what media personalities, celebrities, and influencers your date follows. The goal of each of these questions is to feed our curiosities. [Image: Remember when Netflix created an ultra-successful franchise on the premise of blind dating? https://platform.vox.com/wp-content/uploads/sites/2/2025/05/gettyimages-1480794830.jpg?quality=90&strip=all] For Solomon, the psychologist based at Northwestern, the best question is “What made you light up this week?” As she explained, it isn’t fixed. The time provides a frame, so your date doesn’t have to go searching the recesses of their memory, but the timeliness keeps the answer from skewing into something generic. It also breaks up the monotony of “best” or “favorite” replies. Of course, some dates are destined to die on the vine regardless of how curious you are. Sometimes you — or your date — could be as eager and endearing as can be, but the spark isn’t there. If worse comes to worst, you could always just go back to the apps, maybe having learned something new.

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What the worst first dates all have in common