Gen Z, millennial, Gen X? Experts reveal who has the 'deepest' conversations on a first date.
Sorry, Boomers!

An older man uses his landline. A younger woman looks perplexed.
When it comes to dating, one through-line exists among generations: people are looking to connect. Now, the length of connection may vary—as might the intensity. Some call it love, some call it sex, some call it just "hanging out." But it's connection either way.
In a study conducted by Zoosk, researchers claim to have "analyzed over 5.7 million profiles and surveyed more than 4,000 daters." Alongside dating expert Haley Quinn, they even talked to people on the streets of London to get their opinion on what seems to be quite a definitive difference in generational dating styles.
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Before we get into the differences, let's first note the similarities. In the post, "How does your generation date?" therapist Nancy Ryan, LMFT, points out that Boomers, Gen X, and a good portion of millennials actually existed before the Internet and dating apps. "A simpler time of landlines, answering machines, and nosy parents who loosely cupped the receiver while yell-whispering, 'It’s a boy!'"
Another common theme? All the dating generations (at least in the survey) overall prefer their first meeting to be a "coffee date." (Some, of course, disagree—but across the board, this polled high, perhaps implying it's best to keep it short, sweet, and non-committal before actually moving forward with someone.) Also according to the study, "Over 80% of daters across all generations think holding the door open for your date is a romantic gesture!" Chivalry is alive and well.
That said, there are unique differences between generations, as dating norms have evolved over time. Wherein there used to be "rules" set by many Boomers and the generations before them, things have changed. "People are freer to follow their heart," Ryan writes. This isn't to say each generation doesn't push their own set of proposed guidelines, with TikTokers and Insta influencers especially dictating advice like "Don't call, never double text," etc. But each age group is a bit less dogmatic than in past years.
One distinguishable—but not surprising—difference is that Boomers prefer a phone chat to texting. This number decreases as the age is lowered. "The majority of Baby Boomers (60%) like to call to arrange a date. This is 13% more than Generation X, 25% more than millennials, and 26% more than Generation Z." Also in descending order is how chatty a first online message is. Boomers say the most, with Gen Z usually messaging the least. (Think: Sup. How u?)
But when it comes to getting deep, there is one generation who takes the cake—and that's Generation X. This was measured in the amount of texts that go back and forth between potential daters, noting they're not just one-word questions and answers. A little more meat on the bones, so to speak.
Some attribute this to your everyday existential crisis hitting some Gen X-ers (and older millennials) right now. Also, possibly being the latchkey baby-busters that they are, maybe they just have a bit more time to get into the "heavy" stuff.
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Naturally, this isn't a one-size-fits-all. Any person of any age, any gender, any sexual orientation doesn't just fit into a box, no matter how many polls are conducted. Gen Zers (and yes, Boomers and all other generations) can and do "go deep," as well. But again, as the generation who didn't necessarily have the tools to discuss trauma, were often left to their own devices, and experienced exponential change in the landscape of the world in a really short amount of time—maybe they just simply want to TALK about it.