Dating app conversation tips from bestselling romance writers

It’s the dream: Find a smoldering someone on a dating app, match with them, and quickly launch into a conversation filled with subtle compliments, definitive date night plans, and witty repartee.

According to research conducted by Preply, — a language learning app and platform, – more than 70 percent of dating app users surveyed said it’s possible to engage in meaningful conversation, and even fall in love with someone, before ever meeting in person (having only spoken on an app).

The challenge, of course, is getting there, shifting from the notification that “It’s A Match!” into dialogue worthy of a Shonda Rhimes production. It’s a daunting task, so we brought in the pros: rom-com authors.  All with books jam-packed with quippy dialogue out this spring and summer — to get their expert takes on how to write witty banter.

“Impeccable dialogue is what distinguishes romance writers from every other genre,” says Mackenzie Newcomb, founder of Bad B*tch Book Club (a virtual book club of more than 20,000 members dedicated to uplifting female-identifying readers, authors, and protagonists). With that in mind, here are five acclaimed romance writers’ tips and takeaways for dating app dialogue.

Emily Henry: Embrace your own sense of humor and surprise your matches

Emily Henry, author of New York Times bestsellers like Beach Read and People We Meet On Vacation, as well as the just-released Book Lovers, is, arguably, the queen of quippy dialogue. Hers are the types of books that make you laugh out loud on the subway, the kind you’ll be reading until 2 a.m. when your roommate texts to ask, “Why are you awake and cackling right now?” (I speak from personal experience.)

One of the most powerful elements of her writing is that it often surprises readers — either taking jokes a step further than you expect them to go, or breaking sentimental moments up with silly retorts. This same approach can be applied to dating apps. In Henry’s words, “one of the prime elements of humor is that element of surprise.”

“When I’m writing dialogue, I’m thinking of conversation in a way where one person puts something out there, and instead of just saying the natural response that proves you received that, you’re kind of building on it,” she explains. “Take what [your match] has given you, and instead of just confirming that you’ve heard it… throw it out in a more extreme direction.”

Consider, for instance, that your match confesses they’ve just gotten a terrible haircut. Rather than insisting that they look fine, you’re sure (the standard response), Henry suggests throwing out a fun, light-hearted comment instead. Like, “That’s the worst. But somewhere in the world, two otters are holding hands right now. And I hope that fact makes you feel a bit better.”

Will it always land perfectly? Probably not — but that’s not necessarily a bad thing, Henry says.

“If you have a specific sense of humor, you kind of want to know if [the person] you’re talking to can hang with that, or if they’re going to be put off by it,” she says. “It’s kind of a good litmus test.”

Casey McQuiston: Keep up the pace and text like a real person

Another expert in crafting quick-witted banter (for all ages!), Casey McQuiston is the author of New York Times bestsellers Red, White & Royal Blue and One Last Stop, plus the newly released young adult novel I Kissed Shara Wheeler. Their characters are known for being sharp-tongued and big-hearted, and the resulting dialogue pops off the page – making everyone and their mother wish they could be best friends with Alex Claremont-Diaz and Prince Henry (myself included).

Their secret? “When I’m writing dialogue, I kind of write it out like it’s a script or a screenplay,” McQuiston says. “I take all of the other factors out… I’m literally just going back and forth, writing line, line, line, line, line. And I think that’s how you get that really strong flow; where it’s not halting, it feels like it has a really nice, natural rhythm to it.”

Additionally, McQuiston says you want to ensure your characters sound like real people.  “Nobody would come back to an off-hand remark with a long sentence with a bunch of multi-syllable words and exactly the right thing to say,” they explain. “You have to let them sound like a person.”

These principles apply to dating app conversations, too: “You need to keep that rhythm up, you need to keep that pace up,” McQuiston says. “Big blocks of text or perfectly crafted sentences are going to make people’s eyes kind of glaze over… I think the ultimate advice is just never make them think you’re trying.”

And if you don’t naturally have that sense of comedic timing? “Watch things that you think are funny,” they advise. “Just try to internalize that rhythm… That’s a huge help.”

Hannah Orenstein: Paint a picture of your life (and be curious about others)

Hannah Orenstein has been deemed “the master of the modern romance,” and with good reason. The author of four acclaimed romantic comedies — including the forthcoming Meant To Be Mine — and the deputy dating editor at Elite Daily, Orenstein is well-equipped to dish out banter-related advice, especially when it comes to dating apps. From her vantage point, the stronger and more illustrative your profile is, the stronger your conversations will be from the get-go.

“Instead of [saying] you just like pizza, say that you studied abroad in Italy and your host family taught you how to make pizza,” Orenstein advises. “Giving those kinds of really, really concrete details gives people a vision of what your life looks like. And the more you do that, the more clearly they can possibly imagine themselves fitting into your life.”

Similarly, use your match’s profile to mine for those character-defining details and conversation starters.

“When you’re writing, you have to be imaginative and figure out, like, what are all of the different parts of this person’s life?” she says. “You can use some of those same skills when you’re on a dating app. So, ask really interesting questions. Ask the question you think other people might not necessarily ask… Those kinds of conversations can often take you in really interesting directions.”

Jasmine Guillory: Ask questions

To that end, Jasmine Guillory — the prolific New York Times bestselling author of The Proposal and just-released By The Book (among others!) — also recommends asking questions of your matches and using that as an opportunity to unearth who, exactly, that person is, just as she does while drafting dialogue in her novels.

“I really think about the characters,” Guillory says. “What attracts them, what interests them, and what qualities of themselves do they want the other person to know?”

Once you’ve gotten a better feel for your match’s personality, “have fun with it!” she says. “Express your personality, make a joke or two, and most importantly, if you’re not feeling it, trust your gut.”

From Guillory’s perspective, the best banter, — “fictional or real,” — happens when two people clearly don’t want the conversation to end, “even (or sometimes, especially!) when they’re fighting.” (Think Maddie and Theo in The Wedding Party.) In other words, don’t stress about double-messaging or who has the last word. If you’re enjoying it, simply let the conversation flow.

Ashley Winstead: Don’t be afraid to take risks

Ashley Winstead is the author behind the enormously-charming political rom-com Fool Me Once, as well as nail-biting thrillers like In My Dreams I Hold A Knife and the upcoming The Last Housewife. Her characters range from hot messes to vengeful former cult-followers, and all of her books are full of surprises (be they hilarious or blood-spattered). It’s no shocker, then, that Winstead’s guidance for crafting great banter is all about taking risks and embracing the unexpected.

“The number one thing is that good, quippy banter is surprising,” Winstead says. “Always go with the verbal or written choice that is going to cause raised eyebrows or a little gasp… The unexpected choice, I guess.”

Much like Henry, Winstead also suggests incorporating an element of surprise to your messages. “In that risk-taking theme, let your characters — or let yourself — say the things that you think are going to surprise that other person. Because that surprise often leads to delight.”

Let their words of wisdom guide you on your next dating conquest; we’re rooting for your happily-ever-after.