How To Start A Good Conversation On A Dating App

Dating experts share tips for messaging a match and good openers you can try on Tinder, Hinge, Bumble and more.

I met my now-fiancé on Tinder in 2013, back when dating apps were a new phenomenon. In his bio, he mentioned something about a frozen yogurt chain that I happened to frequent. After we matched, I dashed off a quick message asking what his go-to order was.

“Strawberry yogurt with Cap’n Crunch,” he told me. Deeming this a trash order (I’m a cookies and cream with Reese’s person myself) I wrote back: “That’s offensive.”

It was, perhaps, an overly sassy reply to diverging fro-yo preferences, but he found it charming and the conversation unfolded from there.

Truthfully, I didn’t put much thought into my opener, but it turned out to be a good one. We went on our first date soon after and have now been together for almost a decade.

Even though my approach was successful, I’ve been out of the game a long time now, and I’m no expert. So, I turned to actual experts for their best tips for striking up a conversation with a match.

Open with a question

Keeping a list of fun and interesting questions in mind can make initiating a conversation less intimidating. You want them to be open-ended questions, rather than “yes or no” ones, said dating expert and matchmaker Jasmine Diaz of the Diaz Dating Group.

“Consider topics that correlate with your interests: Where is your favorite place to travel? Who is at the top of your Spotify playlist? What is the most adventurous thing you’ve ever done?” Diaz said, advising against bringing up touchy subjects like politics or religion right off the bat.

Pull inspiration from their profile

A quick scroll through their profile offers insight into interests you may share and creates a gateway to quality conversation.

“Don’t be afraid to reference that cool hiking photo or silly prompt that made you swipe right to begin with,” Diaz said.

If they posted a picture from Mexico City, you could say, “I’ve always wanted to go! What was the best thing you ate there?” If they mentioned that “Curb Your Enthusiasm” is their top show, you could ask about their favorite character or episode. And if something in their profile cracked you up, say so, Diaz suggested.

Play ‘this or that’

Another good opener that often gets a response is a simple “this or that” question, said OkCupid dating coach Damona Hoffman, host of the “Dates and Mates” podcast.

“Chocolate chip or Oreo? Beer or wine? Dogs or cats? East Coast or West Coast rap? Pick something that you have a strong opinion about and whether or not you agree, you’ll almost always start an interesting conversation,” Hoffman told HuffPost.

Avoid boring, dead-end questions

Stale openers like, “How was your week?” or “What are you up to this weekend?” often lead to conversations that fizzle quicky, said dating coach Lily Womble, founder of Date Brazen — if they get a response at all.

“Opt for something a little deeper to cultivate a more intentional connection from the start,” Brazen said. “You want your opening question to qualify the right people and disqualify the wrong ones.”

Opening with dry, predictable questions like, "How's your week going" are unlikely to lead to interesting conversation.
mikroman6 via Getty Images
Opening with dry, predictable questions like, "How's your week going" are unlikely to lead to interesting conversation.

Womble prefers more intentional conversation starters that go past the surface-level stuff. If that’s more your style, too, you could ask something like: “What’s brought you joy this week?” or “What’s your favorite controversial opinion?” or “What’s made you laugh hardest this week?” she suggested. “Don’t be afraid of sounding too intense.”

“Remember: the right person for you is also looking to find the right person to get off the dating app,” Womble added.

Be playful

Anyone who’s been on dating apps a while has had the same ho-hum exchanges over and over. Break up the monotony and set yourself apart by being a little playful, said online dating coach Joshua Pompey of Next Evolution Matchmaking.

“If I saw a picture of a women with a dog, instead of saying, ‘That’s a really cute dog, what breed is he?’ I might say, ‘Is your dog currently accepting new members to the pack? If you want to put a good word in for me, I happen to be a pro at sneaking treats under the dinner table.’”

The latter taps into their love of dogs, while also showing you’re fun and don’t take yourself too seriously.

It “relieves the person you’re messaging from the same boring questions he or she is used to receiving,” Pompey added.

Ignore traditional gender norms

If you’re a heterosexual woman on a dating app, you don’t need to wait around for the guy to make the first move. According to OKCupid data, during the pandemic, women have been increasingly more likely to be the first to send likes and messages — a trend that continues today, Hoffman said.

And it pays off: “Conversations actually last longer when women initiate,” she added.

Don’t lead with sex

When you start talking about sex right out of the gate, you’re sending the message that you’re more interested in finding a hookup than making a genuine connection. You can be flirty without being vulgar, Diaz said.

“Frame your questions about their interests, but don’t skimp on the charm,” she said. “For example, if a profile mentions that they’re a foodie, ‘I’d love to cook for you’ or ‘If I could make you any dish, what would it be?’ is a beautiful start to a flirty conversation.”

Be authentic — it’s your superpower

Don’t downplay the things that make you you: your witty sense of humor, your breakfast burrito obsession or your passion for fostering dogs. Lean into these things, rather than trying to project what you think your match wants to see.

“The pressure to become a newer, improved version of yourself online is real, especially when we equate right swipes and matches with personal value,” Diaz said. “But authenticity is your superpower.”

Diaz believes much of the discontent around online dating these days stems from a lack of authenticity in the space — the rise of romance scams and catfishing have all made singles more cautious.

“Showing your true self is more desirable than ever,” Diaz said.

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