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My Guide to Starting Conversations on Dating Apps

I get asked often about the “best” ways to open up a conversation with an attractive stranger who’s caught your eye IRL - and my answer usually is not to overthink it. In person, I tend to say to clients, what you say to start a conversation doesn’t matter much - your demeanor, intentions, and body language overwhelmingly speak louder than the actual words that you choose.

That said, dating apps have changed the first impression game - and often, your opening line is one of only a few things that your match has to go on to assess your personality.

With that in mind, I’ve created a short guide to dating profile conversation openers that will help you to put your best foot forward on apps.

So. Let’s talk online dating conversation openers.

Overall, I tend to recommend going for a mix of funny and flirty when starting a conversation with matches - although, if you're like me and "funny" doesn't come naturally - genuine and enthusiastic works, too.

As a general rule of thumb, flirty works especially well for casual swiping, and genuine enthusiasm works especially well for more serious connection-searching, but both can yield fantastic results, whatever your goal.

Messages that stand out are usually ones that are a little bit unexpected. The saying, "You need to know the rules to break them" applies here - your goal is to show that you're aware of what's expected - and then do it with a twist that leaves the recipient feeling pleasantly surprised.

If you're a woman messaging a guy, my favorite way to do this is to go off-script with gender roles. Overall, women message first less frequently than men do, and men tend to initiate compliments more frequently than women. As a female dater, if you flip the script and do either, you immediately stand out as confident and playful.

Okay! Now it’s time to dive into my two formulas for first messages.

Formula One: Funny + Flirty

Iteration One: "Are you really . . . ? Statements.

Start by asking “Are you really . . . ?” And then follow it up with a line about that statement - and try to make it cute and flirty. (Adding a cute emoji never hurts, too.)

Example: “Are you really a tax attorney? Damn - I guess I didn't realize that there could be tax attorneys that were this cute. 😉”

Example: “Are you really a dating coach? Does that mean that you're basically the female Hitch? Should I be worried? 😉”

Iteration Two: “What’s the worst . . . ?” scenarios.

“What’s the worst” scenarios are a great way to share a funny story about dating - but the trick is to keep them (and the conversation) lighthearted. Don’t tell a story about the time you ran into your ex on the app, or the time you went on a date and nobody showed up, which also happened to be the day that your ex from high school got married. The idea is to share a few memorable details that make an amusing anecdote.

Example: What's the worst Tinder opener you've gotten so far?

Example: What's the worst date you've ever been on? Mine involved _____, ______, and a _____.

Iteration Three: The Cheeky Compliment.

A little bit of humor or light teasing can go over really well with this one.

Example: I swiped right on you ONLY because of _______.

(Flirty or funny both work well here - i.e., "that smile," "those eyes," "your dog - I want your dog!" "that hat - I'm a big Red Socks fan.")

Formula Two: Friendly + Enthusiastic

Iteration One: Friendly + Ask a Question/Make a Statement About Something on Their Profile.

This is an iteration of the “Are you really . . . ?” statement from earlier - but with the idea of establishing immediate rapport and something in common to talk about. People like commonality. That’s often why they’re matching with you - they see something on your profile that they like or resonate with.

The beauty of the profile statement is that it works with almost any fill-in-the-blank, and relies on connection, rather than you being clever or funny.

Iteration Two: Direct. State a Commonality + State a Value + Ask Them for More Info.

This one takes the direct approach - which is a great idea if you’re looking to establish genuine connection and to filter out people who aren’t aligned. Stating a commonality establishes rapport and a conversation topic, and then following it up with your own values invites someone to state their values, too - which puts the two of you one step closer to assessing whether your values are aligned. And values alignment is one of the strongest predictors of connection and longer-term relationship potential.

Example: "I swiped right because I saw on your profile that you're a big traveler. I am, too - being able to understand that everyone lives differently is a big value of mine. What do you love about traveling?

Listen, dating in 2021 can be a struggle for everyone. When you’re feeling over it and breaking the ice with someone new feels hard, it can feel like app dating is impossible — or like maybe you're the undateable one.

You are not impossible, or gross, or weird, or unable to start a conversation with an attractive stranger. And now you have prompts to do exactly that! So - go forth. Flirt. Tease. Connect. Build rapport. Have fun! Dating can, in fact, be fun. And now that you have a cheat sheet to starting conversations - GO AND START CONVERSING ALREADY.

Love you! But really - go now. Bye.


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