Hi! I’m Steve Dean, and I've been an online dating consultant and coach since 2011. Over the past decade, I’ve seen over 500,000 online dating profiles across over 250 different dating apps. Every day I see the same mistakes from both clients and friends, so I’m finally sharing my best tips and practical considerations here on my blog! If you ever want to dig deeper or chat with me directly, I encourage you to book a quick call with me on my coaching page.
Dating app conversations were never meant to be just “hey what’s up” or “how was your weekend?” When done right, they can be delightful exercises in creative, empathic writing that lead directly to memorable dates.
HOW TO GUIDE YOUR DATING APP CONVERSATIONS TOWARD IRL DATES
First and foremost, let’s be clear about something: every single person on the other side of the screen is living a life as vivid and complex as your own. They have pre-existing obligations to their friends, family, employer(s), and to themselves. Their phones lure their eyeballs with dozens of attentional bids per day (or per hour) from dozens of apps. So let’s start things off with a deep breath, and be relaxed and forgiving, because the last thing you need to do is get angry or impatient in response to an internet stranger.
When you’re planning to message someone, give yourself a moment to creatively imagine a day in their life, based on all the info you can glean from their profile. What is it that would make their day a bit better? What might your message notification lead to that could cause them to smile, to be intrigued, to feel that it’s worth responding thoughtfully, and maybe even, dare I say, look forward to meeting you? Given that app-based dating reduces us to mere letters and photos on screens, we rely on our messaging to add some zest and dimensionality. Do not shy away from sending longer, more thoughtful, more practical messages that make it easier for someone to mentally estimate what kind of commitment you’re looking for. For instance, asking the generic, “Drinks this weekend?” doesn’t help someone understand which day, time, neighborhood, vibe, or duration to plan for, and may consequently lead them to opt instead for someone who put more forethought into their communication.
For the majority of dating apps, merely greeting someone is not enough. Some dating apps have even begun automatically replacing users’ “hi” and “hey” messages with other prompts!
A little heavy-handed, sure, but maybe these algorithms deserve a little credit for saving our inboxes from the next 500 “hey”s, “hi”s, and “hello”s.
But, asking an open ended question without any context can also be a problematic strategy that can lead to being ignored. When you ask someone a question, you’re requiring them to subsequently supply you with content, which is a form of work. To respond, they must now allocate attention toward sating your curiosity, and with no guarantee you’ll respond again. Questions like “how was your weekend” can be equally tedious, and they do not make it any easier to meet up IRL.
My rule of thumb is that if you’re going to ask a question, you should give context for the question, as well as an answer of your own. For instance, rather than “What’s your favorite taco spot in East Village?” I’d opt for going the extra mile. Practice adding some depth and dimensionality to your message, along with as much specificity as you can. Consider, “Loving the 🌮 onesie you’re sporting in your 3rd photo — NYmag actually mentioned a new taco truck opening Saturday in East Village! You down to taco up and wander over to watch the sunset from pier 35’s big swings?”
But messaging can still go so much further! Rarely are we confined to a single thought, or to a single message. I’m certainly not recommending that we become pushy, but there is absolutely no harm in adding relevant details to an initial message to make the logistics easier for our match, and to create space for their own creativity. Consider the previous message about tacos and imagine this as a followup after you’ve matched:
“I can meet at the taco truck at 6pm. If you happen to be freed up earlier in the day, I’ll be on a Central Park foraging tour from 2–5pm. No plans before 2, so if you’ve got any fun ideas for pregaming a foraging tour, I’m all ears. My number is 555.555.5555.”
At the end of the day, apps are here to make it easier to find people we can connect with. Apps provide us with things like curated profiles and photos, compatibility preferences, and location-based matchmaking. They do a lot of the work! But if our goal is to meet up IRL, the onus is on us as users to go that extra mile and reduce the friction even further. Thoughtful, practical, specific messages are our best tool for making this happen. The more proactive, practical, and creative you are in your online interactions, the more fertile the soil where your future friendships and relationships can grow. 🌳
But, always remember that people can be busy. Life happens. Not everyone checks their dating app messages every day, or even every week, so remain patient, and mindful. If a few days go by without a response, it’s fully reasonable to leave one last followup message — always practical, never pushy— like, “Here’s the taco truck article btw: [link]. That one Brooklyn resident’s review is what sold me on it. PS if you can’t make this weekend, next weekend I’m going on an Arepa quest!”
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That's it! Do you feel more confident about how to craft messages on dating apps now? Have you come across other messaging styles that have worked for you? Please share them here in the comments!
Want to chat with me directly? I offer free diagnostics calls where we can talk about your dating history/goals, and decide what your best options are moving forward. You can book a call with me anytime directly from my coaching page 🤗
Author's Note: I originally published this on the Kindra blog, and am sharing a modified form of it here for ease of access.
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Further Reading…