Dating App Messaging — Everything You Need to Know

Tips for escaping the digital slog & optimizing our messages to meet IRL

Feb 19, 2025

Despite the fact that the average length of a first message on most dating apps is less than 10 characters, dating app conversations were never meant to be just “hey what’s up” or “how was your weekend?” When done effectively, they can be delightful exercises in creative, empathic writing that lead directly to memorable dates.

FIRST, ASSESS CONTEXT

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, communities, employer(s), nation(s), and to themselves. Their phones lure their eyeballs with dozens of attentional bids per day (or per hour) from dozens of apps. So take a deep breath and tap into your imagination and creativity, 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. Take the time to imagine how your message will be received. The person reading your message could be on the subway, at work, out with friends, or home making dinner. They may be feeling flirtatious, bored, tired, or traumatized.

Remember, “according to various studies, approximately 65-85% of women have experienced catcalling in their lifetime,”1 so take special care to ensure that your messages never evoke catcaller energy. You can’t control someone else’s context, but you can proactively empathize, imagine some scenarios in which your message might be encountered, and revise accordingly.

CHANNEL YOUR CREATIVITY TO GENERATE GOODWILL

For inspiration and motivation, imagine what 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? A particularly good message could fill someone with anticipation, encouraging them to imagine you doing something enjoyable together. Even if you end up not being compatible, a good enough first message might make them think of which friends of theirs they’d recommend you to.

One method I use for determining whether my profile & messages are up to snuff is to envision my parents, siblings, grandparents, and/or friends all reading over my shoulder. Would they think I’m coming across as authentic, kind, and thoughtful? Would they be proud?

BE MUCH MORE SPECIFIC/DETAILED THAN YOU THINK IS “NORMAL”

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 practical messages that make it easier for someone to assess what a date (or a future) with you could entail.

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.

ASK QUESTIONS; OFFER ANSWERS + LOGISTICS

Merely asking an open-ended question without any context can get you ignored. When you ask someone a question, you’re requiring them to subsequently supply you with content, which is a form of labor. 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. The average female dater in particular gets bombarded with these sorts of messages every Monday morning.

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?” 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 being pushy, but there is no harm in adding relevant details to an initial message to make the logistics easier for your 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, please do share! For ease, my number is 555.555.5555.”

As a personal example, this message exchange I had while traveling led directly to a date. Note that she referenced a line in my profile about secret events, then gave fun, unique, and practical details about her suggested date venue, and she followed up with her availability!

THE STRUCTURE OF A COMPELLING FIRST MESSAGE

Here’s what I believe are the key elements of a message that will help someone feel maximally empowered to respond:

Why You? | Prove you’re alive, approachable, and relevant to them
Whether online or offline, social proof/trust is an essential element of dating. It’s how people assess whether we’re a safe, reliable bet for dating, for friendship, or for introducing to other communities and confidantes. Make yourself come alive by referencing specific things in their profile and connecting them with personal anecdotes that no one else in the world would have.
Why Them? | Communicate your interest with curiosity and kindness
What drew you to them? What might you be able to learn from one another? What have they already taught you via their profile? Ask meaningful questions that you genuinely want to know the answers to.
Why Meet? | Build anticipation and logistical foundations for a possible meetup
Name some physical spaces and activities you’ve been meaning to explore. Are there any playful bucket list items you’re hoping to accomplish this year? Are there event series, theater productions, dance gatherings, talks, or intramural sports on your radar? Are there particular times of day/week when you’re most free? Make a clear suggestion, and if space allows, provide alternatives in the event they’re not available for (or interested in) what you suggested.

MESSAGING CADENCE

Messaging cadence is a key component of rapport. I’ve had people unmatch when I didn’t reply within a day. It’s hard to know when people will next be online, so the best time to send a reply is right after they’ve sent you a message. If you’re going to take longer to reply, it’s helpful to share a bit about what your life has looked like in the interim, so they can further assess how you spend your time (and how you might communicate in relationships).

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!”

Here are a few additional tips on cadence:

📜 Send about as much content as you’ve previously received, or a little more.
Don’t shy away from sending a few short paragraphs, especially if it lets you be more vivid, vulnerable, and forthright with logistics so you can expedite the process of actually meeting up. It’s too easy for conversations on dating apps to degenerate into noise & fluff. You’ll stand out if you’re heartfelt, curious, playful, and action-oriented.

🤳 Be a better texter. Use voice-to-text liberally.
What may seem like “way too long a text” is typically the equivalent of ~3-4 sentences, yet a 5 minute conversation with someone on the phone can constitute 100+ sentences. Giving people more information is a proactive gesture of goodwill and responsibility. It empowers people to make better decisions, and to share more of their reality with you.

🕘 Best messaging times
These vary based on intentions (dates vs. hookups), but typically, users are most active Sunday evenings. Personally, I’ve found a lot of success in sending messages on Tuesday mornings in which I propose a weekend date. It escapes the hubbub of a Monday and gives a few days’ buffer for planning additional date logistics.
🍑For a hookup or something shorter-term, it can be worth messaging people when they’re most likely eager to get outside, e.g., Thursday and Friday nights, but that’s also when you’ll face the most intense attentional competition. It’s during these times that you may most benefit from paying for specific dating app features that let you stand out (sometimes called “boosts”) or skip the line / indicate advanced interest (aka “super likes”).

WHEN TO TRANSITION OFF THE APP?

Before suggesting a date or suggesting communicating off-app, seek to confirm that the person you’re talking to is real, has a vibe that you’re into, and has shown some degree of rapport with you. This is for your own safety, and to reduce the likelihood of going on bad dates. Be mindful that anytime you’re sharing personal information on the internet, there’s the potential for misuse or abuse. Every single dating platform has spammers, scammers, bots, and escorts.

Some people prefer to call, video chat, or do a short meetup before transitioning off-app, to preserve their privacy and not give out their phone number. For those people, I recommend proposing a first hangout in a neutral public space (cafe or food court). Don’t make reservations, and don’t pick a place that’s hard to leave (e.g. a sit-down restaurant). The higher the stakes, the more likely they may flake.

Note that rapport can form within mere minutes, so prioritizes being forthright and upbeat. Don’t be afraid of actually asking someone out if they seem aligned. You can just as easily ask them for their Instagram or preferred social handle, as that will help you stay ambiently in touch if either of you are busy/traveling and can’t meet up straightaway.

WHEN NECESSARY, DECLINE WITH POLITE CONFIDENCE

While you’re messaging potentially dozens of people, you may run into moments where you realize you’re simply not compatible enough to continue making the effort. It’s good to have a thoughtful message you can send to any matches who you’re choosing not to prioritize.

Of course, you might use different messages depending on whether you're breaking things off within the app before even meeting, versus over text after having been on one or more dates.

The simplest boilerplate rejections can be as simple as:

“You’re great, but I’m not feeling the romantic vibe”

“Hey I see your messages and thanks for following up but I don’t think we’re a good fit”

If you want to go a bit more informative and vulnerable, consider something like:

Sorry, this is not going to work out. I’m already foot-dragging internally and my gut is saying to end things. [Insert reasons if you care to] I think it’s more advantageous for you to spend your time investing in someone who actually wants the same things as you and feels both attuned and aligned. I hope you can spend your time finding that person.

At the end of the day, dating 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 and creative we are in our online interactions, the more fertile the soil where our future friendships and relationships can grow. 🌳

Have you come across other messaging styles that have worked for you? What questions still linger? Please share them here or message me anytime!

PS — A first message is only as good as the profile that backs it up. I gave tips on crafting a compelling profile during my Reddit AMA.

Need help with dating, personal development, or navigating relationships? Let’s talk! I’ve been a coach and dating app consultant for nearly 15 years! Schedule a call with me and we’ll talk through your life, goals, struggles, and strategy. First call is free, and I’ll do what I can to point you in the right direction!