10 First Message Mistakes That Kill Conversations

December 14, 2025

You’ve just crossed paths with someone interesting—maybe at a café, a coworking space, or while waiting for the bus. You exchanged a smile, a nod, or even a brief chat. Now, you’ve both opted to connect on a proximity-based social app like Matuvu, and it’s time to send that first message. But what do you say?

The first message sets the tone for the entire conversation. A great one can spark curiosity and warmth, while a misstep might leave the other person unsure how to respond—or worse, uninterested. The good news? Avoiding these common mistakes is easier than you think.

Here are 10 first message mistakes that kill conversations—and how to fix them.

1. Starting with a Generic Opener

Mistake: “Hey, how’s it going?”

Generic openers like this are forgettable because they don’t invite a real response. They feel like a chore to answer, and the conversation often fizzles out before it even begins.

Fix: Reference something specific from your real-life encounter. Did you notice their book, their dog, or the event you were both attending? Mentioning a small detail shows you were paying attention and makes the message feel personal.

Example:

“I saw you reading The Midnight Library earlier—what did you think of the ending? I’ve been meaning to pick it up!”

2. Overcomplicating the Message

Mistake: Writing a novel in your first message.

Long messages can feel overwhelming, especially if the other person isn’t sure how to respond. They might put it off, and by the time they circle back, the moment has passed.

Fix: Keep it short and simple. Aim for 1-2 sentences that invite a response without demanding too much effort. Think of it as a gentle nudge, not a deep dive.

Example:

“I loved your vintage camera! Are you into film photography?”

3. Being Too Formal or Robotic

Mistake: “Greetings. I hope this message finds you well.”

Formality can feel stiff and impersonal, especially in a social setting. It creates a barrier where warmth and authenticity should be.

Fix: Write like you’re talking to a friend. Use contractions, emojis sparingly, and a tone that matches how you’d speak in person. Authenticity is key.

Example:

“That was a great talk at the meetup earlier! What got you into urban gardening?”

4. Using Pickup Lines or Cheesy Compliments

Mistake: “Are you a magician? Because whenever I look at you, everyone else disappears.”

Pickup lines and over-the-top compliments can come across as insincere or even creepy, especially if the other person isn’t expecting them. They can make the interaction feel transactional rather than genuine.

Fix: Compliment something specific and non-physical. Focus on their interests, style, or something they did—like a great question they asked during a discussion.

Example:

“You had such a cool perspective on that panel earlier. Where’d you learn so much about sustainable fashion?”

5. Asking Closed-Ended Questions

Mistake: “Do you like coffee?”

Closed-ended questions (those that can be answered with a simple “yes” or “no”) don’t give the other person much to work with. They can kill the conversation before it even starts.

Fix: Ask open-ended questions that invite storytelling or opinion-sharing. These questions start with “what,” “how,” or “why” and encourage the other person to engage.

Example:

“What’s your go-to coffee order? I’m always looking for new recommendations!”

6. Being Negative or Complaining

Mistake: “Ugh, today was such a long day. Hope yours was better.”

Starting with negativity can drag the conversation down before it even begins. It can also make the other person feel like they need to “fix” your mood, which isn’t a great way to start a connection.

Fix: Keep the tone light and positive. Focus on shared experiences or something you both enjoyed from your encounter.

Example:

“That workshop was so inspiring! What was your favorite part?”

7. Ignoring the Context of Your Encounter

Mistake: Sending a message that doesn’t reference your real-life interaction.

If you met someone at a book club, a coworking space, or a local event, ignoring that context can make your message feel random or impersonal. It’s like meeting someone at a party and then texting them about the weather—it doesn’t make sense.

Fix: Always tie your message back to where or how you met. It shows you were present in the moment and makes the conversation feel more natural.

Example:

“I’m still thinking about that debate we had at the book club last night! What did you think of the ending?”

8. Trying Too Hard to Be Funny

Mistake: “I’d say it’s nice to meet you, but I already know you’re trouble.”

Humor is subjective, and what’s funny to you might not land with the other person. Forced jokes can come across as awkward or even off-putting, especially in a first message.

Fix: If humor comes naturally, go for it—but don’t force it. A lighthearted comment or a playful observation is often enough to keep things fun without overdoing it.

Example:

“I think we were the only two people at that event who weren’t taking notes. Were you also just there for the free snacks?”

9. Overthinking or Over-Editing

Mistake: Spending 20 minutes crafting the “perfect” message.

Overthinking can lead to messages that feel stiff, rehearsed, or inauthentic. It can also make you second-guess yourself, which might prevent you from hitting send at all.

Fix: Trust your instincts. Write something that feels natural and send it. Remember, the goal is to start a conversation, not to impress with perfection.

Example:

“I saw you at the farmers market earlier—what’s your favorite thing to pick up there?”

10. Not Having a Clear Call to Action

Mistake: Ending the message without giving the other person an easy way to respond.

A message that trails off without a clear question or invitation can leave the other person unsure of how to reply. It’s like ending a conversation in person with “Well… I guess I’ll see you around.”

Fix: End with a question or a clear next step. It could be as simple as asking for their opinion, sharing a recommendation, or suggesting a low-pressure way to continue the conversation.

Example:

“I’m thinking of checking out that new exhibit at the museum. Have you been?”

Why First Messages Matter in Proximity-Based Social Apps

Proximity-based social apps like Matuvu are designed to help you reconnect with people you’ve already crossed paths with in real life. Unlike traditional social media or dating apps, the focus is on real-life interactions and letting connections evolve naturally. That’s why the first message is so important—it’s your chance to build on the moment you shared, whether it was a brief smile, a shared laugh, or a passing conversation.

Matuvu’s minimal profile design (just one photo, no bio, no name) keeps the focus on the encounter itself, not on curated profiles or algorithms. This means your first message carries even more weight. It’s not about impressing someone with your credentials or looks—it’s about sparking a genuine conversation based on the real world.

How to Craft a Great First Message

Now that you know what to avoid, here’s how to craft a first message that invites a response:

Be specific. Reference something from your real-life encounter to show you were paying attention.
Keep it short. Aim for 1-2 sentences that are easy to respond to.
Be authentic. Write like you’re talking to a friend, not delivering a performance.
Ask open-ended questions. Give the other person room to share something meaningful.
End with a clear call to action. Make it easy for them to reply by ending with a question or invitation.

Examples of Great First Messages

Here are a few examples to inspire you, based on different real-life scenarios:

At a café:

“I couldn’t help but notice your sketchbook earlier—are you an artist? I’d love to hear more about what you were working on.”
At a coworking space:

“I saw you working on that coding project earlier. What got you into [specific programming language]?”
At a local event:

“That was such a great discussion at the meetup! What inspired you to start [topic they mentioned]?”
While commuting:

“I think we take the same bus route—what’s your favorite podcast to listen to on the way?”

What to Do If the Conversation Stalls

Even with the best first message, conversations don’t always flow perfectly. If you find yourself stuck, try one of these strategies:

Share something about yourself. Sometimes, the other person might be unsure how to respond. Giving them a little more to work with can help.

“I’ve been getting into urban gardening lately—it’s been so rewarding to grow my own herbs. Do you have any hobbies you’re passionate about?”
Ask a follow-up question. If their response was short, dig a little deeper.

“You mentioned you love hiking—what’s your favorite trail around here?”
Suggest a low-pressure next step. If the conversation feels natural, you might invite them to continue it in person.

“There’s a great bookstore downtown that just opened—want to check it out this weekend?”

The Power of Real-Life Encounters

Real-life interactions have a magic that digital-only connections often lack. There’s something special about meeting someone in person, whether it’s at a café, a local event, or even just passing by on the street. These encounters can lead to friendships, affinities, or collaborations—but only if you take the next step to follow up.

That’s where Matuvu comes in. As a proximity-based social app, Matuvu helps you reconnect with people you’ve already seen, making it easier to turn those fleeting moments into meaningful connections. Whether you’re new to a city, looking to expand your social circle, or just want to make the most of everyday encounters, Matuvu provides a simple, ethical way to follow up.

Ready to Start Connecting?

If you’re tired of generic social apps and want a tool that focuses on real-life interactions, give Matuvu a try. It’s designed to be simple, human, and respectful of your privacy—no algorithms, no swiping, and no pressure. Just real people, real encounters, and the chance to see where a conversation might lead.

Download Matuvu today and start turning those everyday moments into meaningful connections:

Final Thoughts

The first message is your opportunity to build on a real-life encounter and turn it into something more. By avoiding these common mistakes and focusing on authenticity, specificity, and warmth, you’ll give yourself the best chance of sparking a conversation that feels natural and engaging.

Remember, the goal isn’t to craft the “perfect” message—it’s to start a conversation that reflects the real you. So take a deep breath, trust your instincts, and hit send. You never know where it might lead.