That moment when you find someone interesting—their profile catches your eye, they seem like someone you'd enjoy meeting—but then you freeze. What do you say? How do you start a conversation that doesn't end in silence? You're not alone. Crafting the perfect first message is a common challenge, but it doesn't have to be.
The good news: there's a science to great openers, and it's simpler than you think. Let's explore what works, what doesn't, and how you can start conversations that actually lead somewhere.
The Problem with "Hey"
We need to address the elephant in the room: "Hey" or "Hi" are among the worst first messages you can send. They're not necessarily bad because they're boring—though they certainly are—but because they place the entire burden of continuing the conversation on the other person.
When someone receives just "hey," they have to figure out how to respond, what to say, and whether you're actually interested or just mass-messaging. Most of the time, the answer is to ignore and move on.
Your first message should do three things:
- Show you've actually looked at their profile
- Give them something easy to respond to
- Stand out from the dozens of other messages they've received
The Profile Reference Formula
The most effective first messages reference something specific from the person's profile. This demonstrates genuine interest and gives them an obvious way to respond. Here's a simple formula:
Observation + Question = Engaging opener
For example:
- "Your photo at the Chicago Jazz Festival looks amazing! What was your favorite performance that day?"
- "I see you're into hiking—have you explored the trails at Starved Rock yet?"
- "Your dog in that picture is adorable! What's their name and breed?"
Notice how each opener:
- References something specific from their profile
- Asks an easy-to-answer question
- Shows you paid attention
Chicago-Specific Conversation Starters
When both of you are in Chicago, the city itself offers endless conversation material. Use local context to your advantage:
- Neighborhood talk: "I see you're in Lakeview—do you have a favorite brunch spot around there?"
- Chicago sports: "Are you a Cubs or White Sox fan? Just realized I don't know any Bears fans this season!"
- Local events: "Did you go to Lollapalooza last summer? Thinking about going this year."
- Weather bonding: "How are you surviving this Chicago winter? Ready for lakefront season yet?"
Local references create instant common ground and show you're genuinely part of the Chicago community.
Humor Works—When Done Right
A well-placed joke or light-hearted observation can make you memorable, but humor is subjective. If you're going to try being funny:
- Keep it light and positive
- Avoid sarcasm or negative humor early on
- Self-deprecating humor often works well
- Don't force it—authenticity is more important
Example of good humor: "I have to confess—I'm terrible at first messages, so I'm going with 'hi' followed by this slightly more creative follow-up. How's that for effort?"
Avoid cheesy pickup lines or anything that could come across as insincere.
Questions That Spark Real Conversation
Some questions are better than others. Here's a breakdown:
Great Questions (Ask These)
- "What's the last thing that made you laugh really hard?"
- "If you could have dinner with anyone, living or dead, who would it be?"
- "What's something you're really passionate about?"
- "What's your favorite way to spend a weekend in Chicago?"
- "What's the best concert you've ever been to?"
Questions to Avoid
- "What do you do for work?" (save for later—it's fine but not exciting)
- "Why are you single?" (never ask this)
- Anything overly personal or invasive
- Yes/no questions (they end conversations)
Timing Matters
When you send your message can affect response rates. Research suggests:
- Weekday evenings (6-9 PM) are often best—people are relaxed and checking messages
- Weekend afternoons also see good engagement
- Early mornings and late nights tend to have lower response rates
That said, don't overthink timing. A great message at 2 PM can still get a response. Consistency matters more than perfect timing.
What NOT to Do
Let's cover the mistakes that get messages deleted immediately:
- Generic compliments: "You're beautiful/handsome" is nice but doesn't start a conversation.
- Sexual comments: Never lead with this. It's inappropriate and shows lack of respect.
- Negging (backhanded compliments): "You're pretty for your age" is not a compliment.
- Copy-pasting the same message to everyone: People can tell, and it's obvious you're not interested in them specifically.
- Asking why they're on the platform: "What are you looking for here?" is a fine question but not as first message material.
If They Don't Respond
Even the perfect first message sometimes goes unanswered. Don't take it personally. Reasons could include:
- They're not actively using the app
- They're overwhelmed with messages
- They're not interested (and that's okay!)
- They simply missed your message
If you've sent a thoughtful opener and get no response after a week or so, it's fine to move on. Don't send follow-up messages asking why they didn't reply. It comes across as needy and can feel pressured.
Focus your energy on people who are engaged and reciprocate interest.
Practice Makes Perfect
Like any skill, crafting great first messages improves with practice. Start by sending thoughtful openers to profiles that genuinely interest you. Even if not every conversation leads somewhere, you'll learn what works for your style and voice.
Remember, the goal isn't to impress everyone—it's to find people you actually connect with. Authenticity always beats a perfectly crafted but insincere message.
Conclusion
The perfect first message is one that's genuine, shows you've paid attention, and gives them an easy way to respond. Reference their profile, ask an open-ended question, be yourself. That's the formula that gets replies and starts real conversations.
Now that you know how to start conversations, it's time to put it into practice.