That moment after matching with someone you're interested in—then realizing you need to actually start the conversation—can be nerve-wracking. What do you say? How do stand out without being weird? The good news: crafting a great first message is easier than you think when you know what works.
Why Most First Messages Fail
Before we dive into what works, let's talk about what doesn't. Generic openers like "Hey" or "Hi" get low response rates because they're forgettable. Copy-paste pickup lines feel insincere. And overly aggressive or sexual messages right off the bat? Those get deleted immediately.
The goal of a first message is simple: start a conversation that makes the other person want to reply. That means being interesting, showing you've actually looked at their profile, and giving them something easy to respond to.
The Profile Reference Method
This is the gold standard. Reference something specific from their profile—a hobby, photo, or bio detail—and ask a question about it. This shows you're genuinely interested in them as a person, not just casting a wide net.
Examples:
- "I see you're into hiking—have you ever done the trails around Lake Como? It's stunning this time of year."
- "Your photo at the Duomo is incredible! What's your favorite hidden gem in Milan?"
- "You mentioned you love Italian cinema—any recent films you'd recommend?"
The Shared Experience Opener
Since you're both in Milan, reference local experiences. Talk about the city, events, or neighborhoods. This creates immediate common ground.
Examples:
- "I was just walking through Navigli and thought how perfect this weather is for an aperitivo. Do you have a favorite spot?"
- "Have you tried the new exhibit at the Museo del Novecento? Thinking of checking it out this weekend."
- "What's your take on Milan's brunch scene? I'm still searching for the perfect place."
The Lighthearted Question
Fun, low-stakes questions are easy to answer and reveal personality. Avoid deeply personal questions early on—stick to topics like food, travel, music, or weekend habits.
Examples:
- "If you could eat only one Milanese dish for the rest of your life, what would it be?"
- "What's the best concert you've been to recently?"
- "Coffee or aperitivo—what's your go-to for a first date?"
The Humor Approach (Use Carefully)
A well-placed, gentle joke can be charming, but humor is subjective. Avoid sarcasm or anything that could be misinterpreted. If you do try humor, make it light and self-deprecating if possible.
Example: "I'm terrible at first messages, but I figure being straightforward is better than overthinking it. So hi, I'm [name] and I promise I'm more interesting than this opening line."
Timing Matters
Send your message when you're likely to get a response. Weekday evenings (7-10pm) and weekend afternoons tend to be active times on dating apps. Avoid Monday mornings or Friday nights when people are busy or out.
What NOT to Include
- Compliments about physical appearance—save those for later. Comment on something they've chosen to showcase (style, photo composition, etc.) if you must.
- Sexual or suggestive comments—never appropriate for a first message.
- Interrogation-style questions—don't rapid-fire questions. Ask one, wait for a response.
- Negging or backhanded compliments—these are manipulative and don't work on people worth dating.
Putting It All Together
The best first messages are personalized, show you've read their profile, ask an engaging question, and are concise. Here's a formula:
Greeting + Profile reference + Question
Example: "Hi [Name], I noticed you're a photographer—your shots of Milan are gorgeous! What's your favorite spot to capture in the city?"
When They Don't Reply
Don't take it personally. People are busy, may have paused using the app, or simply aren't feeling a connection. If they don't respond after a week or so, it's okay to move on. Persistence is not attractive—respect their space.