Because, if we’re being honest, you probably don’t have a genuine interest in how their workday went—right?
Struggling to break the ice when messaging women on a dating site? Figuring out what to talk about with someone you just met online can feel intimidating, especially when you want to stand out from the crowd. The truth is, good conversation starters for online dating can make all the difference in creating a connection.
As a psychotherapist specializing in relationships, I’ve seen firsthand how the right opening message can set the tone for a genuine interaction. That’s why the online dating conversation starters in this article are designed to help you make a memorable first impression, spark curiosity, and create a natural flow of communication—giving you the best chance of forming a meaningful connection.
What can you mention at the beginning of a conversation? If we’re talking about the most straightforward but catching conversation starters for online dating, a good opportunity to approach a woman is by describing yourself first.
Start with specifying your strong sides that you’re proud of, and share your feelings, intentions, and expectations for your relationship. Respond to her about your achievements, interesting hobbies, or last journeys to catch her attention and show your worth. Some of the conversation starters dating examples you’ll find below:
💡 One common mistake in online dating topics is being too vague. Women are drawn to authenticity and specifics. Instead of just saying, “I’ve been to 15 countries,” share why travel excites you—adventure, culture, or personal growth? Connecting experiences to your personality makes you more memorable.
Asking for advice is one of the most effective dating sites conversation starters. You can get the attention of a preferred woman by asking what she thinks about a certain topic. By doing this, you’ll demonstrate your readiness to engage in conversation by placing value on her opinion. The following online dating conversation topics will help you:
💡 Asking for advice isn’t just a great conversation starter—it taps into the Ben Franklin Effect, which makes someone feel more invested in you. In my experience, men who genuinely seek a woman’s opinion create mutual respect and engagement. It also signals confidence and helps you stand out from generic small talk.
In my years of working with individuals interested in online dating, one of the most common frustrations I hear is that many men feel like they’re doing everything right but still struggle to make connections. The truth is, online dating isn’t just about sending messages—it’s about how you communicate, the energy you bring, and whether you create a real sense of connection.
Look at my top tips for improving your communication skills and making sure your messages stand out—so you can confidently build meaningful connections.
Instead of the overused “Hey, how’s your day?” try asking something that shows you’ve actually paid attention to their profile. This makes the other person feel seen and valued.
✅ Example: “I saw that you love hiking! What’s the most breathtaking trail you’ve ever been on?”
Why it works: People enjoy talking about their passions, and this invites them to share something meaningful, which leads to a deeper conversation.
Rather than only asking questions, share a little about yourself to create balance in the conversation. Vulnerability (even in small doses) can encourage openness from the other person.
✅ Example: “I just got back from trying sushi for the first time—why did I wait so long?! What’s a food or experience you’ve been meaning to try?”
Why it works: Self-disclosure builds trust and gives the other person a chance to connect with you through shared experiences or curiosity.
A common complaint I hear from men is, “Girls don’t like me online, but they laugh at my jokes in real life.” The reason? Online conversations can feel stiff or forced, which makes humor an important tool for breaking the ice.
✅ Example: “So, important question: Would you rather have a pet dinosaur or a pet dragon? There’s a right answer, and I need to know where you stand.”
Why it works: Humor creates positive emotions and makes you more memorable and approachable.
One of the biggest mistakes people make in online dating is not matching the tone of the other person’s messages. If someone responds enthusiastically, mirror that energy. If they reply with shorter, more reserved messages, ease into deeper conversation gradually.
✅ Example: If they reply with a short response like “Yeah, I like traveling,” instead of bombarding them with more questions, try: “That’s awesome! What’s one trip that really stands out to you?”
Why it works: This keeps the conversation flowing without overwhelming the other person.
Instead of generic praise like “You’re beautiful,” which they’ve likely heard countless times, focus on something unique about them.
✅ Example: “Your profile says you play the guitar—what’s your favorite song to perform?”
Why it works: Compliments that highlight personality, skills, or passions are far more meaningful and lead to deeper conversations.
If you sense a good back-and-forth, guide the conversation toward a natural next step. This keeps momentum going rather than letting the chat fizzle out.
✅ Example: “I love this convo about travel! Want to trade bucket list destinations?”
Why it works: Open-ended prompts invite them to continue rather than leaving them unsure of how to respond.
If you are wondering how to start a conversation on dating sites and get a good response rate, show your interest in a woman you really like by asking questions about her profile. Usually, you can find a lot of information in a typical online dating profile. Dating conversation examples based on this data may look like this:
💡 As a psychotherapist, I’ve seen how personal questions based on someone’s profile can instantly create a sense of connection. When you show genuine curiosity, it signals that you’re paying attention—not just sending generic messages. In my experience, people respond more openly when they feel valued.
Posing questions that require some storytelling is a good online dating start conversation method. For instance, it can be a perfect approach to encourage a discussion with women and let them express their thoughts, even if you already know the answer to your inquiry. Here you can find some of the best conversation starters for online dating:
The first questions to ask on dating apps can be connected with the women’s reasons for using online dating services. Show an interest and ask about her dating goals and intentions, preferences concerning her future partner, etc. If you are a beginner in online dating and wondering how to start a conversation, see the following examples:
💡 Clarifying intentions early builds trust and prevents mismatched expectations. My clients often feel lost in dating due to unclear goals—these questions show confidence and create meaningful connections from the start.
Finally, the chatting format for dating implies you have to become closer to your potential partner. That is why we suggest starting a conversation by discussing your short-term and long-term plans, dreams, and ambitions. This section will describe some more things to talk about online dating:
In my work as a psychotherapist, I’ve counseled many individuals and couples who struggled with online conversations—sometimes before they even became couples. One common challenge I’ve seen is the fear of saying the “wrong” thing, leading to hesitation or generic messages that don’t spark interest. Many clients tell me that they freeze when faced with a blank chat window and spend too much time analyzing every word instead of just communicating naturally.
One client, for example, kept sending dry, one-word messages because he feared coming off as “too much.” When we worked together, I encouraged him to ask open-ended questions and share small personal details. Almost immediately, his conversations became more engaging.
📍 The truth is, online dating isn’t just about finding the right match—it’s about learning how to communicate in a way that invites curiosity and keeps a conversation flowing. When I coach clients, I remind them that a great first message isn’t about impressing someone; it’s about creating an opportunity for connection.
I hope these conversation starters for online dating help you break the ice and spark meaningful connections. As a psychotherapist, I’ve found that successful conversations combine curiosity with authenticity. Try different approaches to see what feels most natural—after all, the goal isn’t just a reply, but a genuine and enjoyable exchange.
You can study and practice communication skills, as well as listening strategies and tactics by using online resources and platforms like MindTools, TED, or Coursera.
Yes, you will get a higher reply rate if you learn about the person from their profile first, and then use this information in your first messages. This way, you’ll show that you’re truly interested in a person.
To continue the conversation, it is advisable to find common ground, show interest in the woman you’re chatting with, ask her follow-up questions, and in general manifest your positive attitude and sense of humor.
Make sure the woman you initiate the contact with has similar dating goals and preferences, give yourself time to prepare, be honest, and show your real intentions. Having an attractive profile will boost your confidence as well.
Stay away from offensive jokes and do not pretend to be anyone else if you don’t want to spoil the first impression. Avoid being too self-confident, obsessive, or superior, instead of keeping things moving slowly.
