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Conversation Starters with a Guy

by eharmony Editorial Team - November 22, 2023

Reaching out to text someone on a dating app can be a nerve-racking experience, particularly for straight women, who can feel bound by an outdated expectation to let guys make the first move. But for those bold enough to start a conversation with a guy online, particularly when it’s the right guy, the rewards are there. So let’s look at how you can get things started.   

While these tips are generally good for any gender identity or sexuality, let’s take a look at some historically effective conversation starters with a guy and how we can make these work in online dating.   

Making the first move is the new dating culture

We live in a world with rapidly changing gender roles and a spectrum of identities and sexualities. So making the first move  doesn’t carry the same weight of baggage it used to. You may even find you get better-quality dates, not to mention the positive feeling that you’re in control of your dating life.  

Don’t be afraid to use some flirty conversation starters over text with a guy, be a bit forward or make a funny joke to get the ball rolling. A study by MIT and the University of Chicago recently found that women who make the first move on dating apps experience a response rate of 60%1, with men sitting at 35%.   

Some good conversation topics for texting a guy

When looking for general conversation starters with a guy, try focusing on them in the opening message and then expand into your commonalities.  

Here are some examples of topics and messages to consider:  

Hobbies and interests

This is one of the most common conversation topics with a guy and shows them you’ve taken an interest. 

  •  “I see you like carpentry.  Are you working on anything right now?”  

Culture and entertainment 

Having tastes in common is a good starting point and it can be interesting to see where a guy’s cultural tastes lie.  

  • “So Charlie Puth is your favorite artist? Did you go to his show last month?” 
  • “Which celebrity has completely lost your respect?” 

Goals and dreams

People are very connected to their ambitions and vision for their future. 

  • “If you could start over, would you still work in the same industry?” 
  • “What long shot have you recently taken that paid off?” 


This doesn’t apply to everyone but most people have some interest in getting away from home now and then. 

  • “Do you prefer active holidays or just relaxing by the beach?”  
  • “What would be your dream holiday destination if money were no object?”  

City life

Discussing some local interests is always one of the sure-fire conversation starters with a guy.    

  • “What place in the city do you think makes the best pizza?” 

Interesting questions to start a conversation with a guy

Questions in your dating app’s messaging system are the easiest way to start a conversation and keep it going as you explore the potential of your connection. Go for open-ended questions that allow room for the conversation to grow while keeping it focused on shared connections.   

Personal questions

Few people can resist the opportunity to talk about themselves now and again. And as long as it’s not too intrusive, it’s fine to ask people about their backgrounds. Questions such as:.  

  •  “So you live in San Diego but you’re from Knoxville. What was your childhood like?” 
  • “How adventurous are you?”  

Deeper questions

Similar to personal questions, these work because they interact with someone’s values and experiences. 

  • “What’s one thing your life feels empty without?” 
  • “Do you think morality is something we’re born with or learn as we develop?” 

Thought-provoking questions

These conversation starters with a guy are interesting because they often elicit an unpredictable response. 

  • “Considering we’re on a dating app, what do you think is the role technology is playing in our society? Progress or making everything worse? 

Random questions

These can help you stand out and be the starting point for an entertaining exchange.  

  • “What should we name the first colony in space?”  
  • “If you could live in one movie’s world, which one would it be?”  

Fun questions

Sometimes people just want to have a nice, light-hearted interaction to see if you have conversational chemistry.  

  • “Which TV show quotes do you overuse in real life?” 
  • “The last thing you ate is all you can eat from now on. How long would you survive?” 

Using conversation starters with a guy to build something real

While these should serve as alaunching-off point for good conversation starters with a guy, always try to assess the best approach on an individual basis. Some people might not understand random questions or might not give much thought to travel. So adapt them to incorporate how you imagine your personalities fit. 

Remember, when looking at how to start a conversation on a dating app, it should be fun, engaging and mutually focused on your relationship goals. But practice makes perfect. So why not come practise your opening lines while meeting interesting compatible eligible singles on eharmony? Register now.   

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