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Friendly, in-depth, flirty—talk to any guy in style
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Let’s face it—starting a conversation with a guy you’ve just met or don’t know very well can seem really intimidating. You want to have a fun and engaging conversation that keeps a guy interested and avoids any awkwardness. So where do you start? Fortunately, there are so many different conversation starters for you to choose from. Here’s a list of the best talking points for a meaningful conversation with a guy that’ll leave you feeling confident and ready to start chatting!

Interesting Topics to Talk About

  1. Learn more about a guy's passions by asking about his hobbies and interests.
  2. Share a funny story to connect with him.
  3. Ask him what his favorite restaurant or meal is.
  4. Inquire about what he studies, does for a living, or aspires to do.
  5. Give him a chance to open up about his loved ones.
1

Hobbies and Interests

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  1. Let’s face it, we all enjoy talking about ourselves. Ease into the conversation by asking him about his interests. You might end up having some shared hobbies to bond over![1] Here are a few questions to get you started:
    • What are some fun facts about yourself?
    • What do you like to do in your free time?
    • What hobbies have you always wanted to try?
    • What is your favorite sport?
    • Do you have any hidden talents?
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2

Funny Stories

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  1. Laughter can be a great way to connect with people and relieve tension. Try telling him a joke or sharing a funny story. If he doesn’t find it funny, don’t be discouraged.[2] Keep the conversation going by asking him what he does find funny. You could ask:
    • What’s the funniest thing that’s ever happened to you?
    • What’s your favorite joke?
    • Do you have a favorite comedian?
    • What are some videos or memes that make you laugh?
    • What is the funniest text you’ve ever gotten or sent?
    • Reader Poll: We asked 520 wikiHow readers who've struggled with conversation, and 63% of them agreed the best way topic is something positive. [Take Poll]
3

Entertainment and Pop-Culture

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  1. Pick his brain about what types of movies he loves to watch or the type of music he likes to listen to. You might just get a great movie recommendation or find your new favorite song. Pick his brain by asking him:
    • What’s the best book you’ve ever read?
    • What show are you currently binge-watching?
    • Who’s your favorite actor or actress?
    • What’s your most listened to song?
    • What band would you love to see live?
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  1. Chances are, the guy you’re talking to has places he really wants to see or explore. Find out by sharing travel bucket lists or learning about a country he’s been dying to visit. Try asking:
    • What are some places you’d love to visit one day?
    • What is the best trip you’ve ever taken?
    • Do you prefer flying or going on a road trip?
    • What would your dream vacation look like?
    • How often do you travel?
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6

Pets and Animals

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  1. Even if the guy you’re talking to doesn’t have a pet, asking him about his favorite animal or dream pet is a great way to get to know him. If you have a pet yourself, you could also share a picture to start the conversation.[4] For instance, ask:
    • Do you own any pets?
    • What is your spirit animal?
    • Are you a dog or cat person?
    • Did you have any pets when you were growing up?
    • If you could have any animal as a pet, what would it be?
7

Career and Education

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  1. Ask the guy you’re talking to what he does for a living or what he studies. This can be a great conversation starter and also help you learn more about his daily life. Here are a few questions you can ask:
    • What does your typical day look like?
    • What is your dream job?
    • What was (or is) your favorite class?
    • What was your first job?
    • What types of skills does your career require?
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9

Family and Friends

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  1. Giving him a chance to talk about the people that are important to him will allow him to lead the conversation. If you both know someone in common, you can both talk about that person, especially if they were the one that introduced you to the guy.[5] Get the conversation rolling by asking:
    • What’s your family like?
    • Do you have any siblings?
    • How often do you see your family?
    • Do you have a close friend group?
    • Who is the closest person to you in your life?
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10

Love and Relationships

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  1. Let’s be honest, if you are interested in the guy you are talking to, you are probably curious about his dating life.[6] Even if he’s already in a relationship or you just want to be friends, talking about his love life is a great way to share something heartfelt and meaningful. Start the conversation by asking:
    • Are you seeing anyone romantically?
    • What do you look for in a relationship?
    • What was your first date like?
    • What qualities do you find attractive in a partner?
    • What are your relationship deal breakers?
11

Compliments

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  1. Just like girls, guys also love receiving compliments.[7] In fact, complimenting him can be a great conversation starter and make him feel like you were paying close attention to him. Here are good examples of the types of compliments you can give:
    • “I love your fashion sense or style.”
    • “You have a really nice smile.”
    • “You have a great sense of humor.”
    • “Great job on your presentation today.”
    • “You have excellent taste in movies.”
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12

Social Media

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  1. Even if you don't have a heavy social media presence, we all have that one social media platform that we can’t get enough of or just spend too much time on. You may have even met or built a relationship with the guy you’re talking to online.[8] Here are some questions to get the conversation started:
    • What is your favorite or most visited social media site?
    • Do you spend a lot of time on social media?
    • Have you seen this meme or funny video?
    • What is your least favorite social media platform?
    • Do you prefer online or real life interactions?
13

Zodiac Signs

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  1. Whether he knows all about his zodiac sign or has no clue about astrology, this topic could spark a really fun conversation.[9] Try asking him:
    • Do you know what your zodiac sign is?
    • Do you believe in horoscopes?
    • What is your birthday or birth month?
    • What are the common traits of your zodiac sign?
    • Do you know what element (water, air, earth, or fire) rules your zodiac sign?[10]
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15

About Yourself

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  1. Talking about yourself will give him the chance to get to know you better and make him feel more comfortable to open up to you.[11]
    • Talk about your favorite hobbies or what you like to do in your free time.
    • Discuss your profession or career and what you like about it.
    • Give him some good movie or book recommendations.
    • Share some memorable childhood stories.
    • Talk about places on your travel bucket list
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Warnings

  • Avoid asking too many questions at once. The last thing you want in a conversation is to feel like you’re in the hot seat or being interrogated.[13]


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About This Article

Maria Avgitidis
Co-authored by:
Matchmaker & Dating Expert
This article was co-authored by Maria Avgitidis and by wikiHow staff writer, Donna Sarkar. Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist. This article has been viewed 175,974 times.
61 votes - 75%
Co-authors: 5
Updated: July 27, 2025
Views: 175,974
Categories: Social Interactions
Thanks to all authors for creating a page that has been read 175,974 times.

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