PDF download Download Article
Friendly, in-depth, flirty—talk to any guy in style
PDF download Download Article

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

PDF download Download Article
  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?
  2. Advertisement
2

Funny Stories

PDF download Download Article
  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 543 wikiHow readers who've struggled with conversation, and 63% of them agreed the best way topic is something positive. [Take Poll]
9

Family and Friends

PDF download Download Article
10

Love and Relationships

PDF download Download Article
12

Social Media

PDF download Download Article
  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?

Expert Q&A

Ask a Question
200 characters left
Include your email address to get a message when this question is answered.
Submit
Advertisement

Video

Tips

Submit a Tip
All tip submissions are carefully reviewed before being published
Name
Please provide your name and last initial
Thanks for submitting a tip for review!
Advertisement

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]


Advertisement

You Might Also Like

What Topics Should You Talk About with a Girl16 Awesome Topics to Talk About with a Girl
Come Up with Good Conversation TopicsCome Up with Good Conversation Topics
What to Talk About on a First Date50 First Date Conversation Starters to Spark a Connection
Good First Date Questions75+ First Date Questions to Connect & Make a Good Impression
Best Conversation Starters165 Best Conversation Starters: Funny, Deep, Flirty & More
Questions to Ask Someone You Just Met100+ Questions to Help You Get to Know Someone You Just Met
Questions to Ask a Guy Before DatingLearn More About Your Next BF By Asking Him These Questions
Start a Good ConversationStart a Good Conversation
Continue a Conversation with a Boy over Text15 Ideas to Maintain a Flirty & Sweet Text Convo With a Boy
Questions to Ask on Tinder170 Funny & Fascinating Questions to Ask Your Tinder Match
Ask Me Anything QuestionsAsk Me Anything Questions: 340+ Funny, Deep, & Random Ideas
Become Best Friends with a Guy over TextBecome Best Friends with a Guy over Text
Win a Man's Heart OnlineWin a Man's Heart Online
Speed Dating QuestionsSpeed Dating Questions: The Best Prompts for an Instant Connection
Advertisement

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 179,868 times.
62 votes - 74%
Co-authors: 5
Updated: July 27, 2025
Views: 179,868
Categories: Social Interactions
Thanks to all authors for creating a page that has been read 179,868 times.

Did this article help you?

Advertisement