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I’ve been in a similar situation before, and I know how it feels when you’re trying to have a conversation with someone, and you suddenly find yourself at a loss for words. This can be especially true when trying to chat with someone of the opposite gender. 

Starting a conversation can be tough, whether you’re on a first date or just trying to get to know someone better. Even the best of us can struggle with small talk. 

However, knowing a few key topics can make all the difference in building rapport and uncovering shared interests. 

So let’s talk about some ways to break the ice and get the conversation flowing. With these conversation starters, you’ll never run out of things to say, and you might even discover a deeper connection with the person you’re talking to.

1. Tell Him an Interesting Story About Yourself 

Telling a personal story or anecdote can be a powerful way to evoke emotions, illustrate a point, or simply entertain your conversation partner. When sharing a story, think about the context and choose a tale that is relevant, interesting, or relatable. 

Try not to sound boring. You can share a funny incident from your childhood, a memorable travel experience, or a touching moment that had a profound impact on your life. Stories like these are incredibly interesting.

As you tell your story, be mindful of the pacing, tone, and details, and try to paint a vivid picture with your words. It will help your listener become immersed in the narrative and form a stronger emotional connection with you. 

Encourage him to share his own stories, too, to create a sense of mutual trust and openness, allowing both of you to learn more about each other’s experiences and perspectives.

2. Hobbies and Interests

Starting a conversation by discussing hobbies and interests can be a winning strategy for many reasons. Firstly, people typically enjoy talking about their passions, which can help create a positive and engaging atmosphere. 

Besides, it provides an opportunity to discover common ground and shared interests that can strengthen your connection. Inquire about his favorite pastimes, recent accomplishments, or what he’s looking forward to in the future. 

Also, listen actively and ask follow-up questions to encourage him to share more about himself, while also sharing your own experiences in a balanced manner.

[Related: How to Have Better Conversations With Friends]

3. Travel and Adventure

Travel is a topic that can lead to captivating stories and provide a window into a person’s values, interests, and life experiences. Engaging in conversations about travel can help you learn more about the guy’s perspective on different cultures, environments, and ways of life. 

Ask about his favorite destinations, memorable trips, or dream vacations. Share your own travel stories and discuss what you both love about exploring new places. 

As you delve into the topic of travel and adventure, you may find that it sparks intriguing conversations about personal growth, history, and world events, all of which can deepen your connection and understanding of one another.

4. The Story Behind His Name

For instance, some people have names that reflect their family’s cultural heritage, while others may be named after a historical figure or a beloved relative.

Inquiring about the story or meaning behind someone’s name can lead to fascinating insights into their family history, cultural background, or personal identity. 

Inquire if his name has a special meaning or significance, if he was named after someone, or if there are any interesting stories associated with his name. 

Asking about his name can spark discussions about ancestry, traditions, or even the unique characteristics that his name represents. It also shows that you’re genuinely interested in getting to know him on a deeper level. 

Be sure to share the story behind your own name as well.

[Read: The 12 Best Hinge Conversation Starters]

5. What He Values in a Partner

Inquiring about what he values most in a woman or a partner can lead to meaningful discussions about the qualities and characteristics that are important to him in a relationship. 

You might ask about his thoughts on trust, communication, shared interests, or emotional support. You could inquire whether he values a strong intellectual connection, a shared sense of humor, or a partner who is adventurous and open to new experiences.

Sharing ideas about your preferences, whether similar or different can develop a deeper understanding of what each of you is looking for in a relationship. 

This conversation can also help to clarify any potential compatibility or areas where you might need to compromise or work together to grow as a couple.

6. Career and Ambitions

Talking about career and ambitions can be an excellent way to gauge a person’s goals, values, and work ethic. Ask about his current job, past experiences, or future aspirations. 

This can open up discussions about the challenges and successes he’s faced, as well as provide insight into his motivations and passions. 

When discussing career-related topics, be mindful to keep the conversation light and engaging rather than overly serious or heavy. Remember, the goal is to connect and understand each other better, not to conduct a job interview.

[Also read: How to Start a Conversation With Anyone]

7. Pop Culture and Entertainment

Pop culture and entertainment can be a treasure trove of conversation topics that appeal to a wide range of interests. Movies, TV shows, books, music, and even video games can provide endless fodder for enjoyable discussions. 

What he’s currently watching, reading, or listening to? Find out and share your own favorites as well. This can inspire lighthearted debates, recommendations, or even plans for future activities such as movie nights or book clubs. 

8. Current Events and World Issues

Having conversations about current events and world issues can be a great way to know his level of intellectual curiosity and critical thinking skills. 

While it’s important to approach this topic with sensitivity and respect, engaging in thoughtful conversations about important issues can help you understand each other’s perspectives, values, and beliefs. 

Be open to considering different viewpoints and aim to create a space where you can exchange ideas without judgment. By doing so, you’ll foster a deeper connection and appreciation for the unique qualities each of you brings to the conversation.

[Interesting: 70 Flirty Jokes and Pick Up Lines to Make Your Crush Laugh]

9. Personal Growth and Self-Improvement

Exploring personal growth and self-improvement can lead to insightful and thought-provoking conversations that help you understand a person’s values and motivations. 

You might discuss recent personal achievements, challenges overcome, or self-improvement goals. For instance, you could ask about any new skills or habits he’s been working on, like learning a new language or adopting a healthier lifestyle. 

10. Discuss a Shared Movie Experience

So, let’s say you both recently watched the same movie, like an action-packed blockbuster or a critically acclaimed drama. 

You could kick off the conversation by asking what he thought about the film, his favorite scenes, or any particular aspects that stood out to him. You might say, “I just loved the plot twist in that movie we saw last week! What did you think of it?”

Or you could just ask him about his best movies and pick one that you’ve also watched to discuss with him.  As you chat about the movie, you can also delve into deeper topics like the themes, underlying messages, or even the social and cultural implications it presents. 

This can lead to engaging discussions that reveal your perspectives on life, society, and art. Remember to keep the tone conversational and light-hearted; after all, you’re discussing a shared experience that you both enjoyed.

[Related: How to Never Run Out of Things to Say in Conversation]

11. Family and Friends

Diving into the topic of family and friends can provide a glimpse into a person’s upbringing, values, and the people who have shaped their life. 

Engaging in conversations about family and friends can help you both find common ground and develop a deeper understanding of each other’s personal history and support systems.

You can ask him about his family traditions, memorable experiences with friends, or lessons learned from loved ones. For example, you could ask about his relationship with his siblings or the best advice he’s ever received from a friend. 

12. Hopes and Dreams

This is an inspiring and uplifting conversation topic that allows you to connect with a person on a deeper level. You can gain insight into what truly matters to him and what he envisions for his future. 

Asking about his dream job, the places he’d love to visit, or the type of life he hopes to create and sharing your own dreams and aspirations can encourage a sense of mutual trust and vulnerability as you both open up about your innermost desires.

[Also read: 10 Signs A Guy Feels Rejected By You]

13. Humor and Laughter

Injecting humor and laughter into your conversations can help to create a relaxed and enjoyable atmosphere. Share funny stories, jokes, or amusing anecdotes to lighten the mood and bring a smile to his face. 

Talk about your favorite comedians, humorous movies, or TV shows that never fail to make you laugh. Remember, laughter is a powerful tool for fostering connection, so don’t be afraid to embrace your sense of humor and explore the lighter side of life together.

14. Thought-Provoking Questions and Hypothetical Scenarios

Introducing thought-provoking questions or hypothetical scenarios can be a fun and engaging way to spark stimulating conversations. 

There are questions you can pose like, “If you could have any superpower, what would it be and why?” or “If you could travel back in time, where and when would you go?” 

Imaginative questions like these can help you know his thinking pattern and how creative he can be. 

[Related: How to Know If Someone Likes You Without Talking to Them]

15. Childhood Memories and Nostalgia

Revisiting childhood memories can be a delightful and engaging way to explore each other’s personal history and experiences. Walk through memory lane with him, talking about your favorite childhood activities, games, or family vacations. 

For instance, you might inquire about a specific childhood memory that made him laugh or left a lasting impression on him. 

This conversation topic allows both of you to reminisce about simpler times, and perhaps find common ground in shared experiences or similar backgrounds.

16. Sports and Fitness

Sports and fitness can be a lively and energetic conversation topic, especially if the guy you’re talking to is passionate about a particular sport or physical activity. Inquire about his favorite sports teams, athletes, or personal fitness goals. 

You could ask if he’s participated in any sports events or competitions, like marathons or charity sports events. By discussing sports and fitness, you’ll not only learn more about his interests but also gain insight into his dedication, discipline, and team spirit.

[Interesting: How To Attract A Man Physically In 10 Proven Ways]

17. The World of Technology and Innovation

With rapid advancements in technology and innovation, there’s always something new and fascinating to discuss in this realm. You could ask about his favorite gadgets, recent technological breakthroughs, or his thoughts on the impact of technology on society. 

Try to know about his opinion on self-driving cars, virtual reality, or artificial intelligence. 

18. Art and Creativity

Art and creativity can be a wonderful conversation topic to delve into the world of imagination and personal expression. Ask about his favorite artists, art styles, or creative pursuits. 

You could also discuss local galleries, art events, or exhibitions you’ve attended or would like to visit. Exploring art and creativity together can open up a world of shared appreciation, curiosity, and inspiration.

[Read: 8 Things That Cause a Man to Bond With a Woman]

19. Unusual or Unique Experiences

Sharing unusual or unique experiences can be a captivating way to learn more about each other and add a touch of excitement to your conversation. 

Asking about the most unexpected or surprising thing he’s ever done, like skydiving, swimming with dolphins, or attending a unique cultural event, and sharing your adventures with him can create a special bond between you two. 

By discussing these experiences, you’ll get a glimpse into his sense of adventure, openness to new experiences, and perhaps even his courage in the face of the unknown.

20. Discussing a Shared Literary Adventure

So, you’ve discovered that you’ve both read the same book – that’s awesome! This can be an excellent opportunity to exchange ideas and opinions about the story. 

You might chat about your favorite characters or scenes, and even debate certain plot twists or the author’s intentions. 

Let’s say you’ve both read “The Catcher in the Rye,” you could discuss your thoughts on Holden Caulfield as a character and the novel’s themes of innocence, loss, and growing up.

As you talk about the book, pay attention to how he interprets certain aspects of the story and the way he expresses his thoughts. Through this, you can get to understand his communication style, critical thinking abilities, and overall worldview. 

And don’t forget to share your own thoughts and opinions too – this is a conversation, after all. Engaging in a lively discussion about a shared literary adventure can strengthen your connection and enhance your understanding of one another. 

It’s an enjoyable and stimulating way to explore your mutual interests and spark thought-provoking conversations. Plus, it might even inspire you to read more books together and create your own ongoing, personal book club!


We’ve covered 20 interesting topics that you can use to strike up a conversation with a guy. We’ve also discussed a range of topics including hobbies, music, travel, food, and career aspirations. 

By using these topics, you can start a conversation with a guy that is both engaging and meaningful.

Understand that a conversation is a two-way street. Ask follow-up questions and share your own experiences. By doing this, you can build a deeper connection with the person and create a memorable experience.

So, go ahead and try out these conversation starters! You never know what interesting stories or perspectives you may uncover.


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Anita Oge

Meet Anita, a relationship writer with a passion for helping people navigate the complexities of love and dating. With a background in information science, she has a wealth of knowledge and insight to share. Her writing is sure to leave you feeling empowered and inspired.

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