How to keep a conversation going with a guy: 17 tips and 40+ examples!

The conversation is about to go extinct…what now?

Keeping a conversation going with a guy you like is a must if you want to grow closer to him because, as we all know, communication is essential.

It’s easy for conversations to die down, but you don’t have to sit there and watch it happen.

Do you want him yearning to talk to you? These 17 conversation tricks will kick your conversations’ quality up a notch:

1. Reply to his text messages on time.

Reply to his text messages in a timely manner

One of the biggest turn-offs I can think of is someone purposely delaying their responses all the time, simply because they want to elevate their “desirability”.

If you want this guy not to view your conversations as a chore, I recommend you reply to him on time, if possible—if you’re busy, it’s only fair you give him a heads-up beforehand.

I’m not saying you should drop everything to go running to him, though! Just that overdoing it will result in him possibly losing interest.

2. Make sure your replies aren’t short or boring.

On a related note, I’m sure he’d rather get no response, than a dry response; make sure that you don’t give him one-word or boring replies as they might contribute to your conversation going downhill.

“K.”, “Cool.”, “I’m good.”, etc.—texts that have and require no further elaboration will leave a bad impression and make him less willing to text as a result.

3. Let him speak.

Most people enjoy being the one doing most of the talking, but did you know that’s detrimental to a two-way conversation?

Make sure your conversation is balanced in terms of who’s speaking and who’s listening; let him share his stories, express his feelings, and speak his mind.

This way you’re not the only one getting attached to the conversation.

4. Ask him questions about the story he’s telling.

Ask follow-up questions about the story he’s telling to show him you’re interested and not simply waiting for your turn to speak.

Let’s say he’s telling you about how he went out with his friends last night, to which you’re going to ask questions such as:

“Where did you go?” or “Did you have fun?”.

5. Chime in with your opinion as well.

You don’t want him to be the only one speaking—remember that the conversation needs to be balanced.

Whenever he talks to you about something, see to it that he knows you’re an interesting person with a lot to say.

So, don’t be shy to convey your opinions, and feelings to keep the wheels of the conversation going!

6. Talk about a similar experience from your past.

Bringing up similar experiences that are relevant to one of his stories will help the two of you relate to each other, and people LOVE talking to people they relate with.

If, for instance, he’s telling you about how one of his pets ran away when he was little, talk about one of your pets running away as well after he’s done with his story.

7. Be supportive, understanding, and empathic.

Everybody deserves to feel heard, especially when talking to someone they deem close.

When a guy is opening up to you (which they rarely do), you must show them it’s okay by being supportive and understanding.

Take their side if needed, just don’t make them feel bad about it or as if you can’t wait to jump to the next topic!

8. Show him you’re interested in your conversation too.

To keep him interested, you must let him know you’re interested as well:

Don’t leave him hanging;
Ask relevant questions;
Comment now and then about how interested you are;
Don’t rush him into wrapping his topic up.

Sometimes people let the conversation burn out when they feel as if the other person isn’t tuned in.

9. Don’t just ask yes or no questions—go a bit deeper.

Asking open-ended questions ensures you and your guy have more interesting conversations that make him inclined to keep talking to you.

Ask questions such as “What’s the best memory from your childhood?” instead of “Do you have good memories from your childhood?”.

The right topic ought to have him keep talking and loving every second of it.

10. Talk about something you both like!

Want to have him addicted to your conversation? Show him that you two have a lot in common by talking about specific things you both like.

Do you like the same music? What about movies? Better yet, sports (something the both of you can physically meet up to do).

Common ground makes for excellent conversations, especially when talking to your crush.

11. Get to know him better.

Guys will return the energy once you express the desire to get to know them better.

Learn about his hobbies;
Delve a little bit deeper into his personality;
Ask about his career goals or what he’s currently doing;
Get to know the favorite people in his life.

The more curious and keen you appear, the more flattered he’ll feel, making him feel giddy every time you two talk as a result.

12. When the time calls for it, compliment him.

You don’t have to go overboard or anything like that—occasionally complimenting him while talking will, however, help you with your predicament.

Let’s say he’s talking to you about how he got the highest grade on a test in his class; he’d most likely appreciate a pat on the back for his hard work.

“Good job! You’re an intelligent, hardworking guy and I never doubted you for a second.”

13. Have a playful, easygoing attitude.

If it hasn’t been a long time since you two met, it’s always recommended to be lighthearted in the beginning (don’t worry, things will get serious with time).

This means no pressuring him into responding to your texts and no starting serious, personal topics out of nowhere!

Once he knows he can trust you, he’ll open up by himself—until then, keep playfully teasing each other and talking about fun things.

14. Is the subject dead? Don’t be scared to change it.

While conversing, two people must avoid letting the conversation die at all costs.

Switch to an interesting topic if your conversation is nearing its end—your guy could be too shy to do it himself for all you know.

“On a completely unrelated note, did you know that…”

15. Is he the spicy type? Talk about something controversial!

Every contentious person loves getting their simulation fix for the day. Is your guy the argumentative type?

If he is, then make things more fun for him and you by talking about something controversial (e.g. a viral topic people are divided on).

If you disagree with his view, respectfully explain your point of view; many people are attracted to authentic, confident people.

16. Find something eye-catching about him.

Is he wearing something cool? Don’t hesitate to point it out as not only will it make him feel good, but it will also keep the conversation from shutting down.

Grasping at random things will allow you to switch topics as well, e.g. “I love that hoodie! Have I ever told you how much of a fashionista I am?”

17. Transfer your conversation offline or online, depending.

Variety in communication has got to be one of the most useful things in keeping a conversation going with a guy.

Just because you might’ve met him online or offline doesn’t mean you can only communicate with him online/offline respectively.

Let me take an example: if you’re only able to talk with this guy between classes, you can try texting him for a change.

“Hey, it’s me! What were you about to say before the bell so rudely interrupted us, LOL?”

The right questions: What you can ask a boy to keep the conversation going (and fun).

Questions are a life-saver when it comes to keeping a conversation going with a man as they make way for more conversation.

You can catch your guy’s attention by asking questions about:

His life in general;
His hobbies and interests;
His childhood;
His professional life, etc.

Below you can find 42 examples of fun and cute questions that will catch his attention and make him want to keep the conversation going.

1. “What’s the thing you’re most proud of?”
2. “Who is your favorite person in the world?”
3. “What do you like doing in your free time and why? Give me the deets!”
4. “What song/singer has had the biggest impact on you?”
5. “Who’s someone you look up to? Any specific reason why?”
6. “Are you currently working towards any goals?”
7. “Have you ever had any pets? What’s your favorite animal?”
8. “I love traveling! What is the most mesmerizing place you’ve been to?”
9. “What’s something silly you believed as a kid? Mine is…”
10. “What’s your favorite food? Oh! What about your favorite restaurant? I’m looking for new places to try.”
11. “What was your favorite TV show as a kid? OMG, do you remember [certain show]?”
12. “What do you do in your free time? Any hobbies you’d like to talk about?”
13. “What’s your favorite feature about yourself?”
14. “Here’s something spicy: do you have any pet peeves? I sure do.”
15. “Are there any bad habits you’d like to let go of?”
16. “Is there anything you can’t live without?”
17. “I have a fun question! What is the most attractive thing in a person, in your opinion?”
18. “What’s the most frustrating thing about working in your profession?”
19. “Do you have anyone who just gets on your nerves?”
20. “Is there any risk you’re glad you’ve taken?”
21. “What did you think you’d be growing up?”
22. “What’s your favorite type of music? Any song you listen to every single day?”
23. “What’s your favorite game right now? PC, console, or mobile!”
24. “When is the last time you said ‘Screw it!’ and took a risk?”
25. “Do you listen to any podcasts? They’re all the rage now. What’s your favorite one?”
26. “Spicy vs. sweet food: which one needs to go?”
27. “Favorite article of clothing? Tell me all about it!”
28. “Did you know I had [certain phobia]? Do you have any irrational fears?”
29. “Where do you usually play games? I’m a console player all the way!”
30. “Which do you prefer and why—pizza or burgers?”
31. “Favorite dessert? I’m an apple pie connoisseur myself.”
32. “What is your favorite holiday? If you’re a festive person, that is!”
33. “Do you have any favorite scents you can’t go one day without wearing?”
34. What’s your opinion on the advancement of technology? Do you think it poses a threat to humans?”
35. “What’s something you’d like to learn? I’ve always wanted to learn how to play the piano.”
36. “What is your favorite movie?”
37. “Do you go to concerts often? If so, in which one did you have the best time?”
38. “What’s the best activity to do with friends? Me and my friends are looking for something fun to do.
39. “Have you ever read a book so interesting you had to stop mid-way and catch your breath? Which one was it?”
40. “You know [friend in common] too? Where did you meet?”
41. “In your opinion, what’s the best TV show? An absolute classic.”
42. “Which is your most controversial opinion? Come on, I won’t judge…”

Don’t sweat it, keeping a conversation going is a breeze!

Now that you know all the secrets to keeping a man interested in your conversation, doing it will be a breeze.

Be yourself, have fun, and don’t be shy to express your thoughts and feelings—he will love each second spent talking to you.

But, of course, first, make sure you’re not the only one interested in talking!

Love,

Callisto.