What to Talk About With a Guy: 18 Things That Keep Him Interested

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So it’s been a while since you had to figure out what to talk about with a guy.

Maybe until recently, you were married and your discussions in your relationship centered around finances and the fact that he never took the garbage out. But now you’re dating again, and you’re like a deer in headlights on a first date.

You need witty banter! Intellectually-stimulating conversation!


Not to worry, ladies. This is kind of my area of expertise. You see, before I started coaching women on how to find amazing love, I coached men to help them find the courage to walk up to Sexy Confident women like you and start talking. So I gave them all kinds of proven tips on how to talk to women. Now I’ll just reverse this advice to help you figure out what to talk about with a guy!

Notes for What to Talk About With a Guy Via Text

Before I start giving you ideas on what to talk about with a guy in person, I want to point something out: texting is a different game from phone or even in-person conversations. I’ve written several articles with tips on texts you can send a guy you like, but let me give a few tips here.

1. Keep Them Short and Funny

Texting isn’t email. It isn’t a conversation. It’s designed to be short and functional. Yes, we’ve all been guilty of having actual conversations via text, but man, don’t your fingers get tired? If you start to get into a conversation that warrants more dialogue, suggest a phone call.

2.  Ask Questions, but Also Let Him Do Some Asking

It’s also easy to fall into the trap of the one-sided questions. You ask a question and he answers. You ask another…and he answers. Before long, you’re feeling like the leader of the Spanish Inquisition! Pull back before you freak him out.

If he doesn’t ask you questions naturally, say something like, “Whew! I’m asking a lot of questions. Your turn!”

Here’s What to Say to a Guy You Want to Ask You Out


I’m going to go through several different scenarios where you might need to figure out what to talk about with a guy. Each one is unique in that you either don’t know him at all, you know him a little, or you know him slightly more. It will get easier to know what to talk about with a guy the more you know him.

So let’s start at the beginning. You are interested in a guy, whether you spotted him across the bar or maybe have known him from your friend group for a while. You want to transition from either being strangers or being friends into being something more.

3. Ask Him His Name

Obviously, this is a tip for a guy you don’t know at all. Sometimes you’re stumped for what to say because you want to come off as super cool, but in reality, simply starting with an easy question like “what’s your name?” can get the ball rolling.

From there you can comment on his name if it’s unique (“Duffy? That’s an interesting name! What’s its origin?”), tell a funny story about someone with the same name (not an ex!), or just tell him your name.

4. Ask if the Drink He’s Got is Good

Men are pleasantly surprised when women walk up to them and start talking, so just know that you cannot fail, no matter what your opening line! If you’re at a bar and he’s sipping on something, ask what it is. Pretend to be considering ordering one yourself and want his input on it.

If you’re bold (and you should be), ask to try it. If he’s willing to let you drink from his glass, he’s definitely not going to let you walk away!

5. Find Out if He’s Single

This can be a tricky topic to approach, but it’s better to find out up front that he’s taken and not waste your time further!

If you’re talking to someone you met at a bar or party, you could ask, “are you here with your girlfriend?”

You could also listen for clues in conversation. If he mentions going on vacation, you could ask if he went with his family or partner. That’s his opportunity to say, “nope, I’m single!”

You could also mention a dating app and see if he picks up that thread. If he’s single, he’ll either also be on dating apps or have a strong opinion about them.

6. Tell Him About a Cool Event You Want to Go To (Hint! Hint!)

If the guy you’re interested in is one you already know, you want to see if he’s interested in spending some one-on-one time with you away from your circle of friends. If you know he’s really into whiskey (and so are you), bring up a cool whiskey-tasting event happening next weekend and see what he says.

If he says, “that sounds cool!” then put on your confident hat and ask him to go with you. Just make it clear that it will just be the two of you before he invites the rest of the crew!

7. Ask if He has Plans for the Weekend

He has no plans…

You have no plans…

Why not make some plans together? If he’s interested, he’ll make a point of mentioning some free time he has. Maybe he tells you he’s going out with his boys Friday, but will be puttering around the house on Saturday. There’s no point in him mentioning this unless he wants to let you know he’s available. Tell him you don’t have anything planned either (except that whiskey-tasting thing) and see if you can make plans together.

What to Talk About With a Guy on a First Date

first date

Cat got your tongue on a first date?

Okay, so you made it this far and are actually on a first date (possibly the first one in a very long time). Don’t panic about keeping the conversation flowing! Here are a few pointers for what to talk about with a guy on a first date.

8. Ask Questions About His Interests

Don’t you love it when men ask you what you’re into? Talking about your (and his) interests on a first date is a great way to break the ice. It also helps you predict whether you will be compatible: in a study on marriage by The PEW Research Center, 64% of married couples said that having shared interests is key to a successful relationship.

Whether you have shared interests or not, asking what makes him happy and what he does in his spare time is a great conversation-starter.

9. Share Funny Stories from Your Childhood

Here’s another tip for what to talk about with a guy that doesn’t involve you peppering him with questions. Share a hilarious story from your childhood. Maybe you’re at a restaurant, and on the menu is a drink with fresh pressed apple cider. It reminds you of the time you climbed the apple tree at your grandparents’ house and fell out and broke your ankle! Share the story and have a good laugh. He’ll likely respond with his own childhood story.

10. Play the “Would You Rather” Game

Here’s another fun one based on a kids’ game called “Would You Rather:” the idea is that you ask your date which of two choices he’d rather do. Here’s an example:

Would you rather lose your sense of smell…or your sense of taste?

The questions can be silly and nonsensical, or you can use them to get to know him a bit better:

Would you rather never fall in love in your life…or have your heart broken over and over?

Take turns and see what comes up!

11. Find Out About His Dreams

While “what do you do” always comes up as a question on a date, it doesn’t always accurately explain who a man is. If he crunches numbers for a living and just does it to pay the bills, you don’t get a real sense of what drives him, what he’s passionate about.

Instead, ask what his dreams are. What did he always want to do as a kid? What would he do if money were no object?

This kind of free-form conversation can really open him up and let you get to know him faster.

12. Inquire About His Job

Okay, I’m not completely taking the whole job thing off of the list of what to talk about with a guy, because obviously work plays a large role in all of our lives. But once you get past finding out what his job title is, ask more questions:

  • What does a typical day look like?
  • What do you like best about what you do?
  • What do you like least?
  • Do you like the people you work with?

Even if he detests his job, he will likely perk up and find some good points to share.

13. Talk About Music or Movies

Another softball subject is popular culture. What types of movies or music does he like? And while you don’t have to be aligned exactly in the types you like, you might be dismayed to hear he’s really passionate about heavy metal music. Better to know now than later!

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This conversation can, if you’re lucky, lead to the two of you deciding to go to a movie or concert if your interests are aligned!

14. Talk About Food

Another subject everyone loves talking about: food! Find out what types of cuisines he likes. What he would never ever try (bugs?). The most adventurous thing he’s ever eaten. Then share your stories. Maybe even dare each other to get out of your comfort zones by planning an ethnic meal for the next date!

How to Keep the Conversation Going as You Date

older couple

It takes effort to keep the spark alive.

The longer you date a man, the more the conversation changes. Once you become a full-fledged couple, it becomes easy for things to stay centered around mundane topics (laundry, what’s for dinner). You have to make an effort to engage in intellectual conversation to keep that spark going.

15. Talk About Something You Read or Saw on the News

What better topic to talk about than a trending news issue? Whether it’s the study you read about on orangutans or the current political climate (Trump is always good for a robust dialogue, no matter how you feel about him), find something that will engage you and your love in meaningful conversation.

16. Read the Same Book and Discuss it

Here’s a fun activity you can do together: take turns picking a book and having your own two-person book club. When you’re done, discuss it over dinner and drinks. Feel free to pick books you don’t think your boyfriend would have picked just so you can have a little opposing dialogue.

17. Explore Your Memories Together

The longer your relationship, the more memories you’ve made. Look back at shared adventures and reminisce together about it.

“This time last year, we were in Sardinia together!”

You can look back on the early days of dating, trips you’ve taken together, even stressful things you overcame together.

18. Talk About What You Want in Your Future Together

Just like the longer together, the more memories you have in your past, the longer you’re together, the more you’ve got to look forward to in your future. What does your future together look like? You can make real and fantasy plans. Maybe you talk about what you want to do when you retire (sail the seven seas) or what you’d do if you won $5 million in the lottery.

The point here is: it doesn’t matter what you talk about…as long as you keep talking to build a solid communication foundation in your relationship!


No matter what stage you’re in with a guy — from meeting him for the first time to a first date or even years down the road — it can take effort to know what to talk about with a guy. Above all, be genuine. Don’t talk about things just to impress him, particularly if they’re things you don’t really know anything about. Talking about what you do know about and have an interest in is a better strategy to get his attention!

What do you think? Share your thoughts below...

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4 years ago

Have never been in relationship and the is this man I knew from a friend we have never met .he’s interested in me but I have nothing to talk about with him, what should I do or what should we talk about ?

3 years ago
Reply to  Suwana Bowa

I thin the post kind of already answered your question no?

3 years ago
Reply to  Suwana Bowa

talk about yourself and dont forget to ask questions about him aswell !!!

3 years ago

So cute! I love questions to help you get to know each other better.

2 years ago

What should I do since We are in quarantine and we have to stay 6 feet apart of each other part of each other not a pool to the guy like wood what should I do about that 13-year-old 14-yearOld who is asking for advice

2 years ago
Reply to  Emily libeck

Try video chatting him a lot to keep the communication going.

2 years ago

So I I’m dating this guy, but it happened really fast I don’t know practically anything about him. Stupid right? I know. I really like him and he really likes me. We sort of have the same interests, though.
We’re losing the spark and I need to keep it alive. It seemed easier when we were just casual friends trying to get to know each other better. I need help.
Who can relate?

2 years ago
Reply to  Fortune. O

Try asking him… Can I ask you a personal question? If I were to give you a magic wand and you could use it to make your life anything you want it to be, what would it be like?

2 years ago

I get all the tips, I really do. But I just don’t know how to talk to him. Sometimes he’s sooo unenthusiastic, I’m drained and bored. Or it could be that he goes deep and personal in the conversation that I am just lost and slightly afraid.

2 years ago

it did not help i am 15 and i am talking to a guy and we don’t talk about anything and i want to but i don’t know what to ask

2 years ago
Reply to  CJ

I am 13 but I am in the same problem as you

1 year ago

I don’t know if I am in a situationship but I feel like. So this guy and I love ourselves so deep but I am not willing to date him and his asking if we can be hugging and holding me around the waist kissing. Its not relating to this post but I need advice !!

1 year ago

does anybody know what to do when you dont know what to say to the guy you are dating and you dont really talk much please help

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