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How to Keep a Conversation Going With a Guy: 7 Expert Proven Tips

So you finally connect with a cool guy, maybe for the first time in a bar or you’re on your first date from a dating app…and you are like a deer in headlights. You have no idea how to keep a conversation going with a guy…and as a result, you feel like you’re losing the chance to light a spark.

First off: you’re not alone. SO many women feel absolutely clueless when it comes to knowing how to keep a conversation going with a guy.

Some women talk 90-to-nothing because they’re nervous, barely letting him get a word in edgewise.

Some women are overly sarcastic, putting the man off.

Some women hide behind their intelligence, unsure of how to let a man see the real thing.

Some women are stone cold silent, sure they’ll say the wrong thing.

Whichever of these examples describes you, we’re going to work through some tips that will loosen you up and help you spark great conversation the next time you’re sitting across from a guy.

I guarantee that by the time you’re done watching the video above and reading the article below, you’ll be a more confident conversationalist.

Your Coach,

P.S. Want to take your conversation skills up even one more notch? Check out The Flirting Workshop. You’ll get tips on how to instantly grab the attention of any man in the room.


Whether you simply want to be a better conversationalist with any man or are specifically looking to engage a man you’re attracted to with witty banter, this article is for you. I know how intimidating it can be when you’re on a date or talking to a cute guy for the first time.

OMG, he seems so smart! I have no clue what to say!

How do I come off as flirty but not slutty?

He’s losing interest! If I don’t say something, he’s going to start talking to Sandra!

I’ve got lots of tips for you, so let’s get started.

How to Keep a Conversation Going With a Guy #1: Remember, Sometimes There’s No Conversational Chemistry

Just like you have a certain chemistry with some guys and not with others, the same goes for your conversational chemistry. It’s got nothing to do with your skills in this department; it’s just that you’re not compatible conversationally with certain guys (which probably means you’re not going to be compatible in other ways).

Back when I was single, I used to try to always improve my ability to talk to women, and I practiced every chance I got. But sometimes the conversations fell flat, and I felt like a failure. But then one day, a few years ago, I realized that there was sort of a formula to what was happening:

The conversations with 25% of the women I’d meet would be horribly awkward.

With 50%, the conversation would be meh. Okay, but nothing special.

And then 25% of the time, I’d click with a woman conversationally. It just flowed. I didn’t have to try to think of what to say. Naturally, these were the women I had the most success with dating! I stopped stressing about the 75% of the awkward to meh women and stopped thinking there’s something wrong with me, and just focused on finding that 25% of women who I had a lot of chemistry with.

You can do the same! If, when you’re talking to a gentleman, it’s like pulling teeth to get him to respond, or you just feel like you’re moving through tar trying to have a conversation, he’s not the one. Move on.

How to Keep a Conversation Going With a Guy #2: Key To a Good Conversation? Listen

Here’s something most people don’t get: most of a conversation is simply listening.

When I talk to women who are trying to figure out how to keep a conversation going with a guy, they’re focused on: what do I SAY?

I think a more important thing to focus on is the questions that you ask. Asking questions on a date is a great way to open up the dialogue. Veer away from questions that require only a yes or no answer. If you want to know how to keep a conversation going with a guy, ask these questions:

  • What are you passionate about?

  • What do you like most about your job?

  • What was growing up in your house like?

Questions are good, but just make sure you don’t come off like you’re trying to interview him for the role of husband (why did your last marriage end? how long have you been on dating apps? what are you looking for?).

How to Keep a Conversation Going With a Guy #3: Don’t Be Afraid of Silence

Realize that you don’t have to fill every silent moment with words on a date. When you’re nervous, that can be a challenge, especially if (outside of being around hot guys) you’re a talker.

Take time to sip your drink or chew your food (because: ladies don’t talk with their mouths full of food!). Give him a chance to respond to what you’ve said. Some guys need time to process things before they open their mouths, so don’t come off as an interrupter by constantly cutting in before he has a chance to say anything.

How to Keep a Conversation Going With a Guy #4: Repeat The Last Statement He Made

Here’s a really great tip on how to keep a conversation going with a guy when there’s a lull and you don’t know where to take it: just repeat the last statement he made.

If you struggle to keep a convo going, simply by saying the last phrase of what someone has said — especially if he’s a talkative person — will make him continue the conversation.

Him: So I was fishing on this lake, and all of a sudden, a fish flopped onto the boat.

You: A fish flopped onto the boat?

Him: Yea, it was a giant bass. 16 inches long. I grilled it when I got home. So good.

This is a dead easy way to keep him talking if you don’t know what to say yourself. It’s also a great way to validate his feelings and show that you’re truly listening.

How to Keep a Conversation Going With a Guy #5: Ask More Questions Based on His Answers

This is a great followup tip to the first one on how to keep a conversation going with a guy: when he answers one question, use his answer to ask another. Let’s go back to that fish in the boat example:

Him: Yea, it was a giant bass. 16 inches long. I grilled it when I got home. So good.

You: Oh, I suck at grilling, though I love grilled food. Do you like gas or charcoal?

Him: Definitely charcoal. It has a better taste.

You: Really? I never noticed. What’s your favorite thing to grill?

Him: Bacon-wrapped shrimp and grilled potatoes. Heaven. I’ll have to have you over sometime and make it.

Score. What he doesn’t realize is that you’re not doing much of the sharing in the conversation. Instead, you’re getting him to talk about himself. Science shows that talking about ourselves makes us really happy: in one study, researchers discovered that talking about yourself lights up the parts of the brain that respond to taking drugs, having sex, or just eating good food.

So you’re making him super happy to talk about things he’s into. Don’t you think the date will go well as a result?

How to Keep a Conversation Going With a Guy #6: Make Conversation a Fun Game

Sometimes a way to add a little fun to the conversation is to make it a little game. Ask him hypothetical questions like:

  • If you could live anywhere in the world, where would you live?

  • If you could only eat one thing for the rest of your life, what would it be?

  • What would your dream job be in your next life?

You could even tell him you want to play a game like 21 Questions or Would You Rather as a way to get to know one another.

These aren’t interrogation questions; they’re lighthearted ones with the aim of getting him (and you) to lighten up when you’re on a date. Come up with your own and make it a point to ask a few on your next date or interaction with a guy.

How to Keep a Conversation Going With a Guy #7: Compliment Him

Another way to put a man at ease (if he’s nervous) and maybe pave the way to good conversation is to simply compliment him. I feel like there’s more focus on men complimenting women (without going over the line in terms of what’s appropriate), and not enough on women complimenting men.

But we love to be complimented!

You can compliment him on his clothing, his choice of restaurant, his beer, his beard, his witty personality…whatever. I guarantee he will light up and keep the conversation going so you don’t have to worry about it.

What NOT to Do to Keep a Conversation Going with a Guy

We’ve put all our focus on what you should do to spark a man’s interest, but let’s cover a few topics that shouldn’t come up, especially if you’re on a first date or early texts with a man.

Don’t Talk About Your Ex

This should be a no-brainer, but you’d be surprised how many people — men and women — will talk about their exes on a date. They might just say something matter-of-fact about them (I was with my last girlfriend for 4 years.) or even get nasty and bitter (that f#$ing bitch took all my money and my favorite Counting Crows t-shirt!). Either way, it doesn’t leave a good impression for the person you’re on a date with.

Am I right?

Sure, after you’ve gotten to know each other, you can dive into one another’s romantic past, but not yet.

Don’t Talk About Money