50 Interesting Things to Talk About with a Guy

What are good topics to discuss with a guy you like?

How do you keep a conversation going with a boy and steer the interaction in the direction you want? And what are good topics to talk about are not only fun but also build rapport with him?

These are all great questions. Here’s the good news: Talking with new boys is easy when you know what topics to discuss and what to avoid.

And when you also follow some “best practices” in general conversation, things become even more rewarding.

You’ll learn 50 things to discuss with a guy in this article. They’ll range from friendly and harmless to daring and sexual, but all of them are guaranteed to keep a conversation going with him.

Find the ones you can easily talk about, then go out there and make new friends.

50 Random Things to Talk About With a Guy

So, what are good topics to talk about with a guy? Here are 50 of them.

The first few will be conversation starters, followed by small talk topics.

Later, you’ll come across topics that deepen the conversation, which is great for building rapport. And lastly, we have some topics to save for the men you’re interested in.

Let’s dive right in, starting with:

#1: His Name

This one’s the most obvious. Any conversation becomes ten times easier to carry when you know each other’s names.


A simple: “Hi, what’s your name?” is enough to start a conversation with a new guy, no matter who he might be.

It’s even better if you can introduce yourself at the same time. For example, you can say: “Hi, I’m __, what’s your name?” or, “Hi, what’s your name? I’m __.”

You build extra trust by offering your name first, which makes him open up more with you.

It’s also an opportunity to compliment him if he has a nice name. “Nice name. I’ve always liked __.” It’s a good way to break the ice with a new guy.

#2: Animals and Pets

As you talk with him, you can talk about animals and pets.

You can say: “Hey, I just need to know: Do you like dogs? Because if you do, I think we’ll get along well.” It’s hit-and-miss, but if you love dogs and he does, you’ve instantly made a new friend.

A variation of this is simply asking: “Do you have any pets?” and let him tell you if he does. If he doesn’t, that’s fine—choose one of the other topics in this list of 50.

#3: Travel Spots: Good and Bad

Do you notice something touristy about him? Perhaps he’s wearing outdoor gear, or a theme park shirt, or a bracelet whose design you recognize. “That looks interesting,” you say. “Do you like to travel?”

Such a simple question can immediately segue into a conversation about travel.

You can ask him about the best places in the world he’s been to and the worst ones. (The bad experiences tend to make for pretty good conversations!)

You can also share your experiences and see if you’ve visited the same locations.

This is especially useful if you like traveling yourself. Figuring out your compatibility early on is going to help develop your relationship. I would also recommend contacting a professional who can analyze your situation and help you figure out the exact approach you can take.

#4: Your Favorite Movies and TV Shows

Do you like movies and TV shows? Do you follow certain shows and actors? If so, this is a great option to kick off a conversation with a guy.

Movies and TV shows make for good small talk fodder.

You can ask him something specific, like: “Did you like how they ended Game of Thrones? I have mixed feelings about it,”

or something more general: “What shows are you watching on Netflix these days? I need recommendations.”

#5: Music You Both Like


You can also explore his tastes in music. Ask him: “What kind of music do you like?”

He might give you a list of genres that he enjoys. And then he’ll ask if you’re interested in those genres, as well—and it’s a bonus if you do.

If you don’t, then you can still ask him to tell you what he likes about it.

Be open to the possibility of developing a liking for it. You can even ask him to send you a mix for you to listen to later in the evening.

And if you want to spice up your next conversation with him, try to pick a few songs from his mix that you like, and gush about it at your next meeting.

#6: Sports

If he’s wearing a sports shirt, a baseball cap with a team’s logo on it, or a college football jacket, that’s an instant conversation topic for you. You can say: “Hey, nice hat. You a fan of the Niners too?”

Such a simple question, but it can lead to a conversation around players new and old, big sporting events of the past, controversies on and off the field, court, or racetrack—the possibilities are endless.

You can use a sports term when the topic has run its course, and it’s time to switch gears.

For example, “Let’s take a time out from sports and talk about ___ instead,” or “Okay, that’s offsides—let’s switch gears a bit.”

#7: Food: Good and Bad

Everybody loves food, so it’s a good topic to break the ice. “What’s your favorite cuisine?”, “What’s your comfort food?” and “Can you cook?” are fun ways to start conversations.

If you want to spice things up (heh), you can ask him something contentious like: “What food do you hate?” or “Does pineapple belong on pizza?” and see where it goes.

It may lead to some interesting revelations—not just about the food he likes and dislikes, but also about his personality and background.

#8: Ask Him About His Hobbies, Interests, and Passions

“So, what do you do for fun?” This has always been a great conversation starter, and for a simple reason: People like to talk about themselves and the things they love.

Men love talking about their hobbies, interests, and passions.

Ask him the question and let him reveal a bit about himself. If his hobbies interest you, ask him to tell you more.

And if you’re feeling particularly bold, you can tell him: “That sounds really fun. You should take me to see it sometime.”

As a bonus, many couples start out over shared interests. If you’re attracted to him in a more-than-friends way and share the same interests, you’ve found a good catch.

#9: Tell Him About Your Hobbies and Passions

Speaking of hobbies, you can tell him about yours in a pinch. Let’s say you’re into making digital art. You can ask him: “Have you ever done digital art? Because I do it all the time. It’s a hobby that pays.”

You can then show him examples of your work and explain a bit of history about each one. It’s a good way to gauge his willingness to interact with you.

If he shows genuine interest, that’s great. If he’s at least polite, that’s still good.

If he says something dismissive like “That’s boring,” take it as a sign that the conversation isn’t going anywhere. Thank him for his time and end it.

#10: In a Bar or Party? Ask About His Drink


This one’s a good conversation starter with men when you’re at a bar or party, where everyone’s likely to be holding a drink. You can ask him: “I’ve never seen that cocktail before. What is it? Is it good?”

If you’re both in a party mood, he might buy you the same drink or give you a sip. It’s a great way to break the ice, and alcohol always greases the wheels for a more enjoyable interaction.

#11: Your Careers

This is another one of the “default” topics or the ones that always seem to come up in a first conversation. “So, what’s your profession?” or “Which company are you connected with?”

His answer will clue you in not only on what he does but what he’s like, as well.

Of course, be ready to be asked the same question. But, on the other hand, if your career is something you’d rather not talk about, you might want to skip this topic entirely.

#12: Compliment His Fashion Sense

Do you like something he’s wearing? Then tell him about it. It can be simple: “Hey, I like your shirt,” or “That’s a nice hat.”

After he thanks you for the compliment, you can ask him where he got it, and he might regale you with a story.

Other times, he might return the compliment. He’ll say something like: “Thanks, I like your sweater,” and that’s it. That’s not a problem—just segue into one of the other topics on this list.

It’s important not just to keep segueing from compliment to compliment, though. To keep the conversation engaging, you guys can’t just go back and forth, complimenting each other.

Also, a guy will take a compliment about fashion more seriously from a woman who is fashionable herself.

#13: Books You’ve Read

After 3-5 minutes of small talk, the conversation feels awkward. That’s your cue to deepen the conversation and build some real rapport.

How do you do that? This is a good option—books you’ve both read.

You can ask him: “So, are you a reader?” or be more direct and ask: “Have you read Neil Gaiman’s work?”

Like most of the topics on this list, asking about the books he’s read is an attempt to find some common ground. If you’re a reader and he is, too, then you’ve made yourself a new friend.

#14: Your Ideal Pets

This is a good way to deepen a conversation, but be careful as it can get controversial.

For example, you can say something like, “I’ve always wanted to own a tiger,” or “I’ve always wondered what it’s like to take care of a ferret,” and see how he reacts.

Most guys will ask you why or give you some insight if they’ve had experience caring for the animal you mentioned. Others will tell you the animal they’ve always wanted to have.

This topic is controversial because some people take animal rights very seriously and will take offense to your suggestion of owning exotic pets.

So broach the topic gently, and switch to a different topic when you sense some indignance.

#15: Social Media

This one’s easy. Ask him: “Are you on social media?” or, more directly: “Are you on Instagram?” and he’ll flip out his phone and show you his profile and photos.

A guy’s social media stories are treasure troves for conversation topics. If, say, you spot a photo of him skydiving, you can ask him: “When was this? What was it like?”

Naturally, when you’re on the same social media platform, you’ll add each other in minutes, opening up more opportunities for conversations in the future.

#16: The Weather

No, don’t just comment on how nice or how bad the weather is. Instead, go deeper with questions like:

  • “Looks like it’ll be heavy snow this weekend. What do you like doing when you’re snowed in?”
  • “You mentioned you’re from Kentucky. What’s the weather like there this time of year?”

Such a conversation can segue into fun things to do when the weather is cold, hot, wet, etc. One mention of “I’ve always wanted to try that,” and you’ll have planted the seeds for a future date.

#17: Jokes You Recently Heard


If your interaction with a guy reminds you of a joke you recently heard, wait for a break in the conversation, then share it with him.

You can say: “Speaking of, that reminds me of a joke I once heard…” and proceed to tell it.

Sharing jokes you recently heard is a good way to test his sense of humor.

He may be easygoing and laugh with you, even if your joke is controversial or dark. Meanwhile, if he gets offended by it, then it’s probably a sign he won’t be a good friend to you.

#18: Funny Stories From Your Past

Likewise, if your conversation with him reminds you of funny or profound stories from your past, share them with him during a lull. “That reminds me of something that happened the first time I went to this town…”

If he’s interested in you, he’ll ask follow-up questions about your story or share a similar one. It’s another good way to gauge whether he likes you or if he’s just being polite.

#19: Faith, Religion, and Spirituality

You can ask him: “Do you have a religion?” or “Do you practice spirituality?” and see how he takes the question.

As controversial as it might be, this is an important topic to broach when you’re looking for a long-term partner.

Your spiritual views as a couple are critical to your relationship’s longevity.

When you meet a guy you really like, you might want to cover this base before taking things to the next level with him.

#20: The Last Thing That Surprised Him

This is a good question to pop during a lull in your conversation. You can say: “Okay, let’s shift gears a bit. What was the last thing that surprised you?” and see how he reacts.

When you sense an awkward silence coming up, pop this question and see what happens.

He’ll answer your question if he’s socially savvy enough to keep the conversation going.

Meanwhile, if he refuses or says something like: “What kind of question is that?” he’s probably not the type you want to get too invested in.

#21: What He’s Most Proud Of

When he’s talking about his past, especially about his achievements, this is a good direction to steer. Ask him: “What are you most proud of?” and see what he values most about his history.

Was it an achievement? Then he must be a goal-oriented guy.

Was it an act of charity he made? He must have a heart of gold. 

Or perhaps it was a word of encouragement he received from someone he looked up to. In that case, he relishes the sense of victory and validation.

You’ll be surprised at what you’ll learn when you ask a guy what he’s most proud of.

#22: Funny Conversations

Is your conversation with him reminding you of funny convos you’ve had with others?

By all means—share it with him. You can say: “What you just said suddenly reminded me of something my first boyfriend told me…”

As long as the story you’re telling is relevant to the discussion, you’re welcome to share it. He might also regale you with a tale or two from his own experiences.

#23: Your Biggest Ambition

As your conversation with him deepens, the topic of your biggest ambitions and dreams will likely come out. And this is when you can let your hair down a bit and let him know your biggest ambition in life.

Let’s say you’ve always wanted to be an astronaut. Tell him: “Call me crazy, but I’ve always wanted to be an astronaut,” and then tell him how you got that ambition in the first place.

It doesn’t matter what your ambition is. But, if it’s important to you, share it with him. How he responds to it will reveal more about the “real him.”

#24: Your Plans for Your Life

Of course, the ambitions you share with him can be more realistic.

You can tell him about your plans in life—concrete, measurable, and with deadlines.

You can wait for him to ask you something like: “So, what do you plan to do in the future?” before telling him if you don’t want to accidentally overshare.

#25: Your Daily Routines


You can also ask him: “You seem to be into a lot of interesting stuff.

What’s your typical day like?” and see what he tells you. It’s a great way to know him better.

In addition, it’s a sneaky way to know his schedule—that way, if you like him, you can set up a second date much more easily.

Don’t forget to return the favor and let him in on your daily routine. If he has the initiative and is interested in you, too, he might schedule the next date all by himself.

#26: Your Greatest Fears

It’s not unusual for a deep conversation to broach the darker side of your lives.

One of the more common topics in this realm happens to be your respective greatest fears. So you can ask each other: “What are you most afraid of?”

When this happens, be on your guard. His greatest fears can reveal his worst traits: Anger, bitterness, and maybe even evil. So you’d be smart to limit your involvement with him from then on.

#27: His Long-Term Goals and Dreams

You can ask him about his long-term goals and dreams on the brighter side of things.

You can ask him: “What do you plan to do with your life?” And see just how lofty his goals are. Allow him to impress you even just a bit.

Asking him this question will help you see whether he’s got big plans for the future, if he’s a loafer, or if he’s an in-between Average Joe. Which type you like best is up to you, of course.

#28: Shared Interests

As your conversation goes along, you’ll inevitably stumble upon shared interests and things you have in common.

One of you says something they like, and the other says: “Hey, me too!” You’ve gained a few extra minutes of conversation.

When you find interests you share with him, get into details. Ask questions, tell stories, and share insider secrets.

You might even consider scheduling a future date around that said interest—that’s going to be hard to say “no” to.

#29: Current Events

Another fun topic to talk about is current events, whether local, national, or global. That said, it’s best if you discuss the news that’s positive, funny, or controversial in a humorous way.

That means you might want to avoid divisive topics like partisan politics, at least until you’ve established he’s not one to be easily offended or irritated.

#30: What He’s Obsessed About at This Moment


Here’s another good segue topic you can use. Before switching topics, tell him: “Let’s shift gears a bit. Here’s a quick question: What are you obsessed about now?”

He might take a moment to think about it, but he’ll tell you what’s on his mind if he likes you.

When using this tactic, be ready for two other outcomes. First, he’ll likely ask you the same question—so be prepared with a good answer.

Second, he might decline to answer or just say, “I don’t know,” in which case you simply move on to a different topic.

#31: What His Favorite Thing in His Life Is

Here’s another thought-provoker: “What’s your favorite thing in life?” Go ahead and pop this question and watch him try to decide among the things he loves.

He might answer with a kind of food, an event, a hobby, or something deeper—like a value or a cause he’s fighting for.

Likewise, think about it for a moment. What’s your favorite thing in life?

What would it be if you had to choose just one thing to label as your favorite? It’s a good idea to have an answer if he asks you the same question.

#32: Your Favorite Memory

If you asked him: “What’s your favorite memory?” you’ve essentially added at least one more story to your conversation with him.

You could keep the conversation going by being more specific: a childhood memory, his favorite experience in high school, etc.

Nostalgia is always good conversation fodder, but as you might expect, a topic like this is best reserved for a deeper conversation.

If you’ve known each other for a while, he won’t mind answering the question, but he might object to revealing something personal to someone he just met.

#33: What He Thinks is His Greatest Weakness

This one’s a twist on the “what’s your greatest fear” question. Instead, you can ask him: “What do you think is your greatest weakness?”

The question forces him to be honest and vulnerable with you, which may not be something he’s willing to do unless you’ve already built some rapport.

Personal questions, including this one, can be intrusive, so use them sparingly.

#34: Work You’d Love to Do For the Rest of Your Lives

Ah, the classic conversation starter. “If money weren’t an object, what would you do with the rest of your life?”

It’s always fun to think about, and it permits him to touch base with his deepest desires and share them with you.

The deeper the conversation and the friendship you have with him, the more revealing and profound his answers will be.

And, as always, have your own answer ready. What would you love to do if money weren’t an issue for the rest of your life?

#35: Your Plans for the Weekend

This one’s a simpler question, and it’s appropriate to ask when you’re enjoying the conversation so far. Ask him: “So, what are your plans for the weekend?” And if he has made any plans, he’ll tell you—and you can see if you can squeeze yourself into his schedule.

Asking for his weekend plans allows you to hang out with him again—ask: “Oh, that sounds interesting. Mind if I tagged along?”

What if his plans don’t seem fun or interesting enough for you? Move on to the next conversation topic and see if that yields a dating opportunity.

#36: When to Meet Up Again

Sometimes, your conversation with a guy ends up being so good that you must meet up again sometime, no matter what.

Guess what? That’s another topic you can talk to him about. You can tell him: “This is great. We should totally hang out again sometime soon. What do you think?”

If he’s having a good time, too, then he’ll inevitably say “yes.” And if he has initiative, he’ll suggest the date, time, and place as well—and if you’re interested in him in a more-than-friends way, his initiative is a wonderful sign.

On the other hand, he might not feel the same way if he’s unsure or noncommittal. But, again, it shouldn’t bother you—simply switch to the next topic with the intent to end the conversation soon.

#37: An Event You’d Like to See

Is there an event coming up that you’ve been dying to see? Tell him about it: “My favorite band is coming to town, and I’ve always wanted to see them in concert.” Then see if he feels the same way about the event.

If he does, then that’s yet another opportunity to set up a date in the future.

#38: Current Relationship Status


Now, what if you really like him? What if you’re feeling some romantic or sexual tension between you?

Obviously, you don’t want to waste the opportunity to see if he’s really lover-material. And so, you must know how to steer the conversation toward more romantic grounds.

The easiest way is to ask him about his relationship status. For example, you can ask: “Are you single?” or, less directly, “You sure your girlfriend won’t mind you talking to me like this?”

His response to your question will likely tell you how he feels about you.

#39: Activities You Both Haven’t Tried Yet

This is another fun question to ask a guy: “Have you ever wanted to try something in your life, but you’ve never had the chance even until now?”

If he asks for specifics, you can egg him on by suggesting visiting a country in the world or trying a hobby that’s always intrigued him, and so on.

You can tell him about an activity or two that you’ve wanted to try but never have. Then see if it uncovers a shared interest between you.

#40: Future Activities

This topic “seeds” the interaction for future dates. “So, what do you want to do next time?”

This is best asked during an interaction with a guy that happens around an activity.

Your conversation might have led you to a bowling alley, archery club, arcade, or some other fun place. When you pop this question, it automatically assumes you’ll meet up again.

In a sense, it’s less of a conversation topic and more of a strategic move. If you like him and want to be more than friends with him, it’s critical to see each other regularly—and this topic helps you achieve just that.

#41: Talk About His Views on Sex and Dating

Speaking of being more than just friends with a guy you just met, you can steer the conversation in this direction if you’re feeling bold.

You can also ask him questions like: “What are your goals for dating?” or “What are you looking for in the dating game?”

Your honesty and openness about sex and dating will be refreshing to the right kinds of boys and intimidating to the wrong kinds. So try it out and see just how mature he really is.

#42: Your Views on Love and Romance

As always, expect your questions to be returned to you. So, be ready to talk about your views on dating, love, romance, and sex.

For instance, if you don’t like the idea of Marriage, you can say: “Marriage is nice, but I don’t think it’s for everyone. It certainly doesn’t appeal to me. What about you?”

Or, if you do like the idea of Marriage, you can tell him: “I think it’s sad that the dating world has become so promiscuous.

I think now, more than ever, people are throwing their relationships away like empty soda cans.”

You don’t need to be direct and upfront, but you do need to be true to yourself. Trust me—when it comes to romance and sex, you don’t want to give a guy you just met the wrong ideas.

#43: Your Previous Relationship Experience

This is a touchy topic, so use it with caution. Only talk about your previous relationships if you can manage to talk about your exes in positive or neutral terms.

Ranting about them to a guy you’re meeting for the first time will only make him feel uncomfortable.

Likewise, you can prod him a bit to tell you about his previous relationships—but if he’s avoidant, don’t push the issue.

Instead, take it as a sign that he might not be ready to reveal something so personal with you just yet. So, dial back, build more rapport, and see if he changes his mind later.

#44: What He Likes in a Woman

It’s a daring question, but if you feel the “spark” between you, it will steer the conversation in the direction you want. Ask him:

  • “Tell me… if you want to date a woman. 
  • What do you look for in her?”.

It’s a good sign when he can confidently answer that question. It means he’s comfortable with women, confident about himself, and knows how to get what he wants.

Meanwhile, if your question makes him unsure, insecure, or uncomfortable, he’s probably not all that experienced with women.

A disappointment, to be sure, but it’s best to avoid getting into a bad situation in the first place.

#45: His Idea of the Ideal Date


Another good “romantic” question is this one: “What’s your idea of a good date?” He’ll tell you his idea of an outing that’s fun for him. And when he does, you can say: “That sounds good. Maybe we should do that sometime.”

No matter how he reacts, it’s yet another tactic you can use to steer the conversation onto more romantic waters.

#46: Let Him Ask You Any Question

I hope you’re ready when you use this one. When you get to know each other, tell him: “Okay, just for fun. You can ask me any question, no matter what, and I’ll answer it. Make it good!”

This is a test of your confidence, but a test for him as well. Is he daring enough to ask questions that reveal your darker, naughtier side? Will he be able to deal with the racy answers you’ll give him?

If this topic makes him feel awkward or forces him to ask you a “safe” question, then either he’s not that confident or doesn’t feel familiar with you just yet. In that case, you can dial back for a while and some other time.

#47: His Celebrity Crushes

This question helps you understand the kinds of girls he likes. Ask him: “Who are your celebrity crushes?” and see if you recognize the names of the women he mentions.

If you want to get naughty, you can ask him: “Who’s your p*rn crush?” and see how confident and upfront he is.

It’s best to ask this in a hushed tone, of course—you don’t want the other café customers staring and waiting for his answer!

This can also help escalate things in a more flirty and naughty direction.

And it’s often a good idea to not wait too long to make things flirty/sexy. If you’re not compatible with each other, it’s not going to be worth it trying to make the pieces fit together.

#48: His Friends and Family

It’s best to reserve this one when you’re sure he’s “the one”—you want to be his girlfriend soon.

Then, ask him about his friends and family, and see how much he will reveal about the most important people in his life.

The best you can hope for is when he tells you a bit about his friends and family.

Then, he says: “I’ll introduce you to them soon.” That’s a telltale sign he likes you, too, and that he might want to be your boyfriend.

#49: Play The “Would You Rather” Game

This is a fun game to get to know each other better. For starters, you can ask him questions like:

  • “Would you rather have a million dollars, but you’ll age ten years, or become ten years younger?”
  • “Would you rather be an unknown superhero or a famous villain?”

You can later move on to racier questions like:

  • “Would you rather spend one night with your p*rn crush or get $5,000?”
  • “Would you rather have sex with one new person every year or just one person anytime you want for the rest of your life?”

This is also an opportunity to see if he can take the hint and move his relationship with you forward.

#50: Play “Never Have I Ever”


Lastly, you can play this fun group game, except one-on-one with him. Here’s how it works:

  • You both take a drink, preferably alcoholic, in hand.
  • Each of you tells the other something you’ve never done. For instance, you can say: “Never have I ever… gone skinny dipping.” And if he takes a sip of his drink, he has gone skinny dipping, and he must tell you something about it.
  • It keeps going until your claims (or drinks) run out.

 Some fun “Never have I ever” claims include:

  • “Never have I ever… kissed someone of the same sex.”
  • “Never have I ever… flirted with a teacher.”
  • “Never have I ever… played strip poker.”

And there you have it: 50 things to talk about with a guy. With the ideas on this list, you should have no trouble keeping a conversation going with a boy and even steering things in your desired direction.

And now, to wrap up, let’s cover a few “best practices” when conversing with men you just met.

6 Tips to Keep the Conversation Going with a Guy

How do you keep a conversation going with a guy? Aside from using your favorite ideas out of the list of 50.

The following six tips will help you keep things flowing with him—no matter what you’re talking about.

Master these six tips, and you’ll have the ability to have a fun, refreshing conversation with anyone on the planet.


Tip #1: Relax.

First of all, take it easy. Your worst enemy in carrying a fun conversation is attachment to a particular outcome. For instance, you might:

  • Want him to like you
  • Want him to make you feel good about yourself
  • Want him to fall in love with you and ask you out
  • Etc.

Yes, it’s good to have the desired outcome for your conversations with a guy. The 50 conversation starters in this guide will help you achieve that outcome, whatever it might be. The key is to not be emotionally attached to the outcome.

If you achieve the result, you want with him, that’s great. If not, it’s fine—he’s not the last guy you’ll meet, right?

So if you tend to be outcome-dependent, learn to relax and let go. You’ll be pleasantly surprised at how, ironically, you’ll achieve your desired results more often when you’re chill.

Tip #2: Make Eye Contact.

Eye contact builds trust with other people even when you’re not trying to.

When you look a guy in the eye, the same neuron activity in your brain starts happening in his, resulting in feelings of trust and—in some cases—attraction.

Of course, don’t make creepy eye contact, or you’ll make him uncomfortable. Instead, gaze into his eyes when he’s telling a story, when you’re asking a question, and when he says or does something you like.

Meanwhile, gaze out the window, observe the people around you, and glance at the ceiling when thinking of an answer.

Tip #3: Ask Open-Ended Questions

It’s a good idea to practice phrasing your questions to be open-ended—that is, they’re not answerable with a simple “yes” or “no.” For instance, instead of asking him, “Do you live in this town?” ask him: “What made you move to this town?”

Or, instead of asking: “Did you watch Money Heist?”, ask him: “What Netflix shows are you watching right now?”

Open-ended questions make for much better conversation fodder than close-ended ones, which helps to practice using them.

Tip #4: Give Compliments

Don’t hold back when he says or does something that impresses you. Compliment him. You’ll see him instantly warm up to you even more.

Why do compliments work so nice? Scientists have found that the parts of the brain that light up when we get a monetary reward also light up when we receive a compliment. That’s why compliments feel so good—and why you should consider giving them more freely.

Tip #5: Ask Follow-Up Questions

Let’s say you’re talking about your goals in life, and he tells you he wanted to work at NASA but was discouraged by his parents for being too “unrealistic.” At this point, you can—and should—ask a follow-up question or two.

You can ask him: “How did that make you feel?” or “What did your parents want you to do instead?”

Learn to linger instead of accepting his answer and jumping straight to the next topic. He’ll love you for it.

Tip #6: Don’t Be Afraid to Talk About Yourself

Lastly, most women think it’s ill-advised to talk about themselves with a man they just met, as it may make them look like a showoff.

You might be surprised to know that, in reality, it’s quite the opposite. Studies have shown that men will feel a much stronger connection with you if you talk about yourself during the date.

So, if he asks you to tell him more about yourself, go ahead. Your connection with him will make the conversation—and your relationship—much more enjoyable.