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How To Keep A Conversation Going With A Guy: 15 Foolproof Ways

How To Keep A Conversation Going With A Guy: 15 Foolproof Ways

You’ve finally started a thing with the guy you’ve been into for a while and you booked yourself a first date!

You’ve been texting back and forth and through social media, you’ve been having a great conversation.

It all seems potentially promising, but you’re going to be meeting him for the first time face-to-face and you’re dreading the potential awkwardness.

You wish you could keep having an interesting conversation – a witty text message is one thing, but what if he’s not a natural conversationalist?

What if the convo goes south and you realize you’re not exactly in possession of great conversation skills either?

Through text conversation, he seems like a worthy candidate, but what if in reality he doesn’t have a sense of humor? You couldn’t live with that.

What if he has zero interesting topics to discuss and makes you want to flake within 10 minutes? 

You’d rather let the wormhole eat you up than share an awkward silence one more time. 

Not being able to have a good conversation is a deal-breaker. If he can’t give you that, you’re going to have a hard time agreeing to a second date!

So now, you’re trying to figure out if there’s a way to keep the conversation going and avoid those dreaded silences as much as you can. Texting is cool and all, but can he keep up face-to-face?

God knows you can’t handle another shitty date, so you’d rather avoid dating altogether than suffer through another horrible blind date.

Those days are behind you and it’s time to find a good guy worthy of your precious time.

Good thing you’re here, then! Once you’re done reading this, the only problem you’ll be having is how to make yourself stop talking once you meet up! 

(And that’s a good problem to have.)

How To Keep A Conversation Going With A Guy?

It’s only natural to be a little anxious when meeting a guy you like, especially for the first time. You want the textual chemistry to translate to real life and there’s nothing wrong with that.

But it’s also important to realize that face-to-face conversation is much more challenging, so you shouldn’t put so much pressure on yourself.

This is a person who likes you just as much as you like him and he’s probably dreading the very same things!

And both of you are eager to make the best possible first impression, which puts an insane amount of pressure on both of you.

So my first piece of advice would be to relax and stop taking this too seriously or you’ll drive yourself mad.

This is not that complicated. If you click, you click, and if you don’t, there are no conversation starters that could save a zero chemistry type of thing.

But while you figure out if you’re vibing or not, there are plenty of excellent ways to give it a real shot.

And today, I’m going to be your own personal guide in helping you get your own life in love back on track and make this guy pine after you in no time.

There are some really neat open-ended questions you can start with that will help with the natural flow of the conversation.

You can always flirt innocently as you’re talking and distract him with your gorgeous looks.

Eye contact is crucial in keeping the conversation going (along with body language, but we’ll get into that later), as well as having a new topic to fall on if the first one doesn’t do the trick.

No pressure and an open mind are a powerful combination.

Don’t expect to become best friends turned lovers within hours. Chemistry takes time. If you’re both vibing textually, let it happen organically when you’re face-to-face.

Here’s how you can ease the atmosphere once you meet up, and keep the conversation going completely naturally yet effectively with just the right questions. Take a deep breath and relax. Here we go.

1. Don’t force it if there’s no conversational chemistry

First rule of how to keep a conversation going with a guy is to NOT force it if you’re not clicking and the vibe is off.

Remember. you’re not going to click with everybody you meet and that’s the most normal thing to expect.

Just like you’re not friends with every single person that has ever entered your life, you’re not going to find what you’re looking for in every guy you meet.

If the conversation keeps falling flat, you’re not feeling his vibe AT ALL, and the awkwardness could eat you alive, there’s honestly no resurrecting it from the dead.

Finish up the date, be polite, and excuse yourself as fast as you can. If you’re not feeling it, it’s not supposed to be. 

A simple conversation should not take SO much effort.

Sure, there is always a little bit of awkward silence as you’re breaking the ice, but eventually it’s supposed to get going and become easier as you go along.

If there’s absolutely nothing to go on, save yourself the trouble and call it a night.

2. Be genuinely into getting to know him

Don’t go into this wanting to make it all about you. You have to understand that this guy has dreams, ambitions, and hobbies you’re not necessarily going to be into, but that shouldn’t stop you from getting to know him.

You have to be interested in all aspects of him if you want to make it work and vice versa! So what if he’s insanely obsessed with video games, you have your hobbies too that I’m SURE wouldn’t be his cup of tea.

Let him win you over with his words and encourage him to tell you what makes him want to get up each morning. Get to know the dude. Find out what makes him tick and what his favorite thing in the world is!

That’s the basis of any great conversation. Let the other person share openly and be ready to engage in the conversation if you expect him to reciprocate.

Let him tell you about his favorite team (basketball or football, it doesn’t really matter) and talk about your favorite movies! And before you know it, you’ll be in a deep conversation completely smitten with each other.

3. Listen to understand, NOT to respond

This is a key thing in any good conversation. People are so busy waiting for their turn to talk that they only listen to reply, as opposed to listening to get actual information about the person.

Don’t be that girl. Don’t just sit around, waiting for your turn to talk.

Listen to him when he’s talking about something and always use the phrase ”tell me more” to make him feel like he’s not talking to a wall.

People need to feel like they’re being paid attention to.

Imagine how you’d feel if you were opening your soul to a person and all he does is nod his head and as soon as you’re finished he starts blurting out something about himself.

I’m sure that would make you feel so low and unappreciated. So make sure to never do that to a guy.

Listen, engage, and participate. That way, it’ll go both ways.

4. Ask him about his favorite things

You know how you just can’t shut your mouth when someone asks you about that one thing you’re deeply passionate about?

It just excites you too much and there’s so much you want to share!

The same goes for your first date with this guy. Let the conversation take you to a place where he feels totally comfortable sharing his passions with you and let him tell you all about it.

Firstly, it’s going to make him so happy to talk about something he genuinely loves. And secondly, it’s going to be so enjoyable listening to a guy you like talk about something with such joy and zest.

It’s definitely going to make you fall for him that much easier! 

And by doing that, the conversation is simply going to flow like a river.

You can exchange your dreams and share your experiences while encouraging the other person to feel relaxed sharing this with you, knowing you’re really that interested.

5. Don’t let the occasional silence discourage you

Yes, there will be occasional moments of awkward silence, It happens. It’s your first date and you’re literally just getting to know each other. Don’t expect miracles on your first try.

You’re not robots and at some point, the conversation is going to come to its natural end and you’ll be scratching your head for a few seconds in panic.

But guess what else? That doesn’t mean there’s anything wrong with the guy or that you should give up. It means that you’re human and you’re only starting up something together.

There will be bumps in the road and little hiccups now and again, but if the vibe is right and the guy is nice to be around, you’re not going to throw in the towel.

As the days go by and you’re getting more emotionally attached, it’s going to feel SO much easier filling in those pesky silent moments.

You just have to grow into it, like every couple does. It’s normal and if you’re really feeling this guy, keep working on it and don’t give up just when it’s started.

6. Repeat the last thing he said

Here’s a cool tip on how to keep a conversation going with a guy. If you’re struggling to find a new interesting topic to talk about, just repeat the last thing he said!

If he’s talking about some crazy adventures he was on or a dangerous hobby he loves so much, repeat the last sentence as if in disbelief.

He’s going to respond with a little smile on his face and expand on the topic. It’s such a silly thing but it works. It makes the guy feel like the man and it gives you a chance to come up with something interesting to say next.

This will him give him a push that he needs and make him feel like you’re not bored with his stories.

7. Ask him about his family background

Get to know him by asking about his childhood memories. But don’t pry too much. See if he’s willing to open up about it and if so, ask him about what he remembers from when he was young and what his upbringing was like.

Does he have siblings? Are they close and what do they like to do when they meet up? Do they live far away and is it hard being separated from them?

This will make him feel nostalgic and eager to share because who doesn’t get emotional and happy to share family stories about the people closest to him in the world?

This will keep the conversation going so smoothly that you’ll forget you’re on a first date and feel like you’ve known him for a while.

And when it starts feeling so homey and comfy being around him, you just know you’re with a good guy.

8. What does he do and does it fulfill him?

What does he do for a living? Is it something he dreamed of since he was a kid or was it a job he needed in order to pay the bills while he’s searching for something more in his lane?

Whenever the conversation starts fluctuating, you can ask him about work! Pretty much every adult person has a job and probably a million stories he could tell you about all of his work-related experiences.

Ask him about his favorite project he’s worked on and the one he hated the most. Does he have funny work anecdotes? Perhaps a funny colleague he does a perfect imitation of?

Maybe he’s the fun guy at the office who keeps the atmosphere light and joyful so you can ask him about his secrets.

Bottom line – there are a million and one work-related things you can discuss. After all, your job takes up half of your day! Surely, there are plenty of things to talk about there.

9. Share your own stories 

It’s a good start getting the guy to talk about him and his dreams in life. But don’t neglect yourself! He also wants to know everything about you so be prepared to open up as well.

Keep the conversation warm and pleasant by sharing light, fun anecdotes and stories from your life.

Tell him about your family, friends, and workplace. Share your awkward moments that will make you both laugh and let him know you don’t take life too seriously.

Be light and fun and don’t be afraid to make fun of yourself. That’s what guys look for in a girl.

Someone with a sense of humor who can laugh at themselves without taking anything personally.

Life’s an adventure and there’s no point being serious all the time.

A great conversation is born from fun, awkward anecdotes that release all pressure and make the other person feel comfortable enough to share their own.

10. Invite him with your body language

Body language is just as important as the words that are coming out of your mouth. If you look uninterested and closed off, the guy is going to feel rejected.

But there’s a simple solution there, too. For starters, don’t cross your arms as you’re talking as it feels like you’re being defensive and judgmental.

Rather keep your arms on your legs or in an open position where anything he says feels like it’s being received openly. 

Secondly, don’t be looking around the room as he’s sharing a story.

Keep straight eye contact (but don’t forget to blink, girl!) and make him see you’re there. Smile every now and then (nothing forced) and keep a relaxed posture.

This is not a job interview, you’re on a date with a guy you really like, so act like it.

It’s supposed to be chill and relaxed, so don’t give him the 20 questions treatment and let him talk as you’re carefully listening and looking him in the eye.

11. Leave an air of mystery

Don’t be too available too soon. Let the man want to get to know you more and more each time he sees you.

It’s good to share, but always leave a little something to the imagination. That way, he’ll keep coming back for more.

He needs to see that you’re an intriguing enigma that keeps on giving, but if he wants to know more, he’d better make an effort to get you to share.

It’s supposed to be a little playful situation where you both win. You keep him hooked with your flirtatious stories and conversation skills, but always leave room for more.

That’s an excellent way for him to get the sense of you and your quirky, flirty personality that will draw him in.

12. Avoid sensitive subjects early on

If you want to know how to keep a conversation going with a guy, let me tell you the first thing NOT to do.

Don’t get into sensitive subjects way too soon (ex-boyfriends, money, politics… you name it) and you’ll be well on your way.

People don’t want to hear all about your sad breakup story on your first date.

And this guy certainly didn’t invite you to dinner (or his place) to discuss politics and get into a heated discussion in case your views clash.

So scratch all that and keep it light, warm, and fun. That’s what the first few dates should be all about!

Getting to know each other and testing out the air. Seeing if there’s a click and if so, deepening your chemistry and having a good time together while your relationship progresses.

Such subjects (the aforementioned ones) are for later on when you’ve established what you are and already have that type of relationship where you can discuss controversial stuff without it affecting your relationship.

13. Don’t complain

The worst thing you can do is to make him think you can complain about anything.

Is that the first impression you want to leave? Instead of finding something to bitch about, find stuff that you can agree on and find common ground.

Leave the heavy stuff for later. This is your one chance to make the best impression, so use it wisely.

I’m talking from my own experience. Guys are truly put off by negativity and bitchiness. Leave him discover that side of you once you’re knee-deep in your relationship.

Be mindful of your habit of judging stuff you don’t really get. Be open-minded as opposed to judgy and critical.

The guy will not want to go on a second date if you’re nagging about all kinds of stuff.

It’s unappealing and you’re better than that. It’s all about light topics, positive vibes, and fun banter!

14. Ask him fun, thought-provoking questions

Pretend you live in a world where anything you wanted could become reality! Now ask him about the things he’d choose if he had a say in every single thing that happens from then on.

For example, if he could pick any place on earth to teleport to right now, where would he go and why?

If he could make any celebrity his best friend, who would it be? Would he change anything about himself if he could?

What’s the one food he’d have every single day delivered to his door if he could?

You get the gist. Live in a fantasy world and find out all about his likes and dislikes, preferences and things that put him off.

In a way, this will tell you everything you need to know about him. Give it a shot!

15. Throw in a compliment

Everyone likes to hear a nice thing about themself, that’s just a fact, and guys aren’t immune to this. Just because they act as if they don’t care to be complimented, it doesn’t make it true.

Keeping that in mind, find a genuine thing to compliment him on, and do it in a non-forced, organic way.

If when you’re talking, you notice how his dimples get so visible when he gives you an honest smile, tell him that!

He’s going to blush a bit, but he’ll be pleased to hear a compliment, especially about something he can’t even control!

And this could be a great conversation starter if you need one. Even if you’re texting, you can always share a genuine compliment and make the guy feel so good about himself.

Compliments never go out of style and they always help keep the conversation going. So keep that in mind next time you need a trick up your sleeve. It’s simple, kind, and very effective in disarming a person.

Final Thoughts

Finding a good guy to form a stable, mature, and fun relationship with is enough work on its own.

But finding a way to keep the conversation going during those first few dates is a completely different ball game.

Sometimes, your nerves get the better of you and you just freeze.

Other times, you’re so eager to say so much that you end up talking all over yourself and making zero sense.

And it’s all perfectly normal – expected even. So many women around the globe go through the exact same thing every single day.

And I’m here to wash away your worries and make you see that you’ve got this!

I’ve collected some of the most effective things you can take into consideration if you truly want to know how to keep a conversation going with a guy.

There are so many options out there, that I truly believe the only problem you’ll have is having too much fun exploring all these tips!

Dating should be light and fun, so always keep it that way. It’s not a job and nobody is grading you.

You’re there to find a guy who’ll compliment your quirky side and balance you out with his mild demeanor.

Try out these 15 awesome ideas and see for yourself that dating isn’t as bad as you have it pictured in your head!

It’ll be a fun ride, but not without its bumps in the road. So remember, just because it isn’t smooth sailing, it doesn’t mean it isn’t right.

The best things in life require effort, time, and patience.