In your constant pursuit of tall, dark, and handsome Casanovas, you often neglect to see the unique benefits of dating a shy guy!

Your first date with a shy man might not exactly be a walk in the park, but if you’re willing to make the first move and follow my brilliant tips, you’re in for a fun ride.

Let’s be real for a second. How many times have you been burned by a hot, mysterious, show-off who ended up being a lot more than you bargained for?

For me, the number is almost limitless. So let’s switch it up. Let’s start seeing the amazing potential of the quiet introvert next door.

Let’s take the lead and start giving kind, shy dudes a chance to show how cool they truly are. Because they can, and most likely will surprise you!

First, take a look at these super handy tips, after which I share why you should definitely give a shy guy the benefit of the doubt!

How To Date A Shy Guy: 20 Brilliant Tips

Don’t focus on his quietness from the get-go

Focusing on his introverted side from the start is the wrong move. Instead, try to make a comfortable environment to hang out where he’ll feel at ease.

People with social anxiety don’t really want to discuss it at length. Your best bet is to observe his body language and see how he responds to your efforts.

Shy guys are really good listeners, as long as you gradually ease him out of his comfort zone. Whether it’s a dinner date or just coffee, don’t be discouraged if there are awkward silences.

That’s perfectly normal for any date, let alone with a shy guy. Take the lead, initiate the conversation, and make eye contact.

The easier you make it on him, the better your chances of success. Face-to-face engagements can lead to some awkwardness for him, so it’s on you to break the ice.

 

Ask him open-ended questions

With extroverts, it’s pretty chill. The conversation is most likely to develop organically as there are no issues with self-esteem on either part.

But with a shy guy, you’ll need these dating tips more than you know. Even if it’s a guy you‘ve known since high school or you’re just meeting him for the first time, focus on how you approach the conversation.

Ask him open-ended questions that won’t give him the chance to just reply yes or no. That way, you’ll allow him to introduce you to his world a bit without being pushy.

Shy guys (and shy girls) have a hard time opening up, so give him a break. He may not be the one to ask you out, but if you do this the right way, soon you’ll be considering date ideas for round two!

Be a little flirt, “trick” him into revealing more than he intended (oops), and watch things develop at a surprisingly great speed.

 

Find common interests and lead with that

Your first task is to search for common interests (perhaps you could ask his sibling, best friend, co-worker?) so that you’re prepared.

I know this sounds so robotic, but I promise you, it isn’t. With an introvert, it’s vital to make it as comfortable as possible ASAP, or their interest will wither.

By doing some research, you’re simply ensuring that there’s enough to talk about without awkward moments of quietness right from the start.

Maybe you like the same genre of music? Or maybe you’re both super into dogs? Find out, don’t be shy to introduce the topic, and things should go fine after that.

 

Figure out his preferred way of communication and stick to it

Does he prefer face-to-face conversation or does he maybe feel more comfortable over social media?

If it’s the latter, perhaps you could send him a funny photo on Snapchat and have some banter that might turn into an actual conversation?

But if he’s more into real-life interaction, then don’t be too overbearing with a constant barrage of texts. To you, it might be nothing, but to him, it could be a deal-breaker.

Basically, just feel it out, and once you think you’ve figured out how he prefers to communicate, stick to that.

 

Don’t feel the need to fill every silence

And there’s a very good reason for that. You see, when dating a shy guy (or starting to date him), you need to have patience. A lot of it.

These guys won’t just blurt stuff out and see how it goes. For him, it might take a few seconds, or more, to formulate what he wants to say. Don’t question his ways, but just give him a chance to say it.

Even if it means enduring some quietness for a few seconds. Because if you keep filling every single silence, how is he ever going to say anything?

If you’re willing to bear with him and take things super slow at the start, it truly might be worth your while. He could be a real romantic, you just have to let him show you at his own pace.

 

Don’t expect a lot of spontaneity on his part

Remember, you’re dealing with an introvert. And they’re not exactly known for being the initiators of anything. And that’s okay.

During the first stages of dating, do most of the heavy lifting and don’t expect him to woo you off your feet with grand gestures. Is that really what you want?

Or do you prefer a good listener with a kind heart who won’t constantly talk over you? Because this guy could be a real daydream. Just because he’s not flashy, doesn’t mean he’s not worthy.

Most of the guys I used to date were smooth-talking extroverts, and let’s just say it never led anywhere good.

But with an introvert, there’s this peace of mind that overcomes you with time, and it simply can’t be replaced.

 

Be upfront about your keen interest

He might not exactly pick up on your subtle signals since he’s not the most extroverted guy ever. So you’re going to have to be upfront.

If you like something about him, openly tell him, don’t assume he’ll figure it out. If you keep things to yourself, he’s just going to overthink everything.

If you enjoy his company, by all means, share it with him. This guy wants to know how you feel, but he’s not exactly going to ask you, now is he?

But that’s kind of the beauty of dating a shy guy. There are no mind games, no tricks, and no need to doubt yourself. The cards are on the table, which makes it all so simple.

 

Ask him about his family and childhood

This is a wide-ranging subject that might get him talking, and it’s just the right amount of personal.

Without expecting an intimate recount of every aspect of his childhood, go with the basics. Ask him where he grew up, whether he has siblings, and what his relationships with them are like.

Ask about his parents, what they do, and if they live far away? Every single thing he shares could be a prelude into a new conversation.

The trick is to listen to understand, not merely to reply and move on. In order to develop a meaningful conversation, you have to be a good listener.

 

Just because he seems underwhelmed, doesn’t mean that he is

Let’s say you’re on your third date, and you’ve just got a new haircut. It’s quite a change and one would have to be blind not to notice it. But he doesn’t.

And you’re kind of perplexed. You feel good about yourself, it’s edgy, cool, and totally unexpected, yet he says nothing.

But that’s just his way of expression. Just because he’s not lauding your new cute do, doesn’t mean he doesn’t like it. He’s just not the type of guy to proclaim it openly.

If you really care about his opinion, ask him what he thinks! Chances are he likes it but was just hesitant to say anything first. Give him a little nudge and it’ll be okay.

 

Never share anything he tells you in confidence

It’s crucial that you be a woman of your word. If he has broken out of his shell and shared an intimate aspect of his life with you, safeguard it no matter what.

It means so much more than you actually think. Shy guys are really difficult to crack. You seldom know what’s on his mind, and he won’t exactly jump at the opportunity to blab his mouth.

So if you’re familiar with something not a lot of his close friends are privy to, consider it an enormous privilege. This is a sign that he’s starting to feel a deep connection with you.

And if you prove to be a good confidante, your bond is only going to become stronger over time.

Don’t rush introducing him to your friends and family

If there is one thing shy dudes don’t like, it’s big audiences. That only creates an unnecessary amount of pressure that doesn’t allow them to feel comfortable.

So hold off on the introductory parts. You want to do this the right way. Take it slow and don’t even mention such serious topics unless you feel he might be okay with it.

And remember, if he feels hesitant or seems anxious about the prospect of meeting your friends, it’s not personal. That’s just who he is.

Wait until he’s fully comfortable with you that you can broach this subject, knowing he could actually be up for it. And once this moment comes, choose a place of his liking.

 

Be extra mindful to give him enough space

In any type of relationship, it’s so vital that both partners have enough breathing room. Alone time is super important for introspection and recharging.

But with an introverted individual, it’s double the amount. So be sure to let him just be. Don’t constantly text, call, or expect him to spend all of his free time with you.

This dude needs his alone time more than you know. That’s his escape from the real world and everything he has to put up with daily.

Be considerate of this and don’t crowd him when he’s clear about his need to just chill on his own. The more space you give him, the more into you he’ll be.

 

If he’s into cozy nights in, there’s nothing wrong with that

I once dated a shy man who wasn’t really big on dinner dates at fancy restaurants. He would always feel anxious and overwhelmed whenever we were in rooms full of people.

That just wasn’t his scene and it took me some time to accept that. It wasn’t that he was cheap or that he was ashamed to be seen with me. He simply preferred a snuggled night on the couch.

And honestly, aren’t those types of low-key nights the best? There is no pressure to look your best, and you can just totally relax, order takeout, eat your face off, then cuddle over a movie.

If you ask me, cozy nights in are the new fancy dinner date! If you can be perfectly content just spending the night together doing nothing, then you’ve got an actual shot of making it work.

 

Help him overcome his social awkwardness

Dating a shy guy might mean having to hold his hand in a busy street. It provides him with a sense of relief knowing you’re simply there.

I can’t possibly pretend to understand how introverts feel since I’m not one, but I will always do my best to be as considerate as possible.

I strongly encourage you to do the same. Be his rock. Hold him down when he’s ridden with anxiety. Show him you’ve got his back and you’re not going anywhere.

The moment you sense he’s starting to feel even slightly uncomfortable, find a good excuse to get out of that situation. Read his body language and you’ll make life easier for him.

 

Silence your inner critic

After a certain amount of time with someone, we start to develop this sense of freedom to speak our minds. This means that you’ll find it easy to tell your boyfriend off for something silly.

And in most cases, that’s really good, as it shows that your relationship has significantly progressed and reached one of the ultimate stages.

But when dating a shy guy, you’re going to want to be careful with that. There will definitely be times when you’ll want to criticize him, but stop to see it from his point of view.

Reevaluate the importance of your complaint, then try to word so that he doesn’t take it personally. Ease him into this new, unique aspect of your relationship.

 

Be willing to take baby steps

Rushing into things almost never amounts to anything positive. At least it doesn’t for me. So this may as well be a true blessing in disguise.

To be perfectly honest, yeah, at times, it may seem as if it’s taking forever to reach a new level of intimacy. It may seem as if he’s not as invested as you are.

But that’s just dating a shy guy, you know? By now you must’ve realized that his lack of speaking up and initiating things doesn’t mean that he’s not exactly where you are.

It’s just that it might take him a bit longer to transcend your current level of romance. Clearly, he enjoys spending time with you. Just give him time to move at your desired pace.

 

Never use his shyness against him

Sometimes, in the heat of the argument, we all say things we don’t necessarily mean. Now imagine saying something nasty to a guy with social anxiety that you definitely don’t mean.

You’ll be arguing, throwing insults, and all of a sudden, you’ll mention how difficult it’s been for you trying to acclimate to his introverted lifestyle.

That’s not something he’ll just get over. It’ll hurt him like a thousand knives in the chest. His shyness is part of him. He doesn’t choose to be this way.

So when you use this against him (even if you don’t really mean it), to him, it’ll be soul-crushing and devastating.

 

Don’t pressure him to open up

If there are still some aspects of his life that he’s unwilling to talk about with you, don’t interrogate him. Don’t be that person who just can’t leave things be.

It’s okay if you’re not privy to every excruciating detail of his life. There is still so much time to discover new things about each other.

I bet that you haven’t exactly disclosed every single dirty secret to him, have you? So leave it be. He’ll share when he feels like it. Pressuring him will only be counterproductive.

Be chill and let him do his thing. He’ll appreciate you not being pushy, which can only be beneficial for your relationship.

 

Be willing to make plans yourself

Part of dating a shy guy means making arrangements and taking care of things he might feel hesitant to. It’s really not a big deal.

Most times when you hang out, you’ll be the one to suggest when or where to meet up next. It’s as simple as that.

It alleviates any unnecessary pressure off him and also allows you to surprise him with something you know he’ll like. Taking charge isn’t so bad.

Plus, with time, he’ll become more comfortable sharing the spotlight.

 

Appreciate him just the way that he is

Just to be clear, there is absolutely nothing negative about being shy. We’re talking about a personality trait that actually carries lots of positives!

A shy guy can be your soulmate – you just have to let yourself see it. And how are you going to do that? By appreciating this guy exactly the way he is, of course!

By never expecting him to be someone you want, but rather allowing him the freedom to live his authentic life by your side. There is nothing weird about being shy.

He’s just a normal guy who could take your breath away easily. The only thing is that it might take him a bit longer. But so what?

He could end up being such a romantic at heart and surprise you in more ways than one. All you have to do is let him be his cool, unique self.

Why Dating A Shy Guy Is Amazing

  • He is an excellent listener. He won’t talk over you or interrupt you mid-sentence. You will always have his full attention and, unlike most guys, he will genuinely care about what you have to say.
  • He is modest, sincere, and doesn’t need to be in the center of attention. He keeps his circle small but abundant in quality. Being kind and humble is what he is all about.
  • He isn’t interested in toxic mind games. And that is the most refreshing thing in the dating world if you ask me. In a sea of superficial show-offs, his sincerity will stand out.
  • He is more likely to be understanding of your problems. And even better, he will offer helpful solutions and genuine advice. This guy cares about your soul, not just your body.
  • He will never pick at your flaws. He will appreciate every single imperfection, quirk, and shortcoming. He will never dissect your appearance or make you feel unworthy.
  • He will always be his raw, authentic self. He’ll always tell you like it is. He isn’t interested in projecting who he’s not. With him, what you see is almost always what you get!

 

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