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Dating A Shy Guy: 33 Key Things To Know Before Dating Him

Dating a shy guy can have its difficulties, but all in all, it’s amazing.

Why is dating a shy guy amazing? Because this is finally someone who will really listen to you.

A date with a shy guy will be different from the ones you’re used to. A shy man is not one of those guys who likes to brag and talk about themselves.

It will be hard to get to know him better, but it will be worth it because you’ll always find out something new about him.

There are many benefits of dating a shy guy, and you’ll learn them in this article, along with how to start dating a shy guy.

If you’ve never been with such an introverted man, this is going to be a whole new experience for you and I could give you a lot of reasons why you should date a guy like this.

For instance, a shy man wants to be out of his shell, and he’s not afraid to show his vulnerable side.

Dating a shy guy is basically dating a quiet guy, but the silence is never awkward, it’s actually comfortable.

Still, getting a date with a shy guy isn’t an easy task and you’ll most likely have to make the first move with him. 

These tips on dating a shy guy will make that easier for you because you’ll get to understand him better.

You’ll learn how to date a shy guy, and you won’t regret it.

Dating a shy guy: 33 key things to know before dating him

Dating A Shy Guy: 33 Key Things To Know Before Dating Him

There are a lot of silences when dating a quiet guy, but it doesn’t mean he won’t communicate, it’s just harder for him to express himself.

Once you learn how to date a shy guy, you won’t have such a problem with his shyness.

You’ll learn how to deal with it, and dating a quiet guy might turn out to be the best relationship you ever had.

Let’s get right to the tips on dating a shy guy. These tips on dating a shy guy will help you figure him out and make your relationship work.

How to date a shy guy

1. Take it slow at first

Dating A Shy Guy 33 Key Things To Know Before Dating Him

When you start dating a shy guy, make sure not to bombard him with a lot of details about yourself; it could make you seem intimidating, and you want to avoid that.

Another tip is not to monopolize the discussion.

You can try getting him to participate by asking simple questions.

“The weather’s pretty crazy these days, am I right?” might be simple, but it’s not as scary as, “When do you plan on having kids?”

2. Work on building trust

Dating A Shy Guy 33 Key Things To Know Before Dating Him

When you start dating a shy guy, it’s essential to show him that he can trust you.

You need to prove that you are a trustworthy person, and you do so with your actions. Once you develop trust, he will start to open up to you.

Be careful not to break the bond you have created. For instance, if he tells you a family secret, don’t let it slip out when you’re talking to your friends.

If you make him a topic of gossip, it will break his heart, and he will close himself off.

3. Don’t ever make fun of his shyness

Dating A Shy Guy 33 Key Things To Know Before Dating Him

He is probably trying to overcome his shyness, and the struggle is real for him. Making fun of it or discussing it in a public place is not okay.

Perhaps he is suffering from social anxiety because of bad past experiences, and it’s not a joke.

So, you need to accept him the way he is.

If that seems like too much for you, maybe he’s just not the right man for you but keep in mind that with a little positivity and practice, everything can get better.

4. Come up with fun questions for him

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Most of the time, dating a shy guy means that he won’t just hand you the information – you’ll have to dig for it.

Forget about serious conversations and think of some fun questions that could start a discussion.

Everyone loves entertainment, and it gives you plenty of opportunities to get him to talk about it.

What was his favorite childhood cartoon? What is the book that has influenced his life the most?

What’s the worst movie he has ever seen? He won’t feel like you’re putting him on the spot because these questions require some thought and the best thing is that you’ll learn more about his interests and hobbies.

5. Go to the movies

Dating A Shy Guy 33 Key Things To Know Before Dating Him

This is an excellent idea for a first date because it allows you to spend a few hours together without having to talk too much.

It’s perfect for when you’re dating a shy guy, and it’s more original than grabbing drinks together.

You will share not only popcorn but an experience that you can talk about later.

Even if the movie you saw was terrible, it will give you something to laugh about on your way home.

The most important thing is to make sure that he is comfortable.

6. Plan the details of your date and tell him from the start

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Dating a shy guy is harder for the guy than it is for you as he will be home worrying about everything that could go wrong on the date and that might make him even more reserved when the date actually happens.

Don’t worry though, because there’s something you can do about it to make all this more comfortable for him.

You do that by taking the initiative and preventing things from going wrong before the date even starts.

Open up and be friendly about the elements of your date that he could be concerned about.

It could be simple, like saying, “I would like to split the cost of the date with you,” because it will help him not be anxious when he gets the bill.

You can come up with a game plan for the whole date, and it will make it less stressful for him.

So, if you have an idea like grabbing ice cream after you’re done with dinner, tell him about it upfront.

Of course, you won’t have to keep doing this for the rest of your dates, but it’s essential when you’ve just started to date.

7. Listen carefully to what he has to say

Dating A Shy Guy 33 Key Things To Know Before Dating Him

When a shy guy opens up, it’s a huge step forward and that is why you need to be a good listener, ask follow-up questions, and avoid interrupting him.

Do your best to really hear him, engage in what he’s talking about, and learn something from it.

This is an excellent skill to have regardless of who you’re dating, but it’s especially crucial with a shy guy.

Make him feel valued, and he’ll appreciate it; after all, he will always listen carefully to you, so it’s only fair that you do the same.

8. Don’t talk about his shyness

Dating A Shy Guy 33 Key Things To Know Before Dating Him

There’s no reason for you to mention his shyness in front of him so don’t ask questions like, “Will you be okay if there are a lot of people there?”

You can find ways to make him feel comfortable without mentioning his shyness.

Of course, later on, once you’re in a committed relationship, you can talk about this, but right now it is best not to.

If you have only just started dating, he won’t be comfortable talking about it, so don’t scare him away.

9. Use his interests to start a conversation

Dating A Shy Guy 33 Key Things To Know Before Dating Him

This is not the type of guy who opens up to others easily.

Before even talking to him, you must make sure that he feels comfortable around you so when it comes to communicating, start a conversation about something he likes.

As soon as he gets comfortable talking about those topics, he will relax and once he’s calm, you should let him open up to you.

10. Don’t ask questions that he can answer with a yes or no

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Closed-ended questions are your enemy when you’re dating a guy like this.

If you ask questions that can be answered easily with a yes or no, you won’t have a conversation.

Keep this in mind and ask questions that demand him to respond with more than one word.

For example, if you want to ask him whether he wants to join you at the mall, ask him to suggest something you could buy there.

You can use this little trick with just about any question; the goal here is to get him to talk as much as possible.

11. Use the fact that shy guys thrive on texting

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Choosing a topic to talk about is one thing, but choosing a way to communicate is also important.

The thing about shy guys is that they feel more comfortable with texting than with talking; it gives them some time to think about what they will say, and it comes with emojis.

So, use texting as a way of communication that he’s most comfortable with.

Another advantage of this is that you don’t have to talk when you’re tired. Let him type his feelings and send it to you as a text if that’s easier for him.

12. Don’t rush him

Dating A Shy Guy 33 Key Things To Know Before Dating Him

The person you’re dealing with is an introvert and what that means is that he might not be as spontaneous as you are.

Maybe you think that it’s perfectly normal to do something out of the blue just because you want to do it, but that’s not so simple for him.

This is the type of guy who needs time to consider what he will say or do next so take it slow and let him do things at his own pace.

13. Be patient and enjoy the silence

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Dating a guy like this will require patience.

Even though the silence is comfortable most of the time with a guy like this, sometimes it could be awkward for you but he will actually be using that time to process his next move.

It’s important not to ruin that by saying something unnecessary. Those silences are special, and you’ll learn to enjoy them as you get used to it.

Keep in mind that it’s not awkward for him because he is always like that.

14. Give him compliments

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Appreciate his wit, his appearance, and all his gestures that have moved you. Who doesn’t love compliments?

This is something that is no different when you’re with a shy guy.

He wants to understand what you like and don’t like and giving him a chance to do that will make him talk about his preferences as well.

15. Learn to accept the way he expresses himself

Dating A Shy Guy 33 Key Things To Know Before Dating Him

So, maybe you have bought a new dress, especially for this date.

Naturally, you’re yearning to hear him praise it but all you get is a simple, “That’s different.”

This is not the response you had been hoping to hear, but you can’t expect a lot of words from a shy guy.

Don’t show him that you’re disappointed by his response. You have to learn to accept the way he expresses himself if this is going to work.

16. He needs space

Dating A Shy Guy 33 Key Things To Know Before Dating Him

You can’t expect any guy to spend all his free time with you, let alone a shy one.

Like all guys, he needs space, and since he’s an introvert, he’ll need more alone time. Let him do his thing, even if you’re hanging out at his place.

You need to understand that a guy like this needs this alone time so let him have his space and don’t pressure him to spend every waking hour by your side.

17. Be by his side when you’re in a crowd

Dating A Shy Guy 33 Key Things To Know Before Dating Him

A guy like this isn’t very comfortable being surrounded by unknown people.

He is an introvert, so he is easily intimidated by a large crowd but he can work on overcoming this social awkwardness, and you can help him do that.

Talk to him about things he is comfortable discussing and stay by his side when you’re in a crowd.

If you notice he’s feeling uncomfortable, find a way to leave.

18. Always accept his romantic gestures

Dating A Shy Guy 33 Key Things To Know Before Dating Him

When a shy guy gives you compliments or gifts, don’t criticize and instead accept them.

He has put effort into picking a romantic gesture he thinks best describes the way he feels about you, which proves he cares about you, and is trying to show you that.

So, just accept it. If you don’t and make negative comments instead, he’ll form an analysis of what exactly went wrong.

In the process, the moment will pass, and you’ll just lose something that could have been romantic.

19. Don’t make him feel like he’s being interrogated

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Your constant questions could sound like an interrogation.

If you have spent some time together, and he still won’t open up about something, stop asking questions about it.

For instance, if he doesn’t want to talk about his family, respect his decision.

If he really loves you, he’ll tell you about it when he’s ready.

There is no point in rushing him and the only thing your interrogation will achieve is to distance him.

20. Make sure he knows you like him for who he is

Dating A Shy Guy 33 Key Things To Know Before Dating Him

What is being an introvert?

Like so many other things, it’s a personality trait, and there’s nothing bad about it; as a matter of fact, it could be considered as something positive.

So, don’t think that he’s weird just because he’s shy.

Make sure he knows you like him for who he is; after all, he’s a guy like all the others, he just does some things a little differently.

Tips on dating a shy guy

1. He won’t interrupt you

Dating A Shy Guy 33 Key Things To Know Before Dating Him

And that will feel good.

You’ll feel like you finally have someone who actually listens to you and cares about what you say and the ability to talk without being interrupted will make you feel great.

2. He isn’t quiet because he’s mad

Dating A Shy Guy 33 Key Things To Know Before Dating Him

You know how some people get really quiet when they are passive-aggressive?

Well, this guy isn’t quiet because he’s mad about something, he’s just that type of person so enjoy those silent moments without the fear that you’ve done something wrong.

3. You have to ask him questions about himself

Dating A Shy Guy 33 Key Things To Know Before Dating Him

When something happens, don’t expect him to tell you all about it. It’s not because he’s hiding something from you, he just isn’t much of a talker so if you want to learn more about him, you’ll have to ask him questions.

4. You’ll constantly learn new things about him

Dating A Shy Guy 33 Key Things To Know Before Dating Him

There is a great benefit to him being so quiet.

Because this guy won’t open up so easily, you’ll find yourself constantly learning something new about him for as long as you’re together.

Some people put all their cards on the table at the start, but a shy guy will let you enjoy the card game.

5. He’ll ask questions too

Dating A Shy Guy 33 Key Things To Know Before Dating Him

And they will most likely blow your mind because they’ll prove how much he has been listening to you and don’t be surprised when he asks a big, meaningful question that you didn’t think of yourself.

It could be something philosophical, like, “Will you ever be truly happy if you never reach that goal?”

6. He is too good of a listener

Dating A Shy Guy 33 Key Things To Know Before Dating Him

He is a good listener, that’s true, but sometimes he can be too good.

Since he remembers everything you say, it will be hard for you to change your story.

For instance, if you lied about something when you first started dating, it’s bound to come out sooner or later.

7. He might not get along with your friends at first

Dating A Shy Guy 33 Key Things To Know Before Dating Him

This type of person doesn’t feel comfortable with a large audience; they are much more up for one-on-one hangouts.

So, when you introduce him to your friends, maybe it’s best to introduce them one by one.

Don’t be alarmed if he doesn’t get along with your friends at first, because that will change once they stop being strangers.

8. You will love his friends

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Who is friends with a shy person? Usually, it’s the kindest, most patient person who chooses a person who’s standing alone at a party.

You won’t feel awkward around them because they’ll accept you just like they accepted your shy boyfriend.

9. You’ll get irritated by loud men

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Once you get used to this silent guy, loud guys will start to seem annoying to you.

You don’t want someone who’ll yell at the screen because of some sports score.

Once you get a taste of what being with a shy guy is like, you won’t want to go back to the loud men you dated before.

10. Is your man’s quietness his weakness?

Dating A Shy Guy 33 Key Things To Know Before Dating Him

Well, you’ll get protective any time anyone says that but don’t get worked up about it; after all, guys think a lot of stupid things are masculine, and they couldn’t be further from the truth.

You can’t blame them though’ just like girls are obsessed with looking pretty, guys are obsessed with looking masculine.

11. He’ll be good in the bedroom 

Dating A Shy Guy 33 Key Things To Know Before Dating Him

I don’t know what it is about shy guys that makes them so good in bed, but they are.

12. You’ll fall for his shyness

Dating A Shy Guy 33 Key Things To Know Before Dating Him

You’ll fall in love with his shyness more and more every day and this is because you’ll know that when he starts stuttering or gets nervous around you, it’s only because he likes you so much.

There will be some awkward situations in which you’ll really see what a sweet and gentle spirit he is.

There’s nothing cuter than a guy who acts weird just because he’s madly in love with a girl.

13. You’re probably shy too

Dating A Shy Guy 33 Key Things To Know Before Dating Him

The reason why you’re with this guy in the first place could be that you’re a little shy as well.

Sure, you talk more than he does, but if you had never felt like he does, you wouldn’t understand him the way you do.

Now that you know all about shy guys, enjoy dating one and see if I’m right about all this.

If you have learned anything from this article, it should be that shy guys are great partners, so enjoy your amazing love life!

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