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Dating a Shy Guy – 27 Pros and Cons You Should Know

If you find yourself dating a shy guy, you must be special to him! Shy guys tend to avoid putting themselves out there, so it's likely that he has a genuine connection with you, and that you’re the only one he’s dating.

But talking from experience, you can often meet some obstacles when dating a shy guy. 

Being shy isn’t always simple and can often mean a number of different things. Shyness and mental complexity can often go hand in hand, meaning that there’s a lot for you to understand to be able to make things work with him.

According to James E. Johnson, co-writer of the article ‘Attributions of shy persons in romantic relationships’, “shy females may be more committed to making a relationship work, whereas shy males may be more willing to abandon a problematic relationship.” 

This means you really have to put effort into making this relationship work. To understand how to accomplish that, it’s important to establish both the pros and cons of dating a shy guy. 

Pros of Dating a Shy Guy

1. You don’t have to worry about them flirting with other girls

This one is a huge bonus, but obviously cannot be guaranteed. It’s simply more unlikely for your shy boyfriend to be disloyal because he is likely to be reserved by nature, meaning two things: number one, he’s not looking for anybody else, and number two, he simply can’t tell when someone is flirting with him.

This isn’t something to take advantage of, and is one thousand percent something to cherish and appreciate in him. It can be extremely difficult to put your complete trust into somebody, so when you do, vocalize it and don’t take it for granted.

2. You can trust that you have genuine connection 

It can be difficult to know how genuine your connection is with somebody when you start dating. You can never really tell if they’re into you as much as you’re into them and this can often feel confusing. 

But, when dating a shy guy, if he’s gone out of his way to date you then he’s probably in it for the long game!

A shy man will tend to avoid putting himself out there, as it can be difficult for him. So, just know that if he’s stepping out of his comfort zone to date you, then it’s likely that he feels a genuine connection with you.

3. It will naturally boost your confidence

You will often step out of your comfort zone for the both of you, meaning that you are naturally going to improve yourself and your confidence socially.

4. You will grow together

you will grow together

The best part about being in a relationship with someone who is a lot more shy than you is that you will watch each other grow. 

In relationships, we naturally sort of merge with one another and this isn’t always a bad thing. You’re going to learn from his shy and reserved nature and in time his confidence will improve simply by watching you! There’s nothing more romantic than changing each other for the better.

5. The sex could be amazing

All I’m saying is… It’s always the quiet ones.

I think I’ll leave that one there for you to think about ladies.

6. You’ll spend a lot of time as a couple

Quality time together is always a good thing. You’re likely to have more quality time together due to his shy nature, you won’t socialize too much as a couple meaning that you’ll spend a lot of time in the company of one another. 

7. He’s probably a good listener

Shy men are often great listeners, and you’ll most likely always know where you stand with him. I’m talking no game playing, just a good and honest connection based on getting to know each other. 

8. He won’t have too many exes

The number of exes somebody has can often be daunting. It’s something that we shouldn’t care about, but we often can’t help it.

Having a shy boyfriend means that he probably hasn’t had many partners before. This is because he will spend the time developing genuine connections with people, and will only go at his own pace, meaning that he doesn’t have a past of rushing into things.

9. He probably finds your confidence sexy 

As a shy person, it’s perfectly normal to admire people with an opposite personality trait. It’s likely that he will be envious of your confidence, but also in awe of it.

Cons of Dating a Shy Guy

As much as there are many positives to dating a shy guy, there are also some obstacles that you can come across in the relationship.

1. He may have poor communication skills

Shy guys often struggle to communicate because it’s something they’re likely to have avoided for their entire life. 

Whether it’s positive or confrontational, he’s probably going to struggle. This can be challenging, especially if you’re a very open person who is honest about their feelings. 

2. It can feel hard to get to know him

In the early stages of dating, it can be extremely hard to break down his barrier, and so it can take a bit longer to get to know him. 

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Your first date will probably consist of an awkward silence or two, and then in the first few dates he will gradually open up. This can feel difficult, especially if you’re a very open person; you may feel like you’re asking a million open-ended questions but that you’re not really getting anywhere. 

What it really comes down to is establishing chemistry or a connection between the two of you. Once established, the rest will come in time.

3. He could be inexperienced

As mentioned, it’s likely that he doesn’t have a lot of exes, which can be great. But, it can also mean that he’s not had much experience when it comes to relationships.

This can impact several things: sex, communication, socialization, and in general how you should be treated in a relationship. You will most likely have to step up and be very vocal about your relationship needs in order to get through to him. 

4. You often have to step up

Social anxiety is common for shy men, meaning that when you’re out in public you will often have to step up. 

If he isn’t vocal about his social anxiety, you can usually tell by his body language or behavior. If his body language communicates that he’s feeling shy (for example, a closed posture or keeping his head down), then you often have to step in and take over. 

This may be something as simple as placing an order in a restaurant or even stepping into a conversation in a social setting that he is clearly struggling with.

5. Socializing together can be difficult

socializing together can be difficult

His shy side will really come out when socializing, especially if it’s not with his close friends. This one is kind of a deal breaker; you want your boyfriend to click with your friends and family at the end of the day, and his shyness might make this incredibly difficult. 

6. You will often have to initiate sex 

Having to initiate sex constantly can be really difficult on your confidence and self-esteem, but if you’re dating a shy guy he’s most likely not going to make the first move

Even for something that might seem as simple as your first kiss could be incredibly overwhelming for him, meaning that you have to combat his social awkwardness by stepping up yourself. 

7. You could disagree a lot

It may be hard to agree on things due to your different personality styles. This could be as small as agreeing on a date night activity, or something as big as not liking each other's friends. 

Once you get comfortable together, he won’t be shy with you any longer, but he will be to the rest of the world. This is where you might begin to disagree. 

There is no problem with disagreeing with your partner, however if you disagree on almost everything, you’re going to end up facing a problem or two.

8. Don’t expect grand gestures 

He will give you subtle hints of affection, but grand gestures are something that he’s most likely not capable of. 

Shy people often struggle to communicate and show affection. This can be good as it can mean that you’ll develop your own love language, however until you fully understand one another, you can be left feeling slightly underwhelmed in the relationship.

Tips for Dating a Shy Guy

There are many pros and cons to dating a shy guy, just like there are when dating pretty much anyone. However, there are many ways to overcome problems when dating a shy guy, and what it mainly comes down to is fully understanding each other

1. Make the first move

In reality, you rarely want to make the first move… You want to feel adored and wanted by somebody showering you with love and affection. 

But if you see yourself dating a shy guy, then it’s probable that you’ll have to make the first move. He won’t feel comfortable enough and might need a little nudge.

2. Communicate

This is the most important rule in any relationship, but is especially true if communication is something that your partner struggles with.

If you encourage communication with your partner, and are as honest as can be about your feelings, worries, or relationship needs, then you’re off to a pretty good start.

Talk through your problems, ask him to tell you when he is feeling anxious or shy as it’s not always obvious from his body language. Spend time understanding how to respond to certain situations impacted by his shy behavior. 

3. Be open about your feelings and encourage him to do the same

We’ve already established that he’s going to struggle with communicating his emotions, it’s also probable that he’s going to struggle to know if you see him as just a friend or if this is a romantic connection.

The more open you are about your feelings, the more you will encourage him to do the same. Dating a shy guy is absolutely nothing like dating anybody else in the dating world. 

It’s not fun to watch a person slowly crumble as they’re trying to figure out if your first date is actually a date.

Be plain about your feelings, wear your heart on your sleeve a little more than you normally would, and ask him how he feels in return. 

4. Appreciate the little things

appreciate the little things

Shy guys struggle to display affection in public, but this might happen in private too sometimes. 

Try to figure out his love language, and appreciate the small steps. The personal things. The things that he does to make you feel good when no one is looking. 

5. Don’t ever make him feel embarrassed for being shy

The number one tip to making things work with a shy guy is to never embarrass him or make a big deal of it when he’s acting shy.

He’s probably had a lifetime of people commenting on his character, and people encouraging him to be more confident. At the end of the day, he is who he is. You can try and help him of course, but don’t ever force him or make him feel attacked when actually, he’s just being himself.

6. Encourage socialization

But respect when he doesn’t want to go out. 

Encouraging socialization is good when dating a shy guy as it is important to spend time with other people, individually and as a couple. 

Often, shy guys want to socialize but are stopped as they can feel anxious. Going out as a couple might help a little with his social anxiety. 

6. Respect his boundaries

Shy guys can often be sensitive. Respect his boundaries and encourage him to be vocal when feeling sensitive or vulnerable. 

7. Encourage him to step out of his comfort zone 

You don’t want to change him, but you want to see him grow. When you care about somebody, you want to see them push themselves and reach their goals. 

If he has always planned on opening up a business but has been too scared, or if he’s always wanted to do something crazy like skydiving, then help him to achieve his goals! Be there for him, and encourage positivity

8. Don’t intimidate him

don't intimidate him

Sometimes, an excess of confidence can feel slightly overbearing. Do your best to not intimidate him, and maybe tone it down every now and again.

9. Understand the situation

Be perceptive of his shyness. He will often switch between good and bad days. Allow him to be confident when he’s feeling like it, but also step up and help him when he’s feeling shy. 


How do you flirt with a shy guy?

When flirting with a shy guy, you might have to put in extra work as he’s probably not the most perceptive when it comes to people flirting with him.

Sometimes, the best way to flirt is to literally tell him that you’re flirting with him, or by doing something very bold like giving him your number and asking him to call you.

How do you get a shy guy to make a move?

Getting a shy guy to make a move can be quite difficult. He will most likely avoid stepping out of his comfort zone, and wait for you to make the first move.

My advice, make the first move yourself, or simply tell him to make a move! There’s absolutely nothing wrong with asking him to ask you out on a date. Shy or not, you can usually tell when someone is into you.

How do you initiate intimacy with a shy guy?

Initiating intimacy can be difficult when this isn’t something that you’re used to.

My number one advice is to choose your moment carefully; especially in the early stages of dating. It might seem boring but wait until the movie is over, or wait until you’re in bed. Don’t take him by surprise.

Sometimes, shy guys need a little encouragement. There’s also absolutely nothing wrong with verbalizing and asking him directly.

How do you get a shy guy to open up?

Getting a shy guy to open up can take a lot of time and patience. You don’t want to overdo it by asking a million questions, so try and get to know him gradually.

He will open up in time. The more that you yourself are honest and open up, the more he’s likely to match your behavior.

How do you make a shy guy comfortable?

Naturally, your confidence should make him feel comfortable. Talk to him, have a normal conversation, ask him out on a date, take the lead. Make him feel as though dating isn’t a big deal, and make it very clear that you’re interested in getting to know him.

Figure out what his passions are, and ask him about them. If he loves animals, introduce him to your dog. If he loves to travel, ask him about his travel plans. Take baby steps, and listen to one another.


Remember, if he’s dating you, he’s probably pretty serious about you, so take the time to work on your relationship for the better.

Your relationship will naturally be rawer and more vocal than others as you will need to communicate to get past certain barriers. The benefit of dating a shy guy is that you clearly have something special together. 

Never try to change him, the same way you wouldn’t want somebody to change you, and always remember why you were attracted to him in the first place. 

It’s perfectly normal to have days where you get frustrated with him or his behavior, like in any healthy relationship. But once you learn to understand each other, you will be able to vocalize your emotions successfully and work through any problems that you might face together.

If you have any tips or stories from dating a shy guy, feel free to comment to help other women in need of advice! And as always, share this with a friend in need.

Utilize this tool to verify if he's truly who he claims to be
Whether you're married or just started dating someone, infidelity rates have risen by over 40% in the past 20 years, so your concerns are justified.

Do you want to find out if he's texting other women behind your back? Or if he has an active Tinder or dating profile? Or even worse, if he has a criminal record or is cheating on you?

This tool can help by uncovering hidden social media and dating profiles, photos, criminal records, and much more, potentially putting your doubts to rest.


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