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Dating a shy guy: 27 tips you need to know

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Dating a shy guy isn’t easy.

If you want to make it work, you need to know how he works.

Here’s a guide to decode your shy guy.

Dating a shy guy: 27 tips you need to know

1) He works a bit differently

Every guy has moments of shyness when he’s around a girl he likes.

The difference with a shy guy, is that these moments of being withdrawn, shy and quiet don’t end.

Just because you break the ice or you two end up going out, doesn’t mean he’s going to “warm up” or break out of his shy behavior.

Being a shy guy isn’t a phase, it’s a real personality type.

And if he’s displaying a lot of shy behavior, it’s important for you to not take it personally.

These include things like him:

  • Not speaking much
  • Avoiding eye contact
  • Having trouble expressing emotions
  • And being shy to meet your friends and family

Understanding that a shy guy works differently is key to having a healthy relationship with him.

But one way in which he works the same as other guys is the following tip:

2) Make him feel like a hero

If you’re having a hard time understanding your shy boyfriend, there’s a solution.

The solution is to tap into his deep biological drives.

There’s actually a psychological term for what I’m talking about here. It’s called the ‘hero instinct’.

This concept is generating a lot of buzz at the moment as a way to explain what really drives men in relationships.

I know it might all seem kind of silly. In this day and age, women don’t need someone to rescue them. They don’t need a ‘hero’ in their lives.

But this misses the point about what the hero instinct is all about.

The hero instinct is an instinctive need that men have to step up to the plate for the woman in their lives. This is deeply rooted in male biology.

When a man genuinely feels like your everyday hero, he’ll become more loving, attentive, and committed to being in a long-term relationship with you.

But how do you trigger this instinct in him?

The trick is to make him feel like a hero in an authentic way. And there are things you can say and messages you can send to trigger this natural biological instinct.

If you want some help doing this, check out James Bauer’s excellent free video here.

He tells you everything you need to know about the hero instinct, including exactly how to trigger it in your man.

I don’t often recommend videos or buy into popular new concepts in psychology, but the hero instinct is one of the most fascinating concepts I’ve come across.

Here’s a link to his unique video again.

3) You probably have to make the first move

There’s still quite a bit of culture out there which expects a guy to make the first move.

The truth is that from my experience it’s often the woman who makes the first move. She just tends to do so more subtly, with prolonged eye contact, an inviting smile or a flirtatious question.

But when it comes to dating a shy guy, you have to turn this up another notch even further.

He may be showing no apparent signs of interest and you as a woman have to still make that executive decision to ask him out.

It can be hard to build up a huge rapport before that because shy guys don’t usually like chatting it up.

So you may have to go with your gut on this one.

If you’re feeling interested and you think he might be too, then keep in mind that it might well be up to you to make the first move.

4) Notice his subtler signs of interest

Shy guys show interest differently. When it comes to making the first move, that’s one thing, but what about knowing if he’s even into you?

The best way to assess that is to be attuned to his subtler signs of interest.

Later on I will talk more about body language, which is one important aspect of learning to understand and relate to your shy guy.

In addition, you want to be attuned to:

  • His ways of expressing himself non-verbally
  • His habits and ways of responding to you
  • His mode of showing emotion and excitement with his expression and facial mannerisms

By getting to know the subtler cues and signs that he’s interested, you can ensure that you make a move at the right time.

5) Don’t expect him to fully open up

Shy guys are a bit of an enigma, because there seems to be a part of themselves and their emotions that remains permanently closed off.

But the more pressure you exert, the bigger the barriers get.

Remember that it’s his choice how much he opens up or not, and that you can’t force it.

At the same time, showing curiosity and asking him questions is a good thing as long as you’re perceptive about his reaction.

If he actively avoids answering anything or talking, then move on and try to focus on something else.

Maybe an activity you can do together…

Or talking about an interest you know he has, rather than his own life…

The less social expectations you have on a shy guy, the more opportunity for him to find a small comfort zone of his own and begin opening up voluntarily at his own pace.

6) Find out what you share in common

Dating a shy guy can be a lot of fun if you go about it the right way.

The key is to focus on what you have in common, rather than on the communication barrier that you may feel with him sometimes when you’re together.

Finding out what you share in common is just a matter of curiosity and attention to detail.

If you find most of his interests strange, try to find one activity you can share joy and couple time doing.

Maybe it’s baking pizza together…

Going ice skating…

Listening to an epic fantasy audiobook…

Or nerding out while playing vintage arcade games…

Whatever your shared passion is, try to find it and do it together!

7) Give yourself time to adjust

If you’re used to dating guys who are more on the extroverted side, then dating a shy guy can be a bit of an adjustment.

Give yourself time to adjust and don’t push yourself.

Getting familiar with a guy who moves a bit more slowly and doesn’t speak as much can be tricky.

It can take time – and patience – to work through misunderstandings and slow periods with him.

You may even go a fair while wondering if he’s actually into you or just playing the field and acting shy for leverage.

Give it time, the truth will win out in the end.

8) Keep questions open-ended

Open-ended questions are a girl’s best friend when it comes to dating a shy guy.

By asking questions that give him plenty of space to say what he wants, or keep his words to a minimum, you’re taking the pressure off and letting the relationship grow naturally.

Classic open-ended questions can be things like:

  • How was your childhood?
  • Do you have some things which you really hate?
  • What do you like most about living in this area?
  • What are your plans for the future?

If he goes with “it was alright,” “I hate traffic jams” and “it’s OK here,” then don’t push it.

If he wants to open up more, then great.

The point is that by asking questions like this you can give him the chance to be as open or closed as he wants.

9) Let silence become your romantic glue

With a shy guy, silence is going to be pretty common.

But if it seems awkward to you at first, it doesn’t have to be. Let silence stick around for a bit and make eye contact or touch.

Then let silence stay around even longer as you spend time together or bond in various ways.

The energy between you can be more powerful than words.

Connected silence can become the romantic glue that keeps your relationship together. 

10) Keep his secrets

If and when a shy guy does open up, he needs to know that the vault remains sealed.

If he shares personal information with you or allows himself to be vulnerable, you need to let him be confident you’re not going to share that around.

The best way is to keep his secrets and show him that you intend to do so going forward.

Sometimes one of the reasons men are shy is as a result of being burned in the past.

So unless he tells you there’s a body in his closet, due your best to keep the private things he tells you in confidence.

11) Texting can be your love language

Another one of the best tips you can learn when it comes to dating a shy guy is to master texting.

The great thing about texting is that you can be really shy and still be an amazing texter.

You might be shocked at how flirtatious and open a shy guy gets when he’s twiddling his thumbs on his touchscreen.

The emojis start flying and his heart opens up to you.

That’s why texting is often perfect as a love language if one partner is on the shy side.

Give it a try.

12) He’ll take awhile to open up to your friends

Dating a shy guy means that you need to take it slow on introducing him to family and friends.

He may end up loving them, but if you invite him to a surprise party with 30 people he’s probably going to shut down and get serious social anxiety.

Let your shy guy move slow.

Introduce him to people at a slow trickle, one by one or in small groups.

He’ll adjust much better that way and be grateful to you for respecting his boundaries as well.

13) Be ready for him to make physical moves more slowly

Guys can be shy in two ways: socially and sexually. Often, shy guys are on the timid side in both categories.

For this reason, you have to be prepared to take the lead a little bit with your shy boyfriend.

If he’s shy about making a move physically, guide him to it.

If he hesitates a lot or doesn’t seem eager to get physically intimate, let it happen naturally.

14) Learn his body language

As I wrote earlier, one of the key things to learn with a shy guy is the nonverbal cues that show what he’s feeling.

Nothing is more important than body language.

Common body language cues including when he’s trying to get close to you, orienting his feet towards you, playing with his hair and making intense eye contact.

Because he’s a shy guy, he will often avert his gaze quickly when you catch him staring.

But don’t be fooled: he’s into you.

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15) Keep your foot off the pedal

Shy guys can be really hard to read.

That’s why it’s vital to trust your own gut instinct and know how fast to move.

Generally speaking, you should keep your foot off the pedal and wait for a thumbs up from him.

If he isn’t giving you that, at least wait for a smile!

16) Give him the chance to be a listener

If you like talking, then having a shy boyfriend can actually be a good thing.

One of the best aspects of shy men is that they’re often really attentive listeners.

His advice may be short and sweet, but it will tend to be really insightful.

Plus, having a partner you can open up to and spill your guts to can really just be a blessing in and of itself.

17) Connect with his family and friends

Even the most timid guy out there has family and friends who care about him.

Do your best to connect with them and let them know that you’re in his life.

He’ll really appreciate you making that effort.

Furthermore, it’s not always easy for a shy guy to reach out and make introductions, because he may feel awkward about it.

Taking the lead on that score can go a long way to gaining his trust and admiration.

18) Improve yourself first

One of the worst things you can do with a shy guy is push too hard.

Even if he’s very attracted to you, if you come after him too openly and strongly, he may retract back from you and run away.

The best thing to do if you’re unsure where you stand and are afraid to wreck your connection is to take a pause.

I know that you probably just want him to explain himself and tell you what he wants you to do right now to make him feel comfortable…

But when it comes to relationships, you might be surprised to hear that there’s one very important connection you’ve probably been overlooking:

The relationship you have with yourself.

I learnt about this from the shaman Rudá Iandê. In his incredible, free video on cultivating healthy relationships, he gives you the tools to plant yourself at the center of your world.

And once you start doing that, there’s no telling how much happiness and fulfillment you can find within yourself and with your relationships.

So what makes Rudá’s advice so life-changing?

Well, he uses techniques derived from ancient shamanic teachings, but he puts his own modern-day twist on them. He may be a shaman, but he’s experienced the same problems in love as you and I have.

And using this combination, he’s identified the areas where most of us go wrong in our relationships.

So if you’re tired of your relationships never working out, of feeling undervalued, unappreciated, or unloved, this free video will give you some amazing techniques to change your love life around.

Make the change today and cultivate the love and respect you know you deserve.

Click here to watch the free video.

19) Be ready for some surprises

Shy guys don’t usually talk much, but when they do, they often drop bombshells.

Don’t act overly surprised if he says something about himself you never knew, even after months or years of being together.

On the other hand, never let him use his shyness for not being honest or hiding something important from you.

Those are two totally different things!

20) Let him have his down time

Shy guys need their fair share of down time.

They are introverts and often they are also high sensitive people (HSPs).

For this reason, they need quite a bit of time to recharge, particularly after busy social situations and encounters.

As Ratika Pai writes:

“Shy guys often need to retract into their shells from time to time. During such a phase, try to understand him and give him time to himself.”

21) Separate fights from shyness

Fighting with a shy guy is kind of passive aggressive in most cases.

If you’re dating a shy guy then you know that it can be hard to sort of when he’s mad at you or when he’s just having his down time which I spoke about in point 24.

Make sure you get clear on what is what.

If he’s not explaining it well, maybe his friends and those close to him can help you figure out how to separate the two.

22) Get clear on whether he has more serious issues than shyness

There’s nothing wrong with being shy, obviously.

But there are cases where it crosses the line into something else entirely.

Sometimes extreme shyness can actually just be the exterior of someone who’s battling serious issues with anxiety and depression.

Make sure to let him know that he can always open up to you, and be on the lookout if he starts having a lot of the symptoms of serious mental illness.

23) Know when he’s rejecting you for real

One of the things with a shy guy that’s hardest to deal with is the feeling that he’s shutting you out when he’s actually not doing that.

For this reason, it can be easy to jump the gun and think he’s turning you down or wants to break up, even when he doesn’t.

But let’s face it:

Sometimes he really does want to break up.

And if he’s not answering any messages or directly tells you it’s over, then you have to realize that he definitely isn’t into it.

It takes a lot for a shy guy to step out of his comfort zone and reject someone, so if he did that with you then chances are he really means it.

24) Getting a shy guy back

Let’s face it:

Dating a shy guy isn’t always easy.

If you were dating a shy guy but it didn’t work out, take cheer.

There’s still hope, even if you’ve already broken up.

The key is to appeal to his inner desires without scaring him away.

And there’s a simple way to do so.

In fact, one of the easiest ways you can win your ex boyfriend back is by simply sending him the right text messages.

Yes, it’s entirely possible to effectively “text your ex back”. Even if you thought that it was impossible to ever rekindle any sort of romance with him.

There are literally dozens of text messages you can send your guy that will compel him to keep texting you. And ultimately lead you guys back together.

But you need to have a plan of attack and send these messages right when he’s most likely to take them seriously. Only then do you induce a “fear of loss” within him.

Pro tip:

Try this “Jealousy” text.

— “I think it was a great idea that we decided to start dating other people. I do just want to be friends right now!” —

By saying this, you’re telling him that you’re actually dating other people right now… which will in turn make him jealous.

This is a good thing.

You’re communicating to him that you’re actually wanted by other guys. Men are attracted to women that are wanted by other guys. By saying that you’re dating around already, you’re pretty much saying that “it’s your loss, mister!”

After sending this text he’ll begin to feel attraction for you again, and that “fear of loss” will be triggered.

I learned about this text from Brad Browning, who has helped thousands of women get their ex back. He goes by the moniker of “the relationship geek”, for good reason.

In this free video, he’ll show you exactly what you can do to make your ex boyfriend want you again.

No matter what your situation is — or how badly you’ve messed up since the two of you broke up — he’ll give you a number of useful tips that you can apply immediately.

Here’s a link to his free video again. If you really want your ex boyfriend back, this video will be incredibly helpful.

25) Let his friends and family help guide you

Your best potential assets when it comes to dating a shy guy are his friends and family.

They know him better than anyone, and they can give you advice that’s pure gold.

They can read you in on his past, his pet peeves and the way that he processes experiences.

It’s sort of like getting a cheat sheet for a big test, except in this case the “test” is your boyfriend’s heart.

26) Be his go-to girl

Shy guys don’t tend to have huge inner circles.

When he knows he can open up to you and trust you, that will build a lot of intimacy and closeness in your relationship.

Be his go-to girl who he knows that he can open up to and be himself with.

He’ll appreciate that a lot and begin to see that you’re not expecting anything else from him other than to be himself.

27) Don’t take it personally

One of the biggest mistake some women make with shy guys is that they mistake his shyness as him being upset at you or not into you.

As Julia Pugachevsky puts it about her own experience dating a shy guy:

“This one will drive you nuts because you know when *you* get quiet, it’s 100 percent intentional passive aggressiveness designed to make the other person slowly crumble.

Not to the shy guy.

He truly, genuinely is just floating in his own world for a hot second.”

Don’t shy away…

If you’re dating a shy guy, or want to date a shy guy, take note:

Don’t shy away.

Don’t take his shyness personally, and have patience.

I know it’s not easy, but you can take confidence from the fact that many have gone before you and built successful relationships with shy men in the past.


By now you should have a good idea of why dating a shy guy can be so hard to get right.

So what can you do to resolve this?

Well, I mentioned the unique concept of the hero instinct earlier. It’s revolutionized the way I understand how men work in relationships.

You see, when you trigger a man’s hero instinct, all those emotional walls come down. He feels better in himself and he’ll naturally begin to associate those good feelings with you.

And it’s all down to knowing how to trigger these innate drivers that motivate men to love, commit, and protect.

So if you’re ready to take your relationship to that level and get out of the traps of the anxious-avoidant pattern, be sure to check out James Bauer’s incredible advice.

Click here to watch his excellent free video.

How this one revelation changed my love life

It’s Justin Brown here, the co-founder of Ideapod, and I have something to confess…

I used to believe I needed to be successful before I deserved to find someone who could love me.

I used to believe there was a “perfect person” out there and I just had to find them.

I used to believe I would finally be happy once I found “the one”.

What I now know is that these limiting beliefs were stopping me from building deep and intimate relationships with the people I was meeting. I was chasing an illusion that was leading me to loneliness.

If you want to change anything in your life, one of the most effective ways is to change your beliefs.

Unfortunately, it’s not an easy thing to do.

I’m lucky to have worked directly with the shaman Rudá Iandê in changing my beliefs about love. Doing so has changed my life forever.

Now, Rudá’s teachings can change your life, too.

As the co-founder of Ideapod, I’m in a unique position to be able to bring Rudá’s teachings to our global community.

We do this by promoting his masterclasses.

One of the most powerful masterclasses he has is the love and intimacy masterclass. In this class, Rudá breaks down his key lessons on cultivating healthy and nurturing relationships in your life.

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Best wishes,
Justin Brown, Ideapod Founder

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