How To Date A Shy Guy

He’s not the chattiest. He’s not the most confident. He’s not even the hottest. But there’s something endearing about him, and you’d like to know more.

He’s the shy guy. The guy you’ve noticed at work, university, or through a friend, who just seems sweeter every time you talk to him.

Depositphotos_40728389_l-2015OptimisedThere’s good reasons a shy guy might make a great partner. His quietness could reflect his thoughtful nature, showcasing a man, who is caring and considerate. His introverted communication style means he’s unlikely to seek validation from others as an extrovert would. His shyness could even reflect a commitment mindset – a man with less interest in playing the field.

Shyness, however, brings challenges, especially in dating. Not just for him either; it goes for his would-be date, too. Shy guys have potential as great partners, but courtship and dating shy men has its challenges, something you must be aware of if snagging a shy guy is your plan.

So how do you go about dating a shy guy?

1. Make sure he is a shy guy.

The biggest mistake I see women make trying to date a shy guy is confusing him with a normal guy who’s just not interested.

This is important, because the way you get a shy guy is the same way you look desperate to a normal guy.

“The biggest mistake I see women make trying to date a shy guy is confusing him with a normal guy who’s just not interested.”

Courting a shy guy is about you doing a lot of the work for him. If you pull that on a disinterested guy, you’ll probably get used for sex. It’s important to tell them apart.

Here’s some signals to help you:

Shy guy:

Doesn’t or rarely starts conversation with you, but seems enthusiastic when you start them.

Stumbles on his words or seems a little awkward around you.

Doesn’t seem to have a sexual bone in his body, the last guy you can imagine hassling you for sex.

His friends tell you he’s shy, but interested.

Nice to virtually everyone who talks to him.

Normal, disinterested guy:

Doesn’t seem enthusiastic when you start conversations with him.

Has no problem talking to you – just seems bored or disinterested when he does.

Has hit you up for sex – or – you could easily imagine him doing so.

His friends or others have mentioned nothing.

He’s only nice to people who talk to him he likes – others get the cold shoulder.


2. You will have to make most moves.

Here’s the big difference in dating a shy guy. In a normal dating situation, the man will generally do most of the work moving things forward. He’ll ask you out, he’ll lean in and kiss you, and at some point, he’ll probably try to sleep with you.

Even if you do a couple of these things yourself, most Depositphotos_14757815_l-2015Optimisedwomen are happy handing it back to the guy to do the rest. Making all the moves on a man just leaves them feeling desperate.

Besides, men usually want to work to win you over, too.

With a truly shy guy, this no longer applies.

If dating a shy guy is your aim, you’ll have to be OK playing the traditional ‘masculine’ role during dating. You’ll have to be cool with asking him out. You’ll probably have to kiss him. You’ll likely have to lead him to the bedroom, and depending on the guy, may have to lead the process once you’ve got him there!

Sometimes, the shy guy will take over, and his confidence in various areas will grow as he gets more comfortable with you. However, if you like a guy who can throw you around confidently the first time you’re together, a true shy guy may not be for you.

3. See how you feel and how he responds.

In for a penny isn’t in for a pound. Perhaps you’re willing to make one move on him before deciding you’ve had enough. Maybe you don’t mind making the first few moves, but decide that, if he doesn’t do it for you sexually, you pull the plug. Or maybe, you have no problem getting into a relationship with a shy guy, but long-term need to see his masculine side come through for things to last.

There are numerous permutations, and you have to decide where your line is – i.e. how much shyness are you willing to tolerate before you begin to lose attraction. Some women are unfazed; others want a man who can lead.


Common questions I get relating to this advice:

What if he never comes out of his shell?

That’s going to come down to a personal decision for you. You can’t ‘save’ him from his shyness, only help him work on it if it’s something he wants. If you don’t mind playing more of the ‘alpha’ role in your relationship, it may not matter at all.

What if he’s showing a lot of signs of shyness, but still wants to have sex?

This situation should usually set off some alarm bells. Shy guys are congruent – their shyness reflects across their life. Be wary of being used if he is hassling you for sex.

His friends say he’s interested, but I’m getting uncomfortable making all these moves. I feel like I’m desperate. What should I do?

As long as the friends are close to him, they are a reliable source. There is a ‘bro code’, where guys know not to push it if you’re not the right girl.

There’s various things you can do to help point him in the right direction. Wait until the end of a great date and say to him, “I had so much fun tonight. Your turn to call me next time, and I’d love to do it again!” Alternatively, you could tell his friends that you like him too, but you’re expecting him to put in some effort for things to go ahead. There’s all sorts of ways to help him with green lights and guide him (hopefully) down the path.

Still, if you’re getting uncomfortable having to do all this or making all the moves yourself, dating a shy guy may not be for you.

“…dating a shy guy means a different dynamic, one in which you will be playing more of a leadership role. Ask yourself if you’re ok with that.”

In summary, dating a shy guy means a different dynamic, one in which you will be playing more of a leadership role. Ask yourself if you’re ok with that.

If you decide you are, double check he is a shy guy (not just a disinterested guy), trust your instincts, then go after him! While they may be a little harder to court, a good relationship with a quality shy guy can be one of the most rewarding, fulfilling, and loving experiences out there.

Interested in knowing more about how to date particular types of men? Click the link here to receive my FREE eBook on “The 10 Male Dating Personalities That Can Lead to Heartbreak.” It discusses many of the most commonly found male dating personalities, so you know what they are and exactly how to handle them.




Meet Mark Rosenfeld

The Dating & Relationship Breakthrough Coach For Women

For the past 7 years, I’ve coached hundreds of women just like you. Whether you are working through a breakup, looking for your life partner or pursuing a better relationship with yourself — I have the tools and strategies you need to deepen your connections, increase your fulfillment and sustain meaningful relationships.

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