15 Proven Ways To Date A Shy Guy Successfully

By David Small •  Updated: 02/13/18 •  11 min read

Are you looking for tips to help you to date a shy guy? Are you waiting for the man of your dreams to approach you and initiate a date? You are living in the past!

If the man is a shy guy, you might have to wait for years to enjoy the companionship that you crave and the great dating experience that you deserve.

Note from the onset that men might not be shy with their friends, but may develop cold feet when approaching girls.

How To Date A Shy Guy Successfully

Photo by Bruce Mars

This Post May Contain Affiliate Links. Please Read My  Disclosure For More Info.

If this sounds like the story of your life, there is still some help for you. Discover 15 tips that have been tried and tested by girls dating shy guys.

These tricks can work wonders when practiced carefully and naturally. Otherwise, you could scare the guy and stop him in his tracks, effectively escaping an amazing date and the love of your dreams.

In this article 15 Proven Ways To Date A Shy Guy Successfully we share with you way to assist you in dating shy guy successfully.

Related Articles


Tip Number 1: It’s never that serious!

Are you angry, disgusted and embarrassed about the shyness of your boyfriend? You are increasing the problem instead of eradicating it. This is according to Jessica Booth, the writer of the blog post titled “10 Tips on how to Date a Shy Guy” appearing on the website gurl.com. Jessica states that your man will lack self-esteem if you ridicule or mock his shyness.

Note that you met him a shy person and you cannot change this fact in just a few days. If his parents did not succeed at it while he was growing up, what makes you think that you will be successful? Avoid taking it personally when on a date and instead, appreciate him the way he is. Soon afterward, he will open up to you because you truly understand him.

Tip Number 2: Grab the bull by its horns

Do you think that your waiting for him to be an extrovert is taking too long? It is time to grab the bull by its horns. In so doing, avoid confronting him as this might negatively dent his ego. Instead, ask him about it and let him know that you are willing to do anything to help. He might not come out of his cocoon as fast as you imagine, but do not relent.

Redbookmag.com outlines 15 things that man thinks are absolutely romantic. One of these is the touching game towards your date. The website advice you to touch, flirt and pat your shy guy in ways that encourage him to do the same. It, however, cautions you from being an outright flirt as this may send the wrong message. Observe his reaction to your touches and increase the pace.

Shy Guy

Photo by Spencer Selover

Tip Number 3: Talk on Social Media

What if the both of you are shy? Your date is likely to be boring and somewhat uncomfortable. If you are a shy girl and the man of your dreams is shy as well, take it to social media. This is according to the blog lovedevani.com. This tip is discussed in the post titled “17 Ways on How to Talk to a Shy Guy You like When You’re Shy”.

When the two of you are far apart, you have the space to say things that you would not have said when you are together. Take advantage of this and send kinky messages and images. There should be no limit to the content and intensity of communication on social media. Ask all the right questions and ensure you get answers to these. Reply to his questions conclusively.

Tip Number 4: Compliment Him

Allwomenstalk.com is a leading resource for women. If your guy is timid and not ready to date, find help from the column titled 15 tips for dating a shy guy. One of such advice is to compliment him when he does or says something that is really great and manly. An example is when he buys you flowers or takes you for a lunch date.

Showing your praise, commendation, and appreciation is a great way of making your man aware of his strengths. He will surely do many other good deeds in an effort to make you happy. As you continue to date, he will find his self-confidence all over again for the benefit of the both of you.

Tip Number 5: Initiate sexting


Photo by Bruce Mars 

Nobody wants to date a shy guy for years without shifting to a higher gear. If your boyfriend is extremely shy, he may never initiate the topic of sex leave alone the act itself. The result is an acrimonious union that lacks the vigor and fun that sex brings. You can start sexting your shy guy and get him to open up on the often feared subject.

Love Panky is an online guide for people in the dating game. One of its most read blogs is titled How to Get a Shy Guy to Like You and Ask You Out. According to the blog, sexting is a sure way of making your man comfortable and plant the seed of desire in his heart. Prepare him mentally so he can’t wait to get laid when you meet next.

Tip Number 6: Ask for his help

Are you the brave and bold woman who can do anything by herself? Chances are that you are scaring men away from you. Men are naturally created to find attraction in women that they can help. This is according to the blog slism.com. It emphasizes this point in one of its most-read blog post titled “How to Talk to a Shy Guy with 9 Ways to Get Him Talking to You”.

Let him find something that he can do to contribute to the safety and comfort of your life. Ask him to fix broken items such as the computer or coffee table. Do not ask him to wash your clothes or other feminine chores that will actually hurt his ego. When men know that they can assist you with a task, they become more confident, bold and assertive.

Tip Number 7: Respect his boundaries

The fact that you are trying to get a shy guy to date you does not mean invading his space. Even married couples need personal spaces and lone times. The author of the post 12 Tips to Get a Shy Guy to Like You on Datetricks.com advice to let him work, study and play away from you. As much as you have made your feelings known to him, give him space and time so that he actually misses you.

Avoid the temptation to spend all the time with him. He sometimes needs to be with his drinking buddies. If he feels that you are nagging or redundant, he will bolt away as fast as his thin legs can run. Simply put, learn how to strike a balance between spending time with him and letting him be.

Tip Number 8: Learn from his body language


Photo by Lukas Hartmann on pexels.com

Actions speak louder than words. This age-old saying perhaps applies to the dating game more than it does elsewhere. A shy man may never say that he cares for you, but his body language speaks volumes. Does he look at you in a suggestive way? That sign is enough that he cares for you.

A man will look at you when you are not looking at him to feed his eyes. If he looks away when you face him, there is something he is interested in seeing. If he shakes or makes incoherent mumbles with his hands or fingers, this is a clear sign. Does he behave differently with you than with other girls, this is the clearest sign yet that he is eyeing you. Grab the chance while it lasts.

Tip Number 9: Let him know your feelings

Have you told that good looking guy who has been a close acquaintance that you care for him? If not, how else do you expect him to know how you feel about him? Many people in the world fail to date the people they admire because they are coy about letting their feelings known. The fear of rejection is real in dating. Banish yours today and get the man you deserve.

The Datemix.com is a resourceful online tool for people in the dating game. One of its hard-hitting posts is called “Dating Advice for Shy People”. This resource advises you to communicate your feelings effectively to the other party. Find a reasonable date and time to lay bare your feelings. Ensure that the person understands exactly how you feel, so there are no doubts.

Tip Number 10: Start with simple things

Cyrus Thompson is the author of Love and Dating for Shy People. This is a bold guide for people who are naturally introverted to find love and companionship. It states that you should keep the pace slow as you start to avoid scaring the other person. When you create a great first impression, you can rest assured that the date will go on for many months or years.

Holding the hands of your prospective date is a simple yet effective approach. He understands that you treat him more than just a friend. Take the game forward with a simple hug and then a kiss on the cheeks. This prepares him for the date without freaking out the poor shy man. You might be pleasantly surprised when he shifts the tempo upwards.

Tip Number 11: Initiate love and sex

How To Date A Shy Guy Successfully

M. Harrison is the author of The Book of Shy Guy Body Language and Shy Girl Body Language”. It discusses non-verbal cues that you could use to initiate the process of lovemaking. Harrison is an expert in sign language and non-verbal communication. He helps you pass covert messages to your shy guy during the dating game.

The book emphasizes the point that 93% of all communication is done through non-verbal cues. When you utilize them properly, you will date your shy guy successfully. This book also helps you pinpoint and understand non-verbal moves that your shy guy makes that could mean a lot for the strength and comfort of your relationship.

Tip Number 12: Watch movies together

Learn, share and obtain experiences from what other people go through in their lives. One of the richest resources for you today is movies, and there are thousands of them. Do you want to download a guide from YouTube or watch a dating game on Netflix? There are so many sources of dating knowledge that you cannot afford to procrastinate.

Christopher Gray is the author of From Shy to Social: The Shy Man’s Guide to Personal & Dating Success”. Christopher agrees that an hour of watching a movie together brings out find memories in date couples. Your shy guy will look forward to meeting you again for another episode of a mutually enjoyable movie.

Tip Number 13: Invite him to your hood on A Date

Do you always spend time at your guy’s house? Why not switch to your house? Gregg Michaelsen, the author of “Be Quiet and Date Me” believes that switching places can make your shy guy bold and assertive.

Let him see what kind of girl you are by simply having lunch in your house. Inviting him in your life is a sure way to say that you trust him with your things. As he becomes comfortable around your house, his self-confidence increases.

Tip Number 14: Talk to his friends


Photo by Bruce Mars on pexels.com

Do you have mutual friends? Chances are that he will treat you differently from the way he treats everyone else. Make the most use of this window of opportunity to know things about him that he would not ordinarily tell you.

“Single, Shy and Looking for Love” is a book authored by Shannon Kolakowski. Shannon believes that his friends could reveal a secret behind his shyness. Expound on this secret and find a solution for the man you love.

Tip Number 15: Engage in mutual hobbies

Did you just realize that your shy guy loves skydiving just as much as you do? Set your date to the skies and engage in an activity that the both of you enjoy. Chances are that he will lose himself, including his shyness and reveal his true self in the thick of the hobby.

This trick is highlighted by Lane Moore in the Cosmopolitan.com.  In her blog called “11 Problems, only Women Dating Shy Guys Understand”. Lane is the view that mutual hobbies bring people closer to one another. This effectively cements a bond of love, understanding, and fulfillment.

In conclusion;

Give that shy guy a chance today!Your love life will forever thank you.


David Small

is the founder and editor of relationshiptips4u. He is a dating, marriage & relationship coach, speaker, and author. Learn more about him here and connect with him on Twitter, Facebook, and LinkedIn.

Keep Reading

error: Content is protected !!