15 Tips for Dating a Shy Guy

Thanks to anime and coming-of-age movies, people love to think they want to find a quiet, shy guy to date. What they don’t understand are the unique challenges of dating someone who is naturally bashful.

These types of men make fantastic partners, but getting them to open up and be comfortable with you can be a challenge.

Today, we are going to look at the 15 best tips for building a loving, trusting relationship with your shy partner.

1. Make it Clear You are Interested in Him

Before you can date a shy guy, you have to let him know you are interested. You may think your subtle flirting is working on him, but think again!

It’s not that he doesn’t recognize your behavior as flirty, he is simply too shy to act on it. In his mind, all he can think about is being wrong and you turning him down!

So, if you are truly interested in him, lay it on thick. In fact, the best option is to just tell him straight up, “I think you are cute and that we should go out sometime.”

2. Learn His Language

Once you are communicating with your shy love interest, you can begin learning how he communicates. Maybe he is too shy to shout his desire for you from the rooftops but he may be more open to writing you a long text message about his feelings.

Take the time to see how he is comfortable communicating and try to meet him at least halfway.

3. Give Him Genuine Compliments

Some men are shy as a symptom of having no self-confidence. It isn’t your job to fix all his issues, but giving him genuine compliments and showing him his worth is a great way to be a loving partner. Over time, he may begin to blossom.

4. Find Some Common Ground

When shy guys are out of their element, they tend to shut down. To remedy this, try finding places to go that you both enjoy. Are you both fans of comic books? Consider asking him to accompany you to a comic store or even a ComicCon-style event. These types of suggestions not only help him to feel comfortable but show him that you know his interests.

5. Don’t Tease Him for Being Shy

The worst thing you can do to a shy person is tease them for being shy. It makes them hyper-aware of their own shortcomings, which results in them being more closed off.

6. Don’t Be Afraid to Make the First Move

If you feel like the moment is right for a first move, take it. This removes the pressure on him to overcome his shyness and do it himself! Once you have broken the barrier of physical intimacy, he will likely be more comfortable making moves in the future.

7. Get Him Talking About His Interests

If you want to get a shy guy talking, bring up some of his interests. Many shy people tend to have hobbies they are passionate about, but don’t often get to discuss.

8. Try Not to Overshadow Him All The Time

Dating a shy guy doesn’t mean dulling your own shine, but remember that it can be easy to feel like you are in the shadows when your partner talks over you or ignores your needs. Take the time to listen to him and include him in conversations.

9. Don’t Pressure Him

If you treat a shy guy well, he will eventually open up to you, but don’t pressure him to get there on your terms. It can take time for shy people to feel comfortable with a new person.

10. Be An Open Book for Him

Your partner may be too shy to ask you questions about your past, family, personality, etc. Try being an open book for him so that he can truly learn who you are and not stand in his own way of getting to know you.

11. Give Him Clear Expectations for Your Relationship

While it is important to understand your shy partner, you shouldn’t have to lower your standards for him. Let him know exactly what you expect out of a relationship. That may be someone who goes with you to work events or is open to taking pictures for Christmas cards. If he knows what you are wanting and doesn’t think he can manage, it gives him the opportunity to walk away before anyone gets hurt.

12. Learn to Notice When He is Flirting With You

Sometimes shy guys aren’t the best flirters. They tend to approach flirting with subtlety and through kind actions.

  • Does he try to be where you are at parties or other social events?
  • Does he catch your eye from across the room just to smile and look away?
  • Does he like every. single. post. on your social media?

These are all ways that shy people flirt. It is all about getting your attention and being near you in the least scary way possible.

13. Compromise On the Types of Dates You Have

Dating a shy person (especially if you are an extrovert) is a game of making compromises. If you want him to step outside of his comfort zone for you and go to parties or clubs, you need to return the favor by having low-key dates he will enjoy.

14. Don’t Take His Shyness Personally

When you are used to being constantly praised or openly flirted with, a shy guy can come across as uninterested. Try not to take his shyness personally. Over time, he will become more comfortable with openly fawning over you.

15. Don’t Break His Trust

If you want a shy guy to learn it is safe to open up to you, you have to respect his privacy. If you run around and share all his secrets with your friends, you are only showing him that he was right to not tell you anything.

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Author: Matt Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.