6 Essential dating tips for shy guys (from a former shy guy)

Shy guys will learn skills needed to deal with shyness, which girls to ask out, how to ask girls out, how to deal with rejection, how to have a successful first date and which date activity to choose.

1. Dealing with shyness

Causes of Shyness:
Shyness is often caused by fear of new people and new situations. Another cause of shyness is due to low self-esteem. Another big cause of shyness is due to fear of people’s hidden thoughts and judgments about you. While there are many reasons for shyness these three are really big factors. The common aspect of these causes is that they are all self-imposed limitations.

Effects of Shyness:
Shyness often holds people back from doing things that they like to do including meeting new people, going to new places, and doing new things. Shyness usually causes people to minimize emotional risks in their life. Shyness, especially in the extreme, can lead to anxiety, social isolation, and depression. If your shyness is strong, you ought to seek professional counseling.

Skills to Develop in overcoming shyness:

Accepting change
Shy people usually fear change and so it is very important to learn to accept change. Shy people need to learn to accept the risk of things going in ways they didn’t expect. They need to learn to be more spontaneous and flexible. Push yourself to try one new experience every day, or talk to one stranger. Over time you will become more comfortable with change.

Overcoming fear with humor
Shy people are often controlled by their fears, but one of the ways they can overcome their fears is through humor. Humor allows you to make light of difficult situations and that is an often a very strong way to bond with other people. In fact, laughing will help reduce your fear by channeling your fear-based energy into something socially positive. Every stand-up comedian is inwardly scared to death of failure.

Shifting focus from protecting self to compassion for others
The obvious reason people are shy is that they are overly focused on themselves and how other people may judge them. So the way to overcome shyness is by being less concerned with yourself and more concerned for others. Compassion and altruism are very effective ways of overcoming shyness. Become an active listener to others and learn to share their concerns. This is a great way to become more popular without having to be a good conversationalist.

Being assertive without being controlling
It is very difficult for shy people to be assertive except when they lose control and have excessive anger. But shy people can learn to be assertive, to stand up for themselves, and ask for what they want without losing control and becoming angry. Learning to experience new situations without trying to control the situation is a very important skill to learn for shy people. If you feel a loss of control, take a deep breath and count to five silently. Then kill everyone in the room. (Just kidding.) Then smile and say something like, “Well, this is a challenge.”



2. Which girl should I ask for a date?

Abundance Mentality
When deciding on which girl you should date, the most important thing to remember is that there’s plenty of fish in the sea. One of the most damaging ideas that shy people have is that there is one perfect person for them. If you believe there is a soul mate for you, then you know have an incredible amount of pressure trying to please and date this one perfect match. This enormous pressure will lead to fear and failure in dating.

If you can change your thinking, so that you recognize that there are many people you could date and be happy with, then your opportunities are practically Unlimited. And the pressure a finding the right person is also eliminated, So now you can enjoy your dating experience.

Who is most likely to not be offended?
I’m tempted to say that you should ask out the girl who is most likely going to say yes to you. However, if that girl says no, that’s going to crush your spirit. Instead, try to find a girl who is unlikely to be offended by your invitation. Try to ask out the girl who will say no in the nicest way. Our goal here is not instant success, but minimize the pain of failure. After all, there are many girls you can and probably should ask out who you already know. So, start out with the girls who will hurt you the least if they do reject you. Over time, you will lose your fear of rejection. Eventually, one of them won’t reject you- hey you now have a date!

Who are you most comfortable with?
A second factor to consider is who you are comfortable with. This is why I almost always recommend starting with friendship dating. In fact, all around the world, the most successful dates are those between people who are already friends.

Now if you don’t have any friends who are girls, then you need to expand your social networks to include more women. There are lots of clubs, hobbies, and social activities where you can meet women in a friendly way. And after you’ve been friends for a few weeks or even a few months, then you’ll fell lot more comfortable around them and find it easier to ask them out in a date.

As you probably know I Am Naturally a very shy person. I’ve never gone out with a total stranger but I’ve often dated my friends. I’ve sometimes been asked by total strangers to go out on a date, but I am not comfortable with that.

Who is more desperate for a date than you?
There are a lot of women who are also very shy and they also want to go on dates. You can solve two problems with one action by asking out shy girls. It’s true that two shy people might have a difficult time having a quiet conversation together. But you can have a more activity focused date where you don’t have to spend a lot of face-to-face conversation. I once had a date with a shy classmate from Hong Kong, we watched a movie together and then talked about the movie afterward. It was a very comfortable date.

3. How to ask a girl out?

Start with what you have in common
When you’re thinking of asking a girl out, first identify what the two of you have in common. If you don’t have anything in common, this girl’s probably not the first one you should try to date. But once you do find a girl who you have something in common with such as a similar hobby or profession, then you can mention to her how much you two seem to have in common. It’s always helpful to use the word “seem” so that you don’t appear to be a know-it-all.

Point out an opportunity to do what you like together
The next thing is to bring up an opportunity to do something together that both of you like. The best way to bring this up is to make it sound like you were going to do it anyway by yourself or perhaps with some other friends and you are just inviting her to go with you. Perhaps the girl will show some interest in you and she’ll be happy to join you or she might even have a different idea, in which case, you can join her in her activity.

Tell them why you asked them in particular
Every girl is going to be thinking why is he asking me why me in particular. Tell her about some quality in her that you admire, especially something she feels is often unnoticed by others. That means you needed strong skills of observation and you may need significant time to identify what those hidden gems are. She will be very pleased and flattered and much more likely to say yes to your offer of a date if she hears this encouragement from you.

Make it easy to say no
Surprisingly one of the best dating techniques is to make your offer easy to reject. When you ask her out, make it easy for her to say no. If you feel a lot of pressure to get her to date you, she will notice this a get a negative feeling about you. So, you must first be willing to be rejected like it’s no big deal. When a girl senses your self-confidence, she will be much more willing to date you.

4. How to deal with rejection

Rejection is normal
Because we are avoiding manipulation and high-pressure techniques, you are likely going to experience a lot of rejection when asking girls out on a date. And that’s okay, that’s normal. Remember that there’s plenty of fish in the sea. A fisherman spends a lot of time throwing his bait out into the water waiting for the fish to strike. In the same way, don’t expect to have a high success rate, but you will never succeed if you are too afraid to try.

Don’t get hung up on one girl
If there is one special girl in your mind, I don’t recommend that you try to date her right away. Improve your dating skills and your social skills by dating other women first. After you can successfully date others, you will build up your self-esteem and then you’ll be better able to handle a date with that perfect girl you’ve been dreaming of. And if she still fails to see your charm, no is not never.

Never give up on yourself

It’s very important that you never give up on yourself. This is true in every area of life that requires persistence. When you’re hunting for a job you can’t quit after one or two rejections. You have to keep searching and searching until you finally find a job that satisfies your needs. And the same way, you need to keep asking girls out until you find one who not only says yes, but actually helps you have an enjoyable date. This is really the only way you’re going to find success.

No is not never
Sometimes a girl will reject you, but that’s not really her final answer. In fact, many times if a girl says no, she will relax, let down her guard and be more open to sharing about herself. You can continue to build up trust and perhaps in weeks or months in the future she, will be open to dating you. One of my friends said that she said that she would not marry a guy (who fell in love with her) if he was the last man on Earth. But this guy never gave up being her friend, so she eventually changed her thinking after a couple of years and gave him a chance. They are married now.

5. How to have a successful first date


Read my post on Basic Dating Tips

Focus on showing her a good time
A key to having a successful date is to sacrifice a little bit of what you want so that you can show your date a good time. And if this girl is worthwhile, she will also want to please you and see that you are happy on the date, also. A good date is not about how each one of you can get what they want. Instead, a good date is where each person tries to give the other person but that person wants. That’s the golden rule of dating. But of course, don’t go beyond your boundaries or don’t spend all your money on a girl.

Choose low commitment activities
Part of our strategy for shy people dating tips is to avoid pain or to minimize fear, especially of having your hopes and dreams crushed by rejection. You want to invite a girl out to do something where is easy for her to end the date early, if that’s what she feels she needs to do. If you make it easier for her to say it’s time to finish the date, then she will actually be more likely to stick through the date because she feels comfortable.

Lightly suggest doing something together in the future
Sometime in the middle or probably near the end of the date, find a polite way to suggest doing something again in the future. If you’re lucky, she will suggest that herself. But again this should be a low-pressure request, more of an observation than a petition. You can say something like, “Our time together is has been really great but really too short; I hope we have a chance to do something again soon.” (Actually that sounds kind of corny- try to do better than this.) And if you’re prepared, you can even recommend a second activity, especially an activity that you have discovered on your date that both of you would likely enjoy.


6. Pros and Cons of the top date activities



Restaurant, Bar, Cafe
The restaurant, bar, and cafe all have a very similar quality. That is where you sit facing each other talking, perhaps eating or drinking. This is a perfect way to get to know each other better and to share your experiences with each other. However, the negative side is that now you have a lot of pressure for conversation and since you’re shy you might struggle with this forced discussion.

And as a shy person, I don’t enjoy going to noisy bars; but if you’re okay with that, a bar could be a good spot for you. I would definitely go to the bar that I was comfortable with.

Generally having coffee together would be an excellent first date for a shy person because it requires less commitment and emotional endurance than a longer and more complicated date at a sit-down restaurant. What friend/aquaintance wouldn’t meet you for coffee? Your next date can be more involved.

Movie, Concert/Music Festival, Sporting Event, Amusement Park
These activities might be ideal for your date. That’s because they’re not focused on conversation or face-to-face intimacy. Instead, both of you together are facing outward towards some experience. And you can just add in conversation while you take in the sensations. The negative aspect of these venues is that you will miss an opportunity to be closer together and to get to know each other on a deeper level. Also, some of these activities take a long time and they might be more commitment than a woman is willing to invest on an early date. They can be an excellent venue for a second date.

Romantic Walk, Bike Ride, Beach

These activities are perfect for people who enjoy longer and sometimes quieter activities. This gives you a lot of time to not only experience your surroundings, but to gather up your thoughts and to think in detail about what you want to say and to reflect on what the other person is saying. The negative aspect of these places is that sometimes they experience can be boring, if one person isn’t really into the activity, or one person does all the talking.

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2 Responses

  1. Cinderella says:

    This is an interesting topic about dating but I feel you have touched also on fundamental principles of life in general, I have gone through being shy, moving to a new Country, learning to navigate in new invironments and surviving, trust me, one needs everything that you have outlined.

    I see where I was going wrong especially when it comes to dating but I have found an amazing guy and I have left go of my own fears and just want to enjoy my time with him, wether short or long term, I will enjoy myself.

    And thank you for the 6 tips.

    • admin says:

      I’m glad you found an amazing guy. Finding the right partner is the perfect way to overcome your fears and insecurities. The hard part for shy people is just getting the courage to take a chance on meeting new people and openly seeking a relationship. 

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