Dating Tips for Shy Guys - Cool Dating Advice

Dating Tips for Shy Guys

You are a shy guy with problems meeting women because you are too afraid to introduce yourself. This is fine I use to be shy especially around women. Having a more reserved nature about yourself is really hard to break that personality trait. I am not so shy now but how I changed would be tough for most of you to do.

You may be asking why can’t I do what you did to lose the shyness?

I actually joined a fraternity in college in my second year at school. The rigor you are put through when pledging made me come out of my shell making me less shy. I am outgoing, to begin with, but was pretty shy when I was younger with talking to women I did not know. You can make yourself change from being shy to being more outgoing plus assertive. You just have to really work at it. I know in the Four Hour Work Week by Tim Ferris he says you need to go up to random women every day and ask them out. Like really gorgeous women and this is to help you get out of being shy and to get you out of your comfort zone.

If your life is boring or maybe too easy going it’s time to do something about it. You may need to amp up your life by doing things like walking up to women and just talking to them. You cannot get a date sitting at home watching TV.

We will review some things you can do to help with dating and shyness.



We just talked about it but you can train yourself to be less shy. You can really start slow by just saying how to someone new every day. It can be anyone you see at a gas station or grocery store. Once you get good at that then you want to move up to say hi to only new women you see in everyday life. You keep doing this for months the shyness will start to subside. You need to get to the point where you can ask a woman out on a date and be confident in your approach.

Rehearse what to say and picture the outcome

Star athletes or top performers imagine the end goal. You can do this too if you really like a woman picture yourself asking her out and she says yes. You need to visualize what you will say and how you will say it. You can even carry flash cards with the information to rehearse. If star athletes do this to stay on top why can’t you do it to find and approach a woman you are interested in talking with.

Have women that are friends

You want to really combat your shyness. You need to have some women that are friends with you. Talking to women will help you with your shyness. The more you engage or try to understand the better chance you have of overcoming being shy when you want to talk to a woman you just met. The conversation with them will flow better because you have been talking to women friends. You just need to control the nerves and fear.

You just need to get to the first date

You don’t need to worry about the first date until you get the first date. You are probably asking what does that mean. You just need to ask her out for coffee or lunch. This is a great way for someone shy to get a first date. It is not like taking someone to dinner where it is a long time and more formal. Once on a date, you can ask questions and let her do all the talking. You just need to listen which is easy for a shy person.

Look good

You need to look your best if you are not great at speaking to women. When going out onto the town with friends or going out into situations where you might meet women. You need to at least look good in case you want to go up and talk to a woman. You need to be clean shaven, have good shoes and a nice shirt. You do this when you are going to places where you know there is a chance of meeting women that you may be talking to.

Body Shape

You need to at least keep yourself in good shape when trying to find a woman to date. Staying in shape and looking good will only help you to attract a woman. I am not talking make yourself look like a bodybuilder. You just need to stay in shape maybe lift some weights to have a great body for when you do meet a woman you like. She will be impressed by how in shape you are, it’s a great conversation piece and it will hopefully mask your shyness.

Body language

You are out with friends and you see someone interesting you would like to meet. You need to keep a good posture and when walking around keep your head up showing confidence. Do not stare at the floor when walking around. You want to be smiling and laughing with your friends. This makes you look like a fun person to be around. Everyone wants to be around someone or a group that is having fun. If you do approach a woman to talk to make sure you look them in the eye.


You have outgoing friends it can rub off on you. This will definitely help you to become more outgoing. I know that help me in the fraternity when I was in school. Some of the guys in my house were so calm, cool and collective. They talked to any woman and had no problems finding dates for the formal parties we had. If all your friends are shy like you maybe you need to find new friends or at least find another group you can go out with.

Change your thought pattern

You may run a ton of negative thought through your mind as you are thinking of approaching a woman you are interested in. Negative thought will only get you a negative outcome. That outcome is no women, no dates and no social life for you. You can battle your way out of it with some of the ideas we have listed above. You know what you are best at so put that at the front of your thoughts. A positive attitude, big smile and fun look on your face a woman is way more likely to engage when you introduce yourself.

Just be yourself

You want to come out of your shell so you can meet more women to potentially date. You do want to be yourself and not someone completely different. When we talk about becoming less shy we mean changing enough just to get to ask a woman out on a date. If you can’t get to a date you will never get married. You need to be who you are and just work at being more outgoing when meeting women.

Talking to women

You do not want to go up to a woman and be nervous talking to her.


You have to talk to her like it’s a long-lost friend. You would talk with an old friend in a laid-back manner not showing any concern. You need to do the same when going up to a woman you have introduced yourself to. This may not always work but way better than being stiff plus boring to talk with.

Rapid fire

Meeting someone for the first time you might be really excited. Do not fire off rapid questions in a way that she will not be able to answer them all. Slow down let her answer, then as soon as she has asked some questions you can counter with questions of your own.

Do not ask the old boring questions like:

  • What is your job?
  • Where do you live?
  • Where did you go to college?
  • Where did you grow up?
  • How much money do you make?
  • Why are you single you seem pretty nice?
  • How much did that cost?
  • Looking into the future do you want to have kids?

You need to really ask some better exciting questions like:

  • If you had $100 million dollars what would you do with it?
  • What is the craziest thing you have ever done? You can maybe say,” The craziest thing I have ever done was to go tandem parachute jumping with a buddy in college.” This will give them an idea of what you are looking for in a story.
  • If you only had 6 months to live what would you do and where would you go?
  • If you could live anywhere in the world where would it be? And why?
  • What is the number one thing you love to do?
  • What is a major accomplishment you are proud of?
  • What is one of the weirdest things you did as a teen?
  • Can you remember the best pick up line someone has used on you?
  • If you could go back in time and change one thing you did what would it be? Why?
  • Name something you wished you had known before going to college?
  • If you could pick one superpower to have what would it be? Why pick that one?
  • What is it that you would want to do for the rest of your life if money was no option? Would you work the job you had now or do something else?

There are hundreds of fun questions you can ask someone to learn more about them. You just need to dream up some more questions to add to the ones I have listed here. You can also check out our post on Funny first date questions.

Videotape yourself

You can videotape yourself practicing different questions and responses with a woman that is a friend. Doing this you can look at the video to see if you talked in a confident manner. This will allow you to see what you might need to correct and work on. If you have a bad habit then it will take 30 days to break that habit. You must work on getting better talking to women, asking questions and responding to questions asked of you.

Online dating

Since you are shy it may be best to try online dating. This allows you to create a profile to match your personality to someone similar of the opposite sex. You just need to be able to type out good messages to each woman you have an interest in. They will respond back if interested in you. The shyness is easier to get around when you are online because it is all done by email. The key is when you go to the next step with someone from meeting online to meeting in person you still need some face to face skills. You still need to get good at all the things we discussed in this post.

You can check out some of the sites we recommend to get started with online dating. You just need to check out our recommended dating sites and apps.

This should help you work through your shyness to find someone to date. There is someone for everyone no matter if you are shy. You just need to put forth the effort to connect with women. You keep at it sooner or later you will find the right woman for you.

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