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Too Shy To Date

Dear Alex,

I am a single thirty-five year old big guy who would like to meet other big singles and date. But I am shy. I do not know how to carry on a good conversation. I have always been an introvert and avoided crowds because I don't know what to say. Do you know any methods to help me think of things to say during the conversation?

Shy Guy


Dear Shy,

Being shy can be a huge obstacle to meeting people. It's painful and often embarrassing. The problem all shy people face is this: the people you are trying to talk to think you don't like them. Most folks are so insecure, it never occurs to them that the reason you don't carry on a conversation is because--you're shy.

I once had a client who was shy to the extreme. If she had to talk to strangers, her voice broke, she became breathless, and she ran to the bathroom and cried. I am happy to report that she conquered this condition. This is what we worked on:

Go to a mall or a store.

The first step to losing your shyness is to get out of the house. Several times a week, go to a mall. Choose a different store to go to each time so the sales staff doesn't think you are a stalker. Your goal is not to buy anything but to do something your mother told you never to do. You are going to talk to strangers.

Plan your time.

If you want to get a date and learn to not be shy, get your calendar out. Write down the days you are taking up mall duty. If you don't plan this activity, it won't get done. Most of us avoid what is painful. Go out at least one hour per night, three times a week. Since you are a guy, it is best to start out talking to other guys who are strangers. Go to an electronics, computer, hardware, or sporting goods store. (For shy women, go to the beauty shop, women's clothing store, or department store that has housewares. You should start out talking to other women.)

Look for someone safe to talk to.

Scout the place for a friendly looking guy. Move to where he is and see what he is shopping for. Ask him about the product. Example: Do you know the best wrench, (shovel, hose, drill, generator) to buy? I don't know too much about them so how do you choose one?

Continue the conversation.

If the person is receptive, continue the conversation. The art of starting and following through with a conversation with someone you don't know is to ask a question, listen to the answer, and then respond to the answer with more than a "yes" or "no." What you are going to find is that most people love to talk about themselves, their family, their work, and their life. If anyone is rude or strange, move away and start over in another aisle or shop. Let nothing deter you.

Once you have mastered the art of starting conversations with guys, it is time to start working your way up to department stores where you will find older women shopping for housewares. Repeat the process until you feel comfortable with them.

You are now ready to start talking to women you are attracted to who may be closer to your age.

My shy woman client met a guy in a grocery store, they started talking in frozen foods, and they are still talking today. They got married.

Practice the above. You don't have to let your shyness rule your life. Good luck.


Visit for more tips, skills, and insight on dating, relationships, singles, and love. Subscribe to our dating newsletter from master single's coach, life coach, and syndicated columnist, Alex Wise. Copyright 2009-2020, Alex Wise. (Please note source if reprinting this article.)

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Posted on 12/23/20 8:10 PM.

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