Shy Guy's Guide To Dating Women
3.4 (6 ratings)
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Shy Guy's Guide To Dating Women

Practical advice to overcome shyness and social anxiety.
3.4 (6 ratings)
Instead of using a simple lifetime average, Udemy calculates a course's star rating by considering a number of different factors such as the number of ratings, the age of ratings, and the likelihood of fraudulent ratings.
89 students enrolled
Created by Demand Media
Last updated 12/2013
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Current price: $10 Original price: $30 Discount: 67% off
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  • 1.5 hours on-demand video
  • 1 Supplemental Resource
  • Full lifetime access
  • Access on mobile and TV
  • Certificate of Completion
What Will I Learn?
  • To become comfortable and relaxed with the prospect of dating
View Curriculum
  • None

In this course, you will learn a variety of tips and techniques that will make you help you become comfortable with yourself and dating. Through dynamic advice, dealing with aspects of personal well being and grooming to how to actually approach your first and second dates, this course will leave you feeling confident in how to move forward with your dating life.

Who is the target audience?
  • Shy Guys
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Curriculum For This Course
17 Lectures
What It Means to Be Shy
2 Lectures 13:44

Congratulations on taking a proactive approach to improving your dating life. Here you meet two mental health professionals, Dr Rupali Chadha, MD, and Alisha R. Johnson, Psy.D., who explain what it means to be shy, and how shyness is connected to social anxiety. Throughout the course, these doctors give you great strategies for dealing with shyness and dating.

Later in this course, you also hear from single women who discuss their views on dating shy guys and what they believe can make or break a date. We don't ask you to change your core personality or become someone you’re not. We just ask you listen carefully, take the time to perform the exercises and then apply the advice given. It may not be easy at first, but with practice and the right perspective your efforts will be rewarded with a rich and exciting dating life.

Key Points
  • Medicine views shyness as a form of social anxiety disorder.

    Shyness can sit anywhere on wide spectrum of anxiety disorders. It can be extreme, as in cases of social phobias, or very minor.

  • Symptoms include:

    Excessive fear of social situations — Avoiding social situations — Intense anxiety or distress in social situations — Fear and anxiety that interferes with your normal routine.

  • Shyness is treatable through therapy and personal work.
Preview 07:00

In this lesson Dr. Chadha explains that shyness falls on a spectrum; she covers its medical definition and talks about how common it is in the population. She also discusses how personality and shyness are linked to the physiology of the brain and body, the various types of shyness, and the treatments and modification exercises that exist to address them.

The goal of this course is to help you apply some proven techniques to transform yourself into someone with the confidence and skills to get that first and second date. Again, get ready to work! You'll need an open mind, a willingness to try new things, and a little patience. A level of confidence and optimism about yourself that you never thought possible is within reach!

Key Points
  • Varying degrees and types of shyness exist.

    Shyness can be linked to personality and biology, or triggered by social experiences.

  • Shyness affects all types of people.

    Celebrities like Chris Rock and Will Ferrell prove it can be overcome.

  • You’re not alone.

    Forty percent of Americans identify as being shy.

Preview 06:44
Overcoming Shyness
6 Lectures 40:20

In this lesson we explore the causes, types, and degrees of shyness, as well as the basic approaches to relieving it. We examine the possible roots and triggers of your shyness, and our experts explain how positive thinking and self-affirmation work with the pathways of the brain to support positive feelings. They teach you how to use these affirmations moment-by-moment on a date to get past whatever may be triggering your shyness.

At the end of the lesson, please review the Action Items listed below. You will be asked to take a few minutes with pen and paper to do some objective self-reflection; try writing out answers to the questions provided. Take your time, and when you are done move on to the next lesson, where we get to work on Basic Social Skills.

Materials List
  • Pen and Notebook or Journal

    You may like to keep a special notebook or journal for exercises and course notes. You can jot down your thoughts and refer back to your notes as you work through the course.

Action Items
  • Take some time for self-assessment.

    Reflect and consider the following possible causes of your shyness. Are you self-conscious about your appearance? Do you sometimes not know what to say in social situations, or when meeting new people? In what particular scenarios are you easily embarrassed? Do you fear rejection by women, or fear being teased? Think back through your life. Do you recall any social experiences where you felt ashamed, self-conscious, or anxious? If so, write about what happened.

Key Points
  • There are four perspectives of shyness:

    Disease: Genetic — Behavior: Circumstantial — Dimensional: Influence from close friends and relatives — Life story: Incident in your past.

  • Positive self-affirmation really works!

    Your thoughts can literally rewire your brain so you think differently overall.

  • Specific potential causes:

    Appearance conscious — Not knowing what to say in social settings — Embarrassing social experiences — Rejection by women — Relatives shy — Highly critical parents.


In this lesson, Dr. Johnson talks about smiling, making eye contact, faking it if you have to, and appearing interested. She explains the importance of practicing these confidence-building behaviors and stresses that a friendly smile, a soft interested gaze, and friendly body language go a long way to show that you are open and interested.

Practice these key behaviors in low-pressure situations, and take some time to reflect on your progress. You might want to jot some notes in your dating journal about what worked and what didn't. Practice makes perfect and prepares you for that unexpected moment when you really want to say hello.

Action Items
  • Practice smiling, making eye contact, and saying hello.

    In your day-to-day life, take a few days to practice smiling, making eye contact and saying hello to strangers as well as people familiar to you in your day-to-day life. Then take some time to reflect on your progress. You might want to jot some notes in your dating journal about what worked and what didn't.

Key Points
  • Practice is key to enhancing self-confidence.

    Build better social skills by interacting with more people, making welcome eye contact, smiling more, saying hello, and practicing.

Basic Social Skills

In this lesson Dr. Johnson examines the art of becoming a good conversationalist and helps you identify opportunities to have great conversations. Here, you get ideas for starting in low-pressure situations, and you learn to play to your own strengths. You also hear some great ideas and guidelines for conversation topics and strategies for striking up practice conversations.

Additionally, Dr. Johnson talks about the Rational Emotive Behavioral Theory developed by the famous psychologist Dr. Albert Ellis, and the outcome of his experiment that involved talking to 100 random women within a one-month period. Last but not least, we cover the importance of practicing active listening skills and the keys to active listening.

Action Items
  • Practice conversation skills and active listening.

    Find a close friend and practice the basic conversation skills covered in this lesson. Be sure to also practice active listening. Set a time limit for your talk, and when it is over, ask your friend for feedback. Don't forget to jot down what you learn in your notebook or journal. Be sure to note what you did well and the areas where you would like to see improvement.

Key Points
  • Basic Conversation Skills:

    Social skills are essential to meeting women — Practice in low-risk settings — Play to your strengths — Listening is even more important.

Basic Conversation Skills

Here you learn a few more conversation tips, such as why it's good to stay up to date on current events, how to find interesting things to discuss, and what "hot button" topics to avoid discussing. You hear from a few single women about what they look for in stimulating date conversation, and then Dr. Johnson discusses the proper levels of personal disclosure and how to keep conversation rolling on a first date.

The power of storytelling is covered and includes tips on how to practice telling your interesting story without getting bogged down in the details. You also learn the personal value of striving to set others at ease and how to do it like a pro.

Action Items
  • Think of some stories to share.

    Take some time to think about a few fun or interesting stories from your life that you think would be fun to share on a date. Pick one or two and then write them out or outline the main ideas. Practice telling your story a few times to yourself or to a friend. Think about ways you can keep it short and free from extraneous detail but also entertaining.

Key Points
  • Have great conversation starters.
  • Stay away from controversial topics.
  • Make people feel comfortable.
More Tips on Conversation

In this lesson, women talk about the importance of confidence and how they really define it -- they might surprise you! Dr. Johnson suggests a number of fun activities to help you broaden your social skills and meet women with common interests.

You are also asked to take stock of your job, friends, and social activities. Therefore, this lesson includes an exercise under Action Items geared to help you examine how you spend your time. After you perform your Action Item, please move on to the next lesson, Grooming and Attire.

Action Items
  • Take stock.

    For this exercise, grab your pen and dating journal or notebook and write down how you spend your typical week. Work, play, hobbies, everything in between. Honestly evaluate areas in your life that you feel could use some improvement. We want to help you get out of your shyness shell, to have you out and doing things that build your social confidence, and to get you in the right place to meet women with common interests. The more people you meet the more potential dates you will encounter.

Key Points
  • Build a Social Life:

    Try new activities — Join sports teams — Volunteer — Take classes — Try adventure groups.

Social Life

This lesson shares tips for evaluating your personal style, taking inventory of your wardrobe, and presenting the most pleasant put-together you. Learn what little things you can do to appear youthful, stylish, healthy, and attractive to women. Taking minimal steps to appear stylish and well-kept will go a long way to getting you a second date.

You will be encouraged by what our single women say about attraction and appearance, and the importance that having strong confidence plays in creating a genuine attraction. After listening to their perspectives on dating, take a long look in the mirror and proceed to the Action Item for this lesson.

Action Items
  • Taking a look in the mirror.

    Ask yourself, "If I were a woman, would I want to date me?" Check out your closet. We're not saying throw away your favorite 10-year-old concert T-shirt, but make sure you have a nice fashionable shirt and a clean unworn pair of jeans or pants to pull out for dates. If you're game to really ramp up your look, talk to a stylist about a new hairstyle, see a dentist about improving your smile, get a manicure, wax wild eyebrows, and try wrinkle-fighting skincare products for men.

Key Points
  • Grooming and attire matter.

    Look your best to feel your best — Try some new clothes — Get a haircut — Hit the gym.

Grooming and Attire
On the Road to Dating
3 Lectures 16:26

This lesson calls on you to pull together all the skills we've covered and put them into play by starting small talk with women you don't know. Having mastered eye contact and smiling, and with an arsenal of conversation starters, you can now start practicing in everyday non-threatening situations.

Here you learn the ideal places and people for striking up small talk; you are given ideas for what to say and tips for how to practice in a secure environment. Dr. Johnson explains the importance of preparing mentally, role-playing, setting small attainable conversation goals, and building up to more in-depth interactions. This practice will help increase your confidence, so don't move forward until you have completed your Action Items.

Action Items
  • Try striking up small talk with a woman you don't know.

    Standing in line for coffee, waiting in line at the lunch counter, shopping at the grocery -- use everything you have learned thus far and try some small talk with a woman you don't know. You may want to write in your dating notebook or journal about how it went, what worked, and what didn't.

Key Points
  • Become more comfortable with women by:

    Practicing — Not focusing on the outcome — Remembering Albert Ellis — Not avoiding interactions — Engaging people in conversations — Setting small goals — Letting it happen as naturally as possible.

Becoming at Ease With Women

In this lesson, we dig into the nuts and bolts of asking a woman out. We include some great tips on how to know if a woman is interested, how to improve the odds that she will say yes, and how to simply ask for the date. Dr. Johnson discusses verbal, social, and body-language cues to help you gauge a woman's interest in you. Dr. Chadha discusses the importance of addressing your personal issues and being emotionally ready to date. Dr. Chadha is followed by several of our ladies, who share how they like to be asked out.

Key Points
  • Getting the Date:

    Take the leap — Learn to read verbal and physical cues — Be confident, or at least seem confident.

Sometimes You Must Just Ask

This lesson deals with encountering, coping with, and understanding rejection. Dr. Chadha reviews the application of strategies you learned earlier about tossing out false beliefs and examining the root causes that hinder dating life. She explains how to examine any fear of rejection and attack it head on.

Later in the lesson, our singles answer the questions “How should he not approach you?” and “Has a guy’s shyness prevented you from dating him?” You also come away with tips on how to gracefully accept rejection, and you discover why being nice and understanding might pay off in the long run.

Lastly, you are taught to examine your moments of rejection, to consider factors both within and totally out of your control, and to use those insights to reduce your chances of rejection moving forward.

Key Points
  • Dealing With Rejection:

    You can do everything right and still be rejected — Don’t blame yourself unless it really is your fault — Be a gentleman — Reflect — Stay positive!

Dealing With Rejection
Preparing for the Date
2 Lectures 09:36

In this lesson you will get some great tips on planning a first date. There is a lot to consider, and Dr. Johnson offers some great first-date advice. She covers how to choose the best time, place, and possible activities suited to you both. She explains what to avoid and shares how open-ended planning can help move a date that is going well into a more intimate setting.

Next, our singles share their ideas for ideal first dates, their preferred setting and tone, and what they hope a first date will achieve when it comes to romance.

Action Items
  • Field research: Ask your friends.

    Ask your friend to tell you about some of the best first dates they ever had. Learn what they did, where they went, and what they remember most. You can steal their ideas or use them as inspiration to come up with some killer date ideas of your own.

Key Points
  • Planning a date:

    Set the day, time, activity — Keep it simple — Find a good place to talk — Don’t overthink it — No big, fancy dinners — Avoid shows and movies — No extreme sports.

Planning a Date

This lesson addresses how to handle pre-date jitters. Most everyone gets them, and our expert Dr. Johnson offers special advice on preparing for a date - this includes being aware of proper social etiquette. You also learn some great strategies for calming those nerves, like remembering that your date is in the same boat as you are.

In this section you are also reminded to think from your date's perspective, and you discover some easy activities you can do to prepare, stay calm and maintain confidence as you get ready for a comfortable first meeting.

Our singles also talk about how they themselves deal with pre-date jitters, the advantages and risks of using alcohol to calm your nerves, and when it's NOT OK to make the first move.

Key Points
  • Don’t focus on the outcome, just relax and have fun.
  • You’re on equal ground, as you are both testing compatibility.
  • She likes you, so continue to be yourself.
  • Anticipating the date can be nerve-wracking.
Pre-Date Jitters
Now You're Out There
3 Lectures 11:42

Congratulations, you have arrived! This lesson walks you step-by-step through the many dos and don'ts of first-date etiquette, conversation, and interaction. You've practiced and rehearsed, so now it's time to step onto the dating stage and show your stuff. In this lesson, we review how to put together your best self, inside and out. We revisit using eye contact and smiling, and we remind you to use the techniques you learned earlier to set your date at ease.

Dr. Johnson also shares some great tips on asking questions, showing your less serious side, picking locations right for you, and strategies for dealing with nerves during the date. Later in the lesson we hear again from our singles on their ideas for what to do when you feel nerves or shyness creeping into your special night.

Key Points
  • Use what you’ve learned.

    Make eye contact, focus on her, stay interested, listen, and learn.

  • Look your best, be generous, and give compliments.
  • Remember the main point is to get to know her.
On the Date

At some point on the date you will begin to get a feeling that it is going great, OK, or not so good. This lesson helps you assess whether to ask for a goodnight kiss or that second date at all. Learn to come off as a gentleman regardless of whether a second date is in play, and discover how to let your date know if you are interested in seeing her again.

You also hear from our singles on the best way to let a woman know you like her, and who should make the move for that first kiss.

Key Points
  • You can usually tell if it went well.
  • If you want another date say so.
  • If she wants to go out again but you don’t, be honest but kind.
  • If you want to go out again but she doesn’t, don’t push it.
Assessing the First Date

Once you have the second date, then the ball is in your court! From here it is up to you to take what you learned on the first date about your new friend and apply it to the second. date. You will take away some ideas on how to plan a second date that aligns to her interests and that shows you are thoughtful and paying attention. One last time the wonderful women, that have shared so much throughout this course, open up to share their personal deal-breakers. Finally as a special treat, we hear from one of them on how she got the shy guy in her life to propose.

Key Points
  • Use what you learned on the first date.
  • Relax: You’re doing it right.
  • Continue to be yourself.
The Second Date
Final Word and Resources
1 Lecture 00:00

You've now gained insights from doctors of psychology and psychiatry about what causes shyness and ways to mitigate it, and you have practiced practical exercises to overcome it. You've heard women's unique perspectives on dating shy men, and you know what women really look for on a date. You've mastered the tools you need to comfortably approach women, you've gained strategies for striking up conversations, and you have plenty of ideas for planning and enjoying dates. So what are you waiting for? Get out and start your new, exciting dating life!

Epilogue and Further Reading
2 pages
About the Instructor
Demand Media
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Demand Media, Inc. is a leading digital media and domain name services company that informs and entertains one of the internet’s largest audiences, helps advertisers find innovative ways to engage with their customers and enables publishers, individuals and businesses to expand their online presence. Headquartered in Santa Monica, CA, Demand Media has offices in North America, South America and Europe.