Wendi's take

Daniel's take

Dating Tips For The Shy 

When feeling a bit shy about dating, think about going out in a group. If you are interested in someone or panicking when asked out – say for example, “a bunch of us are going to the Greek Festival on Saturday. The food is fabulous and the music lively.  It will be a fun.  Want to join us?”  Or “Yes, I’d love to see that film.  Some friends and I are going Friday night, how about going with us?”  

You laugh and have fun without the pressure of carrying on a conversation by yourself.  You can add amusing or pertinent bits to what others are saying.   Even extroverts can get tongue-tied when talking to their crush. There is less of a feeling of being judged when in a group setting than being alone on a date.  This is a good way to get back in the dating game after a break up or divorce, when feeling a little unsure of yourself.  It is like the training wheels when learning how to ride a bike. 

Another way, is to go where there is community table.  There is a particular coffee shop I frequent after work, late at night. There is a community table, led lighting which changes color and DJ s playing edgy music. I meet people and have stimulating conversations. This can lead to dates or be just great way to make connections. 

Spend time with outgoing friends.  These extroverts draw people into their sphere, so take advantage of this situation. You start talking to individuals your friends are meeting, which breaks the ice.  You might click with an interesting person which can lead to a date. 

If avoiding dating because of being shy, explore options that include being with other people besides your date.

To learn more listen to our weekly podcast on iTunes or Spotify. Type in key word “dating coach” and look for the neon heart icon. 

How to Break into a Group to Meet a Woman You are Attracted To 

Restaurants, movies, and public places often require a group approach. Get used to it. Women, especially those who are attractive, are not found alone in public. Remember to have good social skills. Be respectable and acknowledge others in a group before locking in on your target. If you’re nice to the group, they will be nice to you, and may even encourage the woman you like to be nice to you. 

Make the group feel comfortable. Don’t stare at her. Don’t focus on her. Until you have made friends with the entire group, do not pay more attention to her than others in the group. Once you have made friends with the group, they will help you connect with the girl. Wait a few minutes until you have built comfort with everyone and then ask: 

So, how do you all know each other?” 

If there are guys in the group, you will quickly find out the relationship of the girl relative to them. If you discover she has a boyfriend, politely say: 

Nice to meet you all. Have a good night.” 

Sometimes the man you thought was a boyfriend will turn out to be a protecting friend called an orbiter. An orbiter is a guy pretending to be just her friend when secretly he wants something more. He's waiting for the right time to make his move, hoping to escalate his relationship with her to more than just friends. That will never happen. A girl values friendship more than sex. Once a friend, always a friend. That’s why you need to stay out of the friend’s zone as I cover in depth in my PDF, How to Meet and Talk to Women. 

After you’ve made friends with the group, that’s the time to start paying attention to her. If she likes you, try this: 

Hey, guys, I like your friend. Is it OK if I talk to her for a second? I’m going to borrow her for a minute. We won’t be long. I’ve got to be going.” 

It’s not a question. 

Get her email and phone number, then tell her to go back to the group. She will miss you. Call or text her later and ask how the rest of her night went. 

Dating During Covid-19 

Be creative when dating someone during this pandemic. 

Go outside on your dates. Go hiking, mountain climbing, skating, kayaking. A long walk provides the opportunity to learn more about your date. If you have dogs, plan on walking them together.  Many restaurants have meals for take away. This is the same for coffee shops. I meet up with different friends (one at a time) and we get our lattes and go to a nearby park. There are hardly any people there and we keep our social distance.  This can be done with a date. 

Do an activity together. Pick a theme such as cooking Italian pasta, making tiramisu and watching an Italian film.  The point is to be creative while following the rules of where you live during this corona virus outbreak.  This is the time to get through a boxed DVD set you have meaning to see. Or have a marathon of Netflix movies. 

Stay away from a crowd and have fun with your date. Keep hand sanitizer with you. Stay clear of people who are coughing.  Avoid a one-night stand and a goodnight kiss. Taking precautions such as good handwashing, getting enough sleep, eating a healthy diet reduces the chance of catching anything. Manuka honey is anti-viral and I take a teaspoon every day. 

The same rules apply as they did before the virus. Particularly for women, if you do not know someone well, then do not invite them to your place. Be safe. If you break off the relationship, better for them not to know where you live. Also, you do not want to get into a tricky situation where your date thinks you are on the menu.


Follow any and all local and national laws and precautions.

Get Out Of Your Dating  Past 

One cannot move forward in the dating world when living in the past.  Yes, process what did not work in your recent dating experiences, so as not to repeat them. Visiting the past is not the same as being a permanent resident there. When your thoughts and energy are directed to ruminating about old relationships, that hinders you from meeting a great man or woman now. 
There are signs that you are stuck in the past. 

  • Your conversations are about who you used to date. The one that got away 
  • Friends are tactfully changing the subject often (they are sick of you going on about old dates) 
  • Places and things keep reminding you about former dating partners 
  • You are not getting much enjoyment in life. 
  • You keep saying there is nobody interesting out there 
  • You fantasize about your past dates. 

Ways to get out of this rut: 

  • Avoid triggers, such as the coffee shop you frequented with an old flame. 
  • Listening to “our song”.  Avoid music that a former date enjoyed, at least for a while. 
  • Start doing new activities: painting, sports, travel 
  • Join some groups to meet new people, who can become friends or potential dates 

 When you follow these tips, you will be able to move on in the dating world.