Winks and Flirts and Automated Responses: Yay or Nay?

Posted by in dating after divorce, single women over 40 | 0 comments

Dear Sandy,

How do you feel about winks, flirts, and other automatic ways of communicating online? I am shy and find this to be a comfortable way to let a guy know I’m interested.



Dear Shy-anne,

Letting someone know you’re interested through an automated response can feel safe and easy, especially if you’re shy. However, most people don’t respond to these little flirts. They don’t feel like enough effort was put into the communication. And they’re far from personal.

There’s nothing wrong with being reserved, in fact it can be a charming attribute. But if you don’t move a little out of your comfort zone, you probably won’t have much luck being noticed online. And that’s how you get dates.

So, how do you overcome your shyness? The good news is that you can beginning your correspondence through the veil of email. You don’t have to be spontaneous and quick on your delivery! Take all the time you need to compose an email that will catch his eye.

To make it easier, I have included some tips on writing a great email.

5 Tips for writing emails that will get you noticed:

  1. Make it personal. Pick out elements from his profile that got your attention and include them in your email. For example, if he writes that he’s energetic and optimistic and that’s important to you, say so. Tell him you are attracted to his warmth. Captivated by his smile? Let him know how he stood out from the crowd.
  2. Write a clever subject line. He’ll be more likely to open your email if you write something fun, smart, unusual in your subject line. Men who get a lot of emails may not open them all. Make him curious to get to know you. Your subject line is the first thing you say. Make it pop!
  3. Ask a question. If you include a question at the end of your email, he’ll more likely respond.
  4. Tell him that any response is welcomed. This way, even if he’s not interested, he’s more likely to give you an answer. Too many people have lost the art of common courteousy. If someone takes the time to write you a thoughtful email, please answer him or her.
  5. Don’t sound desperate. Casual is a good rule of thumb for your first email. Say something to the effect that you’re not sure, but at least on paper you seem to have a lot in common. If you come on too strong, he’s more than likely going to label you as needy and not respond. This isn’t a game show where you’re shouting, “pick me, pick me!” I like to think of it as more like an exploration. You are an adventurer, out in the wilds of online dating, and you’re trying to figure out if you’re compatible or not. You are as much the chooser as he is the picker. Don’t lose sight of that.

I hope these tips make it easier for you to take that first step and send an email, not a flirt or wink. Best of luck in your dating adventures! Let me know what happens.

Wishing you success in love,



Leave a Comment

Your email address will not be published. Required fields are marked *

AlphaOmega Captcha Classica  –  Enter Security Code

This site uses Akismet to reduce spam. Learn how your comment data is processed.