great winkAre You Winking Your Way Out of a Date?

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,

In online dating, expressing your interest through an automated response can feel safe and easy, especially if you’re shy. However, most people don’t respond to these little flirts. It can come off as a cop out, like you didn’t put in enough effort to warrant a response. These flirts and winks are far from personal.

There’s nothing wrong with being a bit reserved. In fact, a little shyness can be a charming attribute. But if you don’t move 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 and peek out from behind the winks and automated responses? Email! The good news is that emailing your love interest is not as scary as talking by phone or in person. You don’t have to be spontaneous or quick on your delivery. Take all the time you need to compose an email that will catch his eye.

Here are 5 Tips for writing dating emails that will get you noticed

1. Write a clever subject line. He’ll be more likely to open your email if you write something fun, smart, or unusual in your subject line. Men who get a lot of emails may not open most of them. Make him curious enough to want to open yours. Your subject line is your first impression. Make it pop. Here are some possibilities: “From a fellow foodie,” “Seeking co-author,” “Your avocations intrigue me,” “Bowling on a first date.” All of these subject lines are in response to something in the man’s profile. Pick something that stood out for you and use it as a way to capture his attention.

2. Make it personal. For the body of the email, once again, pick out specific elements from his profile that got your attention and include them. For example, if he writes that he’s energetic and optimistic and that’s important to you, say so. Captivated by his smile? Let him know how he stood out from the crowd.

3. Ask a question. If you include a question at the end of your email, he’ll be more likely to 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 courtesy. 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. If you come on too strong, he might 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 the first email as 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, and let me know what happens.

Wishing you success in love,


I want to know: what’s been your experience of sending emails online? What percentage get opened and responded to? Please share your experiences below.

For more midlife dating advice and a copy of my FREE report, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

Please ‘like’ my Facebook page for exclusive articles and tips on dating, relating and mating in midlife, updates on my weekly radio show, and great conversations about dating.

5 Tips For Writing Dating Emails That Will Get You Noticed was last modified: by

Sharing is caring!