Online Dating Made Easy For The Shy At Heart


Online Dating Made Easy For The Shy At Heart
If you're shy, don't just send winks and canned flirts. Get noticed by doing this instead...

Communicating with your online dating love interest can be confusing. Should women send first emails? (Absolutely!) What do you write in a first email? (More on that below.) What about flirts, winks, and smiley faces? Should you send or respond to them?

And what if you're shy? Making the first move can feel daunting. I received this email from a woman who's perplexed about online dating communication:


Dear Sandy,

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


Dear Bea,

Flirts and winks and smiles — they're a quick and easy way to communicate with your e-match. Unfortunately, most men don’t respond to them. These canned responses are often viewed as lazy and impersonal.

It's okay that you're shy, but if you don't move a little out of your comfort zone in your online dating communication, you'll probably get ignored. So, how do you overcome your shyness? Try writing an email instead of a flirt. You can take all the time you need to compose a great email that will catch his interest. There's no pressure to be spontaneous or quick on your feet.


  1. MAKE IT PERSONAL. Pick out one item from his profile that grabbed your attention and include it in your email. I like to choose the most obscure thing he wrote. For example, if he writes that he's a doctor but has a secret desire to write a novel, ask him about that book. Then tell him that you get along well with creative men.
  2. 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. Make it pop. "Greek Isles on your bucket list, too?" or "Jumping on a Trampoline?" shows him that you read his profile and are commenting on something personal.
  3. ASK A GOOD QUESTION. One of the biggest mistakes people make is endng an email without asking a question. If you include a question at the end, he'll be more likely to respond. And no "yes or no" questions. For example, if a guy says he's an animal lover, don't ask, "Is that dog in the photo your favorite pet?" That will elicit a "yes" or "no" answer. Instead, ask "What was your favorite pet of all time and why?"
  4. DON'T SOUND NEEDY. Keep the tone casual, light, and fun in your first email. If you come on too strong, he might label you as needy or stalk-ish 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 just 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!

Wishing you success in love,


Click here for a copy of my FREE report, "The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)". Please 'like' my Facebook page for more tips on dating and relationships & updates on my weekly radio show. Want to know more about the Last First Date Inner Circle? Monthly Q & A calls, a private forum, and much more, all at a ridiculously low price. Join us today!

More online dating advice on YourTango:

Article contributed by
Advanced Member

Sandy Weiner

Dating Coach

Sandy Weiner

For 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.

If you are serious about finding love this year, there’s nothing like group coaching to keep you accountable and give you solid dating tools that work. In the Last First Date Inner Circle, you'll have access to two monthly topic-based Q & A calls about dating over 40, and a private forum for you to connect and share your experiences. All calls are recorded and transcribed, and you get a free chapter a month of my upcoming book. If you're a woman over 40 and want ongoing coaching support at an affordable rate, check out the LFD Inner Circle today. 

Location: Stamford, CT
Credentials: ACC, CPCC
Specialties: Dating/Being Single Support, Empowering Women, Online Dating
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