Making Sense of Online Dating Etiquette

Posted by in dating after divorce, dating in midlife, online dating after 40 | 0 comments

online dating etiquetteHi Sandy,

I am a midlife dater and confused about online dating etiquette. I sent two men a “smile” to indicate that I am interested. They both replied with a “smile”.

That was two days ago.

What does this mean and how should I proceed? Do I write a very non- specific email? I am a proactive woman and my instinct tells me to write an email, however older men appear to be a species that I cannot understand!

Thanks for your advice.


Dear Val,

Smiles, flirts, winks, instant messaging, or smoke signals; online dating has opened up so many options for how we communicate. It can be confusing. Send an email or a flirt? What if you mark him as your ‘favorite’? Is that enough to give him the message that you’re interested? What if he doesn’t respond? Does it mean he rejected me?

Take a breath! It’s really not all that complicated. You say you’re proactive, yet you’re sending a passive ‘smile’ instead of an email. A smile or flirt is much more passive than an email. How do you feel when you get a smile from a guy? Your email indicates that you are confused. I don’t blame you. A smile sent from on an online dating site doesn’t say much, does it?

I wrote a post about the use of emoticons in communicating with your date. I believe in direct communication. Write an email if you’re interested in a guy. Keep it short and sweet.

You can follow the easy email format I outlined in this post if you need a little help getting started. I’m glad to hear you’re a proactive woman. I think it’s important to take control of the things you have control over, and initiating an email is one of those things.

Tweet: Writing the first email is your chance at flirting with a guy.

You’re letting him know he piqued your interest and you want to start a conversation.

So, if you want to take some of the mystery out of online dating and are interested in making sense of online dating etiquette, write two emails a day to men who interest you. It will make much more sense to you once you start an email exchange instead of a smiley face exchange.

Let me know what happens!

: – ) Sandy


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