Dating Over 40: Responding to a Man from Who Winks at You

Online Dating Tips

Dear Ronnie – The Dating Coach,

I’m new to online dating and  Lately I’ve been receiving quite a few winks from men and I’m not sure how to respond. should I wink back or send an email? What do you recommend?

Been Winked At

Dear Been,

Overall, my recommended strategy regarding responding to men from online dating sites is this – mirror their actions. In other words, if a man winks at you, wink back if you’re interested. If he sends you a short email, email him back a brief exchange. The best way to interact with men from online dating sites is to reflect back to them what ever they are doing. That’s what I mean when I say “mirror” them.

Beware the Long, Non-Personalize Emails
However, if you get a very long email from a man who tells you all about himself, don’t mirror this. He has cut and pasted this long email over and over again to lots of women. Sadly, don’t feel flattered by a  long, non-personalized email.

Beware of the Email Pen Pal Who Never Gets to the Phone
With online dating, the point is to get to the meeting as quickly as possible. This is ideal versus becoming pen pals. Sometimes men want to email back and forth and never get to talking on the phone. Beware if this happens to you. He is either not emotionally available or in a relationship – these are the most likely scenarios. Emailing could be a way of cheating on a partner without actually cheating.

You don’t need any new pen pals. So many of my dating over 40 or dating after divorce coaching clients have fallen victim to this situation. Move on and don’t get caught up in the sweet emails that are so cute and sensitive. If after 2-4 emails, the man hasn’t asked you to speak on the phone, ask him to do so. It’s OK in this case to lead. If he hedges, drop him immediately and move on to find a man who might actually want to date you.

Beware of the Wounded Man Who Needs Your Help to Recover
I warn my dating coaching clients about this all the time. Please, don’t get sucked in to the Florence Nightingale idea of helping a wounded man through a rough patch. There will be no reward for your good nursing, except that he’ll likely move on to someone else. You’ll be a bad memoryof what he had to get over, rather than who he’ll come to once he’s relationship ready again.

Beware of the Man Who Loves the Phone But Never Meets You
 Ideally, you’ll email 2-3 times back and forth. Then speak on the phone briefly – say for 20-minutes. Then set a date to meet. A lot of my dating coaching clients end up talking on the phone multiple times for hours. This is similar to the pen pal situation. I had one male client who had a phone relationship for 7 months and never met the woman. He was crazy in love with her, but she had loads of excuses. Her Mom got sick, her job needed her, money was tight, etc.

She was a bundle of excuses and all I could imagine was – she was married/involved, much older/younger than she claimed or didn’t look anything like her photo. One thing is for sure – something was wrong with this scenario and his heart got broken by her empty promises. Please don’t let this happen to you.

Know the Fantasy Will Never Measure Up to the Real Man
Another issue with talking too long on the phone or even emailing too long before meeting is that you will create a picture of what the person is like in your mind from all your conversations. And trust me – a man will never be like what you imagine! Now you’ll have to get past the disappointment of how he didn’t measure up to your fantasy which never happens.

Leave a Little Mystery to Leverage Human Nature
So email 2-3 times, talk on the phone for 20 minutes, and then meet the man for no more than 90 minutes. The strategy is to leave him wanting more. When you let a little mystery exist, that makes a man curious to know more, so he may call you again. This is not manipulative – its just making the most of human nature. Whatever gets served up easily on a silver platter is not as desirable as something he has to work for.

Online dating is an amazing tool for meeting men you would have never had the chance to meet any other way. According to statistics, 12 % of marriages and 20% of relationships now start from web dating. Give it a try and be savvy with how you go about it!

Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

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