Dating OVer 40: The Unspoken Rule of Dating Still Holds True


Let’s say you meet a man who really catches your eye and gets into your heart quickly. You meet for your first date which becomes one of those marathons. Then your next date is just two days later. Seems like all systems are go and you both had a fabulous time. That’s great.
But this week he has to travel for business and he won’t be around much. So now you’ve had lots of intense get-to-know-you hours of fun and you are left hanging. What’s a woman to do?
My client Melissa just asked this question about a guy she met. She wanted to know what she could do to keep the ball rolling even while he is away. Should she text or email him? Should she call him? What can she do to secure her standing?
NOTHING. The most effective thing Melissa can do is absolutely nothing. NADA, ZIPPO, ZERO.
But why? In this day and age of equality, why can’t she just be honest, tell him she really likes him and keep the conversation going? Because that is just not how things work in the dating world. Sorry but this is NOT a good strategy.
Being direct works with business. I like you, let’s do business together. Money and services are exchanged. That’s great!
This has absolutely nothing to do with the emotional murky waters of dating. The idea of connecting is not about being direct. And that is because, even today, men still enjoy the chase. Which means pursuing him, putting your cards on the table, telling him that you’ve chosen him – will mostly likely make him run. Fast.
As a woman, in the initial phases of dating, the first 4-8 dates, your best bet is to laugh at his jokes, praise him for having a good time or choice of restaurants, lean in to show interest while he talks and thank him genuinely at the end of the evening. That is your job. Men like women who are easy to please and easy to be with.  Men like women who make them feel good, masculine and appreciated.

Most men don’t like women who chase. Buy tickets and ask them out. Call to set up the next date.

Men like to think dating you is his idea. If he likes you , he wants to show off his stuff and try to please you to win you over  That’s how the game works. You may be tired of this game, but just like the Eagles song called Hotel California, you can check out but you can never leave. Same goes for dating. You can try to pursue, but it’s likely to make him run.
How do you cope with waiting to see what he does then? Date several men at once. Why put all your eggs in one basket – or your sites on one guy? This is particularly true with online dating. Many men will disappear as fast as they showed up. Rather than setting your sites on one guy with potential, thinking and thinking about him, imagining your future together – meet and date many men. This is the best solution to keep your mind occupied while seeing if one of them pans out.
This strategy worked really well for me. The other thing I did which also worked really well, was avoid marathon dates to guard my heart. Instead, I kept the first few dates under 3 hours. In fact, my first dates were usually never mroe than 90 minutes. This helped me not get sucked in or hooked on a man too quickly.
Recognize the unspoken rule of dating and do your best to work within it. You may think it stinks. You may strain against it. You may curse the situation and defy it. But if you want to stay sane while dating, you’ll stop chasing men and let them chase you. It’s far more productive use of your dating time and effort. Increase your allure, if you like a man, smile and let him know what a great time you had. Send the right signals and you will attract and find the right man for you.


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.

3 thoughts on “Dating OVer 40: The Unspoken Rule of Dating Still Holds True”

  1. Helo, my problem is different. I’m in the market for a committed sex, with respect afterwards, but not much more, as I’m not in a place right now to do that. I can manage my emotions just fine, and what I find it that if I’m direct about it, guys take me for granted, always call back, but some after 3 weeks/one month, while I d like to have it more often. So I find the only way is to pretend I’m in for a relationship, just to get a regular, committed sex. Do you have any advise on that? I.e. Sleep with them earlier than I would have I looked for a relationship? Flirt more??

    • Hey Flower, My focus is committed loving relationships so I’m not sure about finding sex partners. Maybe you just need more than one to satisfy you? Or get a vibrator – that’s always available!

  2. Yay, Ronnie. Great post. I tried the “buy tickets and ask him out” trick once, and it completely backfired.

    The keep-the-date-under-3-hours rule is brilliant, too.


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