Dating Over 40: When is it OK to Roll in the Hay?

Just the other day one of my clients wanted to talk about sex.  She had questions about when it’s OK to become intimate.  We discussed the old saying "Why buy the cow when the milk is free?" Does this archaic way of looking at sex still hold true?  Do men still think this way? 

Well, it depends.  It depends on the man, the religious beliefs, the timing, and many other factors.  Very conservative folks say you should wait until marriage.  OK, but that might be easier said than done.  Others say men don’t respect women who sleep with them on the first date.  So those are the two ends of the spectrum – but there is a huge amount of gray area in between and that’s where most people reside.

So, I’ll be addressing you "gray area" folks. When is it OK to roll in the hay?  It’s a totally personal choice.  If you are a very emotional person and know that you get attached after having sex, then it might be wise to hold off and spend more time getting to know your date.  Really learn about each other and see if the person is worthy of your heart, mind and body.   If you are a more casual type who can separate sex and emotional attachment, you have more flexibility because you aren’t as concerned about the outcome or rejection.

Honestly, there is no one rule.  Although, according to many men, there is the Three Date Rule – the idea being that the third date is the most likely time for a first encounter.  But who said women are on board with this rule?

For the ladies, I say, make your own rules!  You know yourself and what works best better than anyone else does.  Ask for advice and you’ll get a wide range of opinions and probably get confused as well.  In truth, only one opinion matters and that is YOURS.

Do what feels right for you.  You want to put off having sex  – good for you.  You feel comfortable going for it earlier – that’s your choice too. 

Back to the original cow-buying question and first date hay rolling. How do you know which men don’t care if you’re "easy" and which men are a more traditional? Ahhh, that’s the catch. You don’t know until you get to know him better.  And that is why I feel waiting a while is just smart.  That gives you time for some good data gathering to find out who he is, what he believes and how you two are together.  You really can’t lose when you hold off if you are looking for a loving, lasting relationship. 

So how long is a while?  I have one client who read some where that you should wait 30 hours.  That’s in person time and phone calls count too.  Others think the fourth date is fine, or the six, or the tenth.  Of course how many hours are in one date and do you count all of them too?  Let’s not get crazy!

Why not choose a number of dates that seems like a long enough time for you and go from there. Make that part of your Dating Protocol and don’t re-decide each time you meet a new man. If you stick to your own rules, it makes life so much easier, reduces stress, and gives you an easy out because you can simply say, "I’m not ready yet."

One piece of advice I can give you is not to tell the man you are dating WHEN you will be ready.  This is a negotiating error of large proportions.  Some men might find it a fun challenge to hang in and wait just for the sake of it.  Instead, keep your deadline close to the vest.  That keeps the tension going and leaves you a mystery – most men love a good mystery, especially of this nature. For more tips about Dating Protocol, read chapters 20-30 in my book MANifesting Mr. Right: It’s Never Too Late to Find the Love You Want.

My wish for you is that you find a good guy the next time out and never have to worry or think about this again.  Wishing you love!


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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