Dating Over 40: Is Casual Dating Even Possible?

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

I am recently divorced and not sure I want to get into another relationship right away, but don’t want to sleep around either. In dating over 40, is casual dating even possible?


My gut reaction to your question is, why does dating have to equate to sex? Not just for dating over 40, but for any age? I look at dating and sex as going hand in hand if the chemistry and situation is right, but I think the two are mutually exclusive until that happens.


I think people put way too much pressure on themselves when it comes to sex. Having sex seems to be everyone’s biggest fear—men and women–in dating after divorce, which is understandable because it is a vulnerable, scary time where self-esteem isn’t at its best.


I have to wonder if there are expectations from daters when it comes to sex. I, personally have no expectations of sex or no sex when dating, and I don’t think there are any rules when it comes to dating and sex.


If someone tells me he or she went on a first date and had sex, I don’t judge. Do I think it is wise? In the majority of cases, no. But there are exceptions.


If someone says, “I’ve been out with this guy five times and we still haven’t slept together,” I don’t judge, either. One or both of the people have to feel like it is right to take things to a physical level, and if neither or one does, then sex is off the table, right?


The only thing I think is kind of gross, and again I’m not judging anyone else, but for me, I couldn’t sleep with someone who I suspect is sleeping with other women. I have written this before and people have written back and said, “Get over it!” But that’s just my stance. Everyone has to do what they feel is right for them.


Sex can be breathtaking and fun and exciting and mean the world with the right person. Sex can also be awkward and boring and considered a huge mistake if under the wrong circumstances or with the wrong person. Every situation is different.


My advice to you is to go out on dates with no expectations of sex. Assume you aren’t going to get physical, since that is how you feel right now, and that attitude will make you feel safe. Go on dates for companionship, interest, fun, to make new friends, and maybe even for a really nice kiss.


If you find yourself in a situation where someone expects sex, that’s his problem. You should never feel obligated or pressured to do anything you don’t want to do. Also, make sure you never put yourself in a unsafe situation, like going back to the home of a guy you just met, or having him over.


On the other hand, you might meet someone you really like and you might end up wanting to sleep with him. I’m sure it is hard to imagine, but I’ve seen it a thousand times in newly separated men and women. The spark ignites and it is totally unexpected. If and when that happens is dependent on the situation, the two people, and honestly, the stars. It’s beautiful to see, as a moment like that brings anyone who has ever had a broken heart hope and rejuvenation.


Just remember that casual dating means casual. It doesn’t mean casual sex unless you and the person you are dating wants that.


Take the pressure off yourself and just enjoy dating. As scary as it might seem, it is an exciting time in your life. The possibility of meeting people who become gifts in your life is at your doorstep. And dare I say that finding love is a possibility? Don’t rule that out. Statistics show that a couple falls in love every 93 minutes!


Honestly, I just made that up, but one thing is for sure. You aren’t going to meet him if you sit on your couch. Go date casually, and stop thinking too much about the pressure of taking off your clothes. Good luck!

Buy novels by Jackie Pilossoph



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

2 Responses to “Dating Over 40: Is Casual Dating Even Possible?”

  1. Lena

    I just found you and tend to agree with you about first date sex. Though with the caveat that dates these days tend to be hookups. I will add that my darling ex husband (still a friend, not good for relationships) and I had sex two hours after meeting on a beach and talking each other hoarse.

    You have to feel happy with your choice and perhaps experience gives you the judgement you need.

  2. phil carey

    ive recently become seperated after 12 years i have 1 daughter 10 yers old n 2 step children who are 18 n 15 i meet my wife when the step kids were only 5 and 3 years old my daughter of 10 is the only talking and seeing x has alfeady moved a guy in since we split less than 3 weels ago im at my wits end how do i cope


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