Dating at Midlife/Older Woman


Dear Lauren,
I'm 50 years old and have been divorced for 2 years and have 2 adult children. My marriage of almost 20 years ended because my wife had an affair.

After the divorce, I joined some online dating sites in search of the woman of my dreams- not my parents' dreams, my children's dreams, or society's dreams.

As a younger man, I had always been attracted to older women. Nowadays,  I realize that younger men / older women pairings are fairly common. However, we're talking about men in their 20s dating women who are in their 40s.

I never hear about men in their 50s dating women 20 years their senior. That would be a middle aged man dating a senior citizen, or elderly woman. It just doesn't sound right. For the most part, men my age date younger women.

For the first year following my divorce, I did not date the older women that I truly preferred because I was afraid of what people would think of me. I dated women +/- 5 years my age. Needless to say, I wasn't happy.

It took a lot of soul searching, but I eventually discovered that I was hopelessly attracted to older women. And I realized I wouldn't be happy with a woman my age or younger. Problem solved? Nope! The problem wasn't solved because I hadn't come to terms with how to deal with the social consequences of being involved with a woman who was old enough to be my mother and a senior citizen. But that didn't stop me from starting to pursue and ask out older women.

As it turned out, most of the older women I pursued wanted nothing to do with a 50 year old man. Chemistry sorely lacked with the curious few who did go out with me. And then 5 months ago, I met Karen.

Karen is 71 years old, but her personality is much younger. She's old fashioned in some ways but not in others. Unlike most people her age, she's comfortable using smart phones and computers. She's a committed Christian and goes to church regularly, but she isn't a prude when it comes to having sex before marriage. She likes to have a couple of glasses of wine every night and she's a rabid chain smoker (cigarettes - not pot). I'm a non-smoker and would prefer her not to smoke for health reasons. However, her smoking itself doesn't bother me and I understand that after more than 60 years of smoking, she is probably going to smoke for the rest of her life, and I'm OK with that.

Obviously we date in public and I don't hide her from people in general. However, I have not introduced her to my children, my parents, or other family members or friends. On the other hand, I have met her children and grand children and her friends. She says she's ready to meet "my people", especially my mother.

I am "this close" to making that call to my mother. I honestly believe that not doing so could cost me the best thing that has ever happened to me since the birth of my children. I am in love with Karen. I'm sexually attracted to her and we have fantastic sex. I love spending time with her. And now I want the freedom to show her off as my woman. I want to be able to take her my parents' house for Thanksgiving and Christmas.

Karen's apartment lease is coming up for renewal in December, and I really want her to move in with me. We've talked about it and she wants to but introducing her to my family as my girlfriend is pretty much a prerequisite for that happening.

I have cold feet, Lauren. Please talk some sense into me.


Hi Derrick, What's the concern here? Do you really believe that what your mother thinks should be a deciding factor in your relationship? There are many people who will have and voice their opinions. The only opinion that truly matters is yours. Your happiness is on the line here. It doesn't matter what anyone else thinks. Your reservation to making that call might be an issue. You don't have to tell anyone if that's your choice but on the other hand to assimilate someone into your family would be a sign of acceptance. If you're having a hard time with that I would wonder if you're really comfortable with your own decisions. Maybe you need more time to figure it out. There is nothing wrong in my book for people to hook up and be happy. But they really need to understand what they're getting into. You may be financially secure with an older woman who may need nursing care sooner than you. She may be active now but she will decline faster than you. Are you willing and able to assume that responsibility? You also may need care before her, who knows? The question is, are you both committed to each other, no matter what? If you're answer is yes, then make that call, if not than give yourself time to figure out why you are hesitant and respect your decision. Either way it's okay. As long as you are comfortable with your decision.  

Dating at Midlife

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Lauren Stevens


I can answer all questions pertaining to dating, dating at 50+, online dating, health and sexual issues regarding relationships.


I have been a life coach and all expert coach for over 15 years.

I have founded and facilitated Life After Divorce a coaching program that promotes and enables life changing events. I also facilitated Transitions a support group for the traumatic experience of people going through divorce and the newly divorced.

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