Women Dating Over 50: Are We in No-man’s Land?By Jackie Pilossoph


Jackie, I am approaching 50, and just over one year separated from my husband. As I look forward and begin to think about the possibility of future relationships, I can…..

Jackie, I am approaching 50, and just over one year separated from my husband. As I look forward and begin to think about the possibility of future relationships, I can see that dating over 50 might be difficult.

I notice that lots of people who were married for maybe 10 years or less seem to say…we got married early, found out it didn’t work, and then later remarried and have found long term, happiness with their next partner/spouse. What I also notice is that I don’t seem to hear any/as many happy stories about people (like me) who were married 20-25 years, got divorced, and then found happiness/ marriage, etc again.

It seems to me that lots of middle aged women get divorced and stay single. I might just be feeling sorry for myself but it seems to me that a 50ish woman is somewhere in no-man’s land for a future relationship. I may be generalizing but do you see the same thing?

Let’s face it. Men our ago want to meet someone younger. Younger guys aren’t a great fit. And, older men have interest but that isn’t really fair either. Maybe fair isn’t the right word. I would like to know your thoughts on the likelihood of 50 year old women finding a second life partner. Especially one in the same age bracket.

It’s really funny that I would get this email from you, wondering about dating over 50. Why? Because I’m turning 50 in 6 months, and I’m recently single again.

So, I guess what I’m trying to say in response to your asking my thoughts on the likelihood of a 50 year old woman finding a second life partner is: I HAVE NO CLUE, I’ll let you know when I find out? LOL!

I do have a few things to say about your email. The first is in regards to no-man’s land. I have always believed that 50’s is in fact, no-man’s land, whether you are single, married, divorced or widowed, the reason being that you aren’t really young anymore, but you aren’t old either.

I have had some issues while shopping for clothes in recent years, because all the clothing out there either seems too young or too old for me. Perhaps this same attitude applies when it comes to dating. If in your 40’s, it seems OK to me to date guys in their 30’s, 40’s or 50’s. But 50 is a different story. Guys in their 30’s are definitely out, guys in the 40’s might work, but they might want women in their 30’s or 40’s, guys in their 50’s definitely want girls in their 30’s or 40’s, and guys in their 60’s are just too old. (no offense.)

So, what to do? Being new at this, I’m going to go for just being my Gosh darn self and if someone wants to date me, great, and if they think I’m too old, then so be it. It’s all about believing you have a lot to offer someone, which I do. Am I perfect? Hell no. Am I kind of old? Yep. But that is what it is. I am me and all I can do is live life to my potential. And that’s what I’m doing.

Also, consider a wide age range when dating. I think as people get older, age matters less. So, not only does a large age range, (let’s say 42-57 perhaps?) increase the number of potential men for you, but I think you will see that age is only a number, unlike it was, say if you were 30, dating a 20 year old.

The thing that bothered me most about your email is this part:

What I also notice is that I don’t seem to hear any/as many happy stories about people (like me) who were married 20-25 years, got divorced, and then found happiness/ marriage, etc again.

You write: “found happiness/marriage etc. again.” The slash between happiness and marriage clearly indicates that you equate happiness and marriage, and that’s something I definitely don’t do. I equate happiness with: children, family, career, fun and surrounding myself with people I love and enjoy, whether that involves romantic love or not.

My bottom line is, I just want to be happy. I don’t have to be married for that to happen. I would ultimately like to be married again (I think) but anyone who reads this blog should know by now that I don’t feel marriage brings happiness unless you wait for the right person and/or the right time.

The last thing I will tell you to do is to slow down and don’t panic. Separated for one year is a very short time. Work on yourself. Work on healing. Have fun. Go on dates, but don’t force the serious relationship. Let it just happen.

Remember, 50 is the new 30! Is that cheesy? Who cares. I believe it!

I’ll leave you with this–Beautiful women who are over 50:

Michelle Pfeiffer, Andie MacDowell, Catherine Keener, Oprah, Madonna, Kim Basinger, Kim Catrall, Christie Brinkley, Diane Sawyer, Jennifer Grey

Best of luck!



Jackie Pilossoph

Divorced Girl Smiling offers advice, inspiration and hugs. If you want a Cinderella story, be your own fairy godmother. You're the only one who can pick out that perfect glass slipper!

4 Replies

Michael C. Craven April 06, 2015Reply

Thank you for your article. I found this interesting. -Michael C. Craven, Chicago Divorce Attorney http://www.divorcelawyerschicago.org/

darmok April 07, 2015Reply

I enjoyed your article too for many reasons. I left my wife after 25 years of marriage and 30 of being together. I could think of many reason but I had lost happiness a long time ago and tried to hold on. I didn't tell her what I was feeling for so many years and just felt it was my duty to be a good husband, father, and christian, don't worry about how I felt. Eventually I asked for a divorce and it devastated my wife. Choosing between making everyone else happy or yourself, including God, was a huge decision for me, I decided I needed to be happy. I am 58 and thought about living my remaining years up happy and just could not bare the thoght. A lot of people have their opinion on what I did and I am sure some, if not most, think I am a monster for doing this after so many years. I do have some guilt, guilt, for not letting my ex-wife know what I was thinking or what I was feeling. I do not think it would have made a difference bhe will never believe that. Anyway, I hope this is not true, women over 50 divorced never finding happiness again. I loved your statement of marriage not making you happy. I know it will take my ex years to get over our divorce, but I do wish her the best, sometimes more than what I wish for myself. I keep hearing people say it is easier for men to get over a divorce than women, hopefully not too true. I wish my ex would read your blog. We can talk sometimes but often it goes back to what I did to her and that is not a good place to be, ever. Thanks

nancy November 06, 2015Reply

darmok, you would have done your wife a ig favour had you left her many years before you did. that way, you would have given her the gift of the chance to find real love in an honest relationship and you as well could have gone on with your life.

LaLaverneLa January 23, 2016Reply

you would have done yourself and your wife a favor if you had spoken with her about your feelings. You did a large disservice to your relationship by just walking out with no reason other than you are not "happy", before leaving you could have undergone counselling either on your own or as a couple. You dont mention if you have children and how they feel about what you have done, or if you still have a relationship with them. You were exceptionally selfish and i suspect you may have other issues at play. I wonder if you are any "happier" now being on your own? or if you just enjoy not having any responsibiities to anyone else? What you did was a callous cop out and the karma bus will kick you in the ass sooner or later.

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