5 Reasons why Older Single Women Give up on Men

Older singles disillusioned with dating and relationships

Trying to be an old-fashioned girl

Last time I hung out with my girlfriends, the talk turned to why we have a better time hanging out with each other than with the guys we’re dating. Several of the girls had recently broken up with their boyfriends. A couple others were seriously considering it. Only the ones who’d been married a long time were happy in their relationships.

And we are not alone.

 If you are an older single, you are officially disillusioned.

So says the CEO of eHarmony:

“One of the things we’ve learned is that people in their 20s and 30s who have income are very happy to spend more in the search for a more enduring relationship…When you’re in the 40s and 50s that changes. You can see the impact of relationships that don’t work out. You see bitterness. They believe less in compatibility. They are interested in companionship but not marriage.”

But, if  you’re reading this blog, you probably already know that.

Mr. eCEO adds that older singles are reluctant to pay the $57 monthly fee to use eHarmony.  If  they don’t think they’re going to find love, why pay for a losing proposition.  (And there are many much larger free sites).

So, here’s five things that are disillusioning us womenfolk:

1.  Time apart: My girlfriends are really independent.  They want to live on their own, setting their own schedules with plenty of time to pursue their separate interests.  They find some middle-aged men to be clingy, wanting to spend more than a couple nights a week together or expecting ultimately to live together.  We want to be independent people who meet at intervals to share experiences.  My friends don’t demand more time from each other than we have (willingly)  to give.

2.   Empathetic Listening:  Most guys don’t listen the way that women do.  It’s like they can’t empathize with what we’re talking about.  My best advice for friendship or dating: Listen carefully to what your prospective friend is saying, then ask interested questions about it.  If someone is passionate about something, there’s a reason.  If she lives to decoupage photographs of kittens to wastebaskets, ask how she picks the photos.  Don’t immediately move on to talking about your hobby of tracking down rare dung beetles. My friends and I listen to each other’s problems and we offer to help out with things. It’s mutual and empathetic.

3.    No Hidden Meanings: Dating is all about the subtext.  When is it ok to leave some stuff at your place?  If we spend holiday time together, does it mean we’re committed?  How much time together looks too clingy.  It’s aggravating.  With friends, you get to hang out without worrying what it looks like. Girlfriends have invited me to share their holiday meals when I told them I had no plans. They didn’t worry it meant we weren’t still seeing our other friends too. When I asked a guy I was dating to include me in his family Thanksgiving because I had no one to spend it with, he said he was afraid of how it would look. I never saw him again.

4.    Respect for Differences:  Dating as adults, we’re already formed.  My girlfriends and I respect each other’s differences and don’t try to change each other.  Our idiosyncrasies are what make us who we are.  But the men I’ve dated have tried to show me their choices are superior.  They wouldn’t live in the lovely suburban town I live in. Too staid for them!  They’d be more adventurous. They’d move after losing a spouse.  They’d change houses and get rid of his stereo system.  Here’s the thing: I’m too polite to say what I think of their life choices. I  just move on.

5.  Money:  My friends and I split everything.  And we understand if one of us says something is too expensive.  But we go to nice places, order good food and do fun stuff.  A few of us have dated really cheap guys.  I’m good with going to inexpensive places, but not bad ones.  There are plenty of cool, reasonably priced restaurants. Don’t tell me I’m increasing the bill when I order a glass of house wine or dessert.  I can get relatively cheap take-out, put it on attractive plates at home and serve it with nice wine.  But I’ve never dated a guy who does this, he’ll just choose a bad (but cheap) restaurant.  My fiends get the idea that instead of trying to have a really small tab, we can just stay home.

My Overarching Message

Let’s pretend our dates are our friends, people we really like and care about. Just as they are now. Not “if only” they were different. With compassion and empathy for  their foibles.  And with kindness instead of concern over what things “look” like.  Then we can end all these ridiculous distinctions.  And my stunning, intelligent girlfriends may yet want to date again.  Comments, my friends?

Open for Advice

I’m trying diligently to post once a week.  But the drugs of the eighties have staunched my creative abilities. So, if you have a problem or issue you’d like me to address here, let me know! if I think I can be of help, I’ll tackle it in my weekly post.

Respectfully, and with love,




  • Therese says:

    I think there is an unwritten rule somewhere that widows should move out of their marital home after their spouse passes away. A couple of men have asked me about that. I love my home and don’t see a reason to move. I have changed many things since my husband passed. It holds warm memories of my spouse, but so many other wonderful past and current memories. I guess they think if I move to a new environment I will not miss my husband as much….so silly.

    Thank you for the great article. It makes me feel good that I was not the only bad girl in the 1980’s.😀.

    • Debbie says:

      Thanks for the awesome comments. I too have great memories associated with my lovely home I put a lot of effort into fixing up. Maybe men feel threatened being in our prior husband’s “turf.” (I was a bad girl on weekends, a lawyer during the week).

  • Nancy says:

    Debbie, I just love everything you write, and this is no exception. After years of increasingly disappointing dating after my husband died, I came to many of these same realizations and started doing what really fulfills me. I’m having a great time! I’m still young (er), and definitely haven’t “given up” but by shifting the focus I have a lot more time for myself, my children while they are still home, and friends. I like your positive attitude and wry observations. Thanks for telling it like it is.

    • Debbie says:

      Thank you so much Nancy! That is just wonderful to hear! This post came out of my last two weekend dinners with my girlfriends. When I resurfaced bit after George died, I focused on dating. It took me too long to realize I needed to create a life with friends and activities I loved. The “guy” thing wouldn’t make things better.

  • Gilbert says:

    Wow, good to know information for this middle age man who’s wife passed a few months ago but hasn’t started dating. I would like to go out with a nice woman in the near future, preferably a woman who is around my age. It would be so nice to have a conversation with a woman again and not my teenage boys. However, I have a question to ask. While, I am not disillusioned as it pertains to marriage I have no wish to marry again. I loved being married because of who I married to and not the idea of marriage. Would my not wanting to marry again be a deal breaker for many women?

    • Debbie says:

      I don’t think that not wanting to marry again would be a deal breaker! Several of my girlfriends were saying that they don’t want to get married again either. Rather, they want a man who respects their independence and doesn’t want to combine all aspects their lives. Your not wanting to marry again would be plus for some women. All that matters is being straight forward about what you want when it eventually comes up. And being cautious and taking care of yourself when you feel ready to date again.

      • Gilbert says:

        Thanks, Debbie I appreciate your advice. If you can’t tell I’m extremely nervous with the aspect of dating. Nonetheless, I keep moving forward with life and getting my life in order.

  • Kevin says:

    Nice piece as always, Debbie…

    Those men sound just like the WOMEN I date…maybe I should meet your friends. I have many similar complaints, and have kind of stopped working at it (but still interested).

    It’s hard being “older”, “set in our ways”, but finding the right match is still the same daunting task: finding someone like you but different from you, in all the right amounts.

    Sounds impossible.

    Sometimes we just want the impossible….

    • Debbie says:

      Thanks Kevin. And very well-written comments. Maybe dating brings out the critic and stunts the empathy in both genders. It is a daunting task. I used to think there could be several right people for someone, but I’m more cynical these days. And yes, we want the impossible but sometimes we get what we need. (Cue The Rolling Stones in the background).

  • Bob H says:

    Debbie, I’m 53 and I was married for 14 yrs, got divorced and tried to get my shit together and accept my faults, remarried and I had a solid relationship. So, I re-married and I finally had met someone that got me and I got her, then, life hits after 7 years and she passed away 4 years ago leaving me with a 5 yr old to take care of. I’m still officially single, doing the on-line dating thing on and off with some success and I’ve found out that people in my generation have some serious barriers to finding love again. Here are my dating observations regarding women in their late 40’s and early 50’s (I’d hate to find out how women see men at this stage, LOL):
    1. Most of the women I’ve dated are educated with serious careers
    2. Emotionally still trying to get over what awful relationships they had with their ex-husbands
    3. Trying to prove that they can do it on their own
    4. Their children are out of the house (pretty much) and they want nothing to do with a man with a 9 yr old (many women start off saying they’re ok with it but really their not)
    5. Have a strong set of women friends as support
    6. This is the kicker, they really have no idea what they want regarding commitment. Many women want to be in a happy relationship, friendship, good sex, and someone that will listen and not tell them how to fix their life. Sounds good, but, the ghost of Christmas past rears its ugly head and the memory of the last failed relationship appears and it stops them in their tracks. So, what is a girl to do? Sorry if I’m generalizing, but, this is what I’ve run into these past few years.

    Back to your blog, let’s not forget the overweight guy who posts his picture from 10 yrs ago when he weighed 30 lbs. less on his on-line dating site to help find a women so he can fall back into the same old crap he did before. Oh yeah, he hasn’t had sex in 2 years because his ex had cut him off because he was such an asshole. Lastly, he wants a long term relationship, but, the women he meets says they want the same thing but their really not sure. What a mess we have created. My advice to all is make sure you have clear goals and know what you want before you start dating because it’s not fair to all the parties. Men, learn how to listen and care about what the other person has to say, and women, stop looking back at your broken relationship or broken heart and trying to prove you don’t need anyone.

    I know you are probably saying I’m cynical, but, at least I can laugh at myself and try my hardest to respect others life decisions. So, at 50 we are who we are and we need to learn how to compromise and accept others life styles. Maybe finding “The ONE True love “ is not in the cards, but, having someone that you enjoy being with, makes you smile when you’re having a bad day, and hearing that you look great even though you know you look like you were run over by a truck is what is important in life.

    • Debbie says:

      I think you make some good points Bob. I have noticed that women in our age range, at least the ones I know, want to be independent. I agree with the shady online photos–ugh. And I was guilty of not knowing what I wanted when I started dating. (I finally decided I didn’t want to date. I’d rather be my curmudgeonly self). But yes, if we could all treat each other compassionately as individuals…

  • Zee says:

    I just read the above observations and can’t help looking within. I ask myself would I identify with these women, after seven years of ‘widowing’ (thanks Debbie):
    1. Yes, I’m educated and have a serious career;
    2. No, I did not have an awful relationship with my beloved husband; he will always be a part of me so I am not trying to emotionally “get over” him;
    3. No, I never had to prove I can do it on my own – I always have; my husband took pride of my independent streak;
    4. We both did not want children (and I always get “so you don’t like kids” – I do like kids, I just don’t want the lifestyle of having kids) – no regrets & no worries, I have 8 siblings, 15+ nephews & nieces;
    5. I have six sisters and a handful of women friends but I also like my own company;
    6. I know what I want and the ‘kicker’ for me is the Happy Memories with my husband (the best lover, friend, partner … and I’m not idealizing) – this is why I did not rush with the dating thing. To quote Blythe Danner “when you’ve had the best why mess with the rest”.

    • Debbie says:

      Well said, Zee. Your late husband sounds like a wonderful guy. The above observations from the other commenter sounded like some of the women he met had unresolved issues about their prior relationships. I’m impressed by your independence…I’m working on that.

      • Bob H says:

        Please understand I’m a 53 year old Widow, single parent to a 9 year old, and I was giving my observations to my experience to on-line dating. I have commented a few time to this blog over the past year and I’ve given my real life experiences to surviving the sudden death of my wife while injecting some humor because life is hard enough. When I comment I’m tell the readers how life can be in my situation, moreover, I enjoy reading this blog because of all the heroic people out there that share their strength and wisdom to all of us.

  • Zee says:

    Hi Bob,
    I understand you’re sharing your real-life online dating experience and I do appreciate your honest observations, particularly as it is coming from a male perspective (as the topic at hand “5 reasons why older single women…” is from a female perspective). I merely applied my situation to your observations and I realized that it didn’t matter if one was in an awful or happy relationship, the prospect of dating is daunting.

    In the interest of sharing I had two really awful relationships before I met my husband. Our wonderful relationship didn’t magically happen. As I was coming from a bad experience I was determined to articulate what would or not work for me in a relationship, when we were still in the dating stage, and he as well. I think when we met we were at the point of our lives where we both listened and heard each other. We had 14 wondrous years together (his death was sudden, he died in his sleep; he was healthy).

    I wish you the best of luck in your journey and please do continue to share.


    • Debbie says:

      💙 to you both. It’s my blog, I get to comment. 😘

      • Bob H says:

        Zee, you are very fortunate to have had that time with your husband, my wife passed away almost exactly the same as your husband. To Debbie, it’s your blog and that’s why we love it so much!!!! 😉

  • Annie says:

    I was just taking a break from the social media work thing and decided to try a fun subject and voila! I found this fun read. Glad to see I am not alone! I have so given up on men (well mostly I guess and sadly) and that’s because I am c y n i c a l. I can’t be bothered to wade through the nonsense anymore. Here’s another thing – men my age do NOT appeal to me. Any other ladies have this problem? I see men who do but they are always a bit younger and never single. I do miss the companionship and sex drive not totally gone – well, not yet anyway. What’s a girl to do?

    • Debbie says:

      I too have that problem. And I know a couple of my girlfriends do too. We’re in pretty decent shape, and guys who’ve contacted us on dating sites are significantly older and seem much older, haven’t taken care of themselves, etc. One guy wearing moose antlers who sent a semi-sexy message is one of the reasons I went offline. You are not alone! I don’t have a solution except to wade through a lot of people and that’s a job in itself. (Sigh). Thanks for stopping by to read the blog!

      • Anne says:

        LOL. Still chuckling. Moose Antlers. Think I’ll start a group on FB where all us chikkies can share our experiences. Add some cartoons, could be quite funny. I don’t bother with online dating. I tried Badoo and the men were so repulsive, I was left chewing on my toes for a week—but no moose antlers.

        • Debbie says:

          If you do the group, add me! I have a blog page and I’ll friend you or whatever. Oh, the writing material! I might post more.

          • annie says:

            Hi Debbie, just created a group. Dames Dating Dilemmas on FB. Come along and join up (not sure how to add you) and get the ball rolling. Invite your friends. The group is closed so we can be as outrageous as we like (not too too rude though he he)

            Cheers Annie

          • Debbie says:

            Just asked to join. I’ll invite friends after I’ve gotten through more of my to do list! Awesome! Debbie

      • Therese says:

        I thought it was just me, but some of the men online seem so much older. My theory is that many people misrepresent their age online. It is a deal breaker for me. There are men in my age group (50’s) that are in great physical shape, but many want to date younger….go figure:) Something else I have noticed is that I receive messages from 20 and 30-somethings that want to connect. It is fun to email, but their motives are questionable.:)

        • Debbie says:

          No, it isn’t just you. Many men do seem to want to date younger. And people do change their ages so they’ll meet younger people. I did meet a few way younger guys who weren’t unethical or anything, but just wanted casual hook ups. (Not me).