6 Hot Tips for Dating Over 50

Age is just a number. If you’re 60, I assume you feel 50. If you’re 50, I assume you feel 40, and so on. But when it comes to dating – specifically online dating – age isn’t just a number. It’s a real thing that you have to contend with, an obstacle that needs to be overcome. So what do you do when the dating pool gets smaller and, arguably, worse on the far side of 50? Stick around and I’ll tell you exactly what to do.

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  1. 1

    Ty Evan, I noticed you laughed today when you said grandpa…I had previously posted on another one of your blogs about GRANDPA MUENSTER & HIS…PEN15–HOW HE WROTE ME A DETAILED LETTER ABOUT IT (AT AGE 86) etc.

    I also told you about the LEPRECHAUN (no not magically delicious)–well he recently showed up in one of my meetup groups (I did not attend that one) & I clued in the organizer…her observations were the same as mine!

    Since that post I made, a younger man who I suspect is looking for a sugar mama asked me to dinner, I declined.

    Once again, I am working on me (losing the covid 20) & will put myself on a quality pay site in the spring, when it is safer.

    Thank you for including us older gals in your discussion!

  2. 2

    Agree Evan! You have to understand the medium of online dating and be savvy how to make it work for you. Like the option women selecting those men that have included their specifics in the profile they are looking for. The “order up/menu style” of filters, and selection, to your point could eliminate a lot of really good matches and creates a false expectation that will not be met. Selecting certain age ranges (yes, men select younger but so do women), body types, etc. can artificially weed out very good matches. Agree that age is only really critical if you want children. But I also think people need to be mindful of those filters and not waste their time if someone has specific preferences (no, they won’t change their mind because you have “other special qualities). I think too many people are not realistic on dating sites and don’t know how to use them (ie the old geezers hitting up the 25 something because it’s “worth a shot). The other thing women need to be mindful is that personal appearance and fitness is important. Yes, a few extra pounds and gray hair is not a sin, but it also narrows your dating pool to suitors that are more relaxed about those things (because they are gray and have a few extra points too). Personal brand matters; looks, fitness, confidence matters. And not taking care of yourself limits your choices. It’s not shallow, it’s human nature. I am in my mid 50’s and date younger because most people guess I’m in my early 40’s. I work very hard at it. And it gives me more choices than some of my peers who look like they could be my mother. It’s about being realistic and leveraging online tools, and your personal brand for the best turnout. There are men out there for you, you have to be strategic about finding them. And realistic about your choices.

  3. 3

    “And it gives me more choices than some of my peers who look like they could be my mother. It’s about being realistic and leveraging online tools, and your personal brand for the best turnout. There are men out there for you, you have to be strategic about finding them. And realistic about your choices.”

    So on point!

    My experience has been I attract men way more successfully IRL because I look like I could be my own daughter ;0P Online, if I list my real age,the IRL men who check me out may not be looking there…

    And I am not interested in “men” rather one man only–I found that mindset attracts a like minded man—Am I out there to win a popularity contest & stroke my ego,or am I looking to connect w/one man for an emotionally & physically intimate relationship?

    When I was on “Old Man Time” it was exhausting because I had to weed through 1,000 messages to start conversing w/10 who had some potential–I’d rather be on a site where I start off conversing w/ 10 men & quickly whittle it down to 1

    When the pandemic calms down, I will put myself on a higher quality pay site & follow your advice, Evan!

  4. 4

    Popped in to hear what Mark had to say on the topic and then did a reverse search on Match. Was surprised to see that the people who were looking for people like me were NOT the people that I was looking for. I then did a mutual match search, which returned just a handful of the type of person I was seeking. The people I was most interested in? Even men that were 10 years older were NOT popping up in my mutual or reverse searches.

    Just as EMC and others have said, when I go out in real life, I get asked out frequently, and many of the people who ask me out are much younger because I do not look my age.

    So is age just a number? Yes. Except when we are shopping for humans and view our options like rows of salad dressing on a supermarket shelf. I imagine a man’s search might look like this… (Just guessing here)…
    – Race
    – Distance
    – Attractiveness
    – Physique
    – Fitness level
    – Interests
    – Religion (maybe)
    – Education
    – Political affiliation
    – Age range

    If I check every single one of those boxes, and we are both not interested in having children, does me being five years outside of your age range really make that much of a difference? I get that we can only control our own actions and behaviors. I get that I’m spinning my wheels by fretting that I’m being overlooked because of my age. But I still can’t help but feeling sad that a great match could be passing up a great match like me, just because of my age.

    I try and think positively, so I’m going to flip back to my optimistic self. The good news is that I went to three weddings last year, and two of the ladies were over 50 and married a man that they met online. I just got news of two more acquaintances that got engaged in 2020. One woman is 51 and the other is in her late 50’s. It’s possible. I don’t think it’s easy, but it is possible.

    Let’s keep the faith, ladies.

  5. 5

    Jeanne, thank you for getting it. It’s not about judging but it is about being realistic and knowing the medium you are participating in. And understanding your own marketability and choosing accordingly. Pain comes from not aligning those two things.

  6. 6
    Yet Another Guy

    I spent two years on the dating sites as part of the top 20% of men within my cohort; therefore, I believe that I am qualified to speak on the subject. I believe that a major problem women have over age fifty is accepting that the men who contact them on a dating site establish their sexual market value (SMV). If the men who are contacting a woman are not the men she wants, then she needs to do a complete makeover, including cosmetic surgery if necessary, or accept that her perceived SMV is higher than her actual SMV and adjust her desires until they align with her actual SMV. Older Men do not care about a peer-age woman’s status or how much she earns. Those attributes do not add to a woman’s SMV like do a man’s because men do not expect a woman to earn more than they do.

    As far as to the “I look younger than I am” comment, well, ladies, I hate to burst your bubble. There are a lot of women like you who are taking liberties with their claimed age on dating sites. They may look younger in a peer-age browse, but rest assured, they do not look like women ten years their junior in a browse of women who are actually ten years younger. Within every age cohort, there are younger looking, age appropriate looking, and older looking members because people age at different rates. For example, I will be sixty next year, have most of my hair, and it is still at least 99% its natural color (i.e., I have very little gray). I still have enough hair volume that I can rock the undercut hair style plus stubble look that is popular with younger men today and not look like a caricature. That being said, I may look good for my age, but I would not dare shave ten years off of my chronological on a dating site even though I was routinely challenged as to the age of my photos which were current.

    Sadly, there are still quite a few delusional older men who believe that their money entitles them to a much younger woman, it does not. However, that is a story for another day. What matters today is that the top 20% of older men (i.e., men age 50 and older) have so many options that getting a member of this group to settle into a relationship takes an amazing woman coupled with great sex and perfect timing. Even then, members of this group generally have no desire to remarry. I have been with my girlfriend for over two years and have cohabitated with her for a year. I still have no desire to remarry and my girlfriend is easily the best woman with whom I have ever shared my life. After man has his family, there is nothing in it for him to remarry. Men do not fear dying alone. Men fear dying broke.

    With that said, I remember what Jeanne wrote when Buck25 mentioned that he wanted to know if a woman was still interested in sex. She wrote that sex is not important to men her age. I was like, “keep that delusion alive, sister.” Well, sex is still very important to me. I would assert that any man who does not date with the immediate goal of finding a woman who is fun and with whom he can have sex is impotent. Sex is what drives men to date, period, end of story. Men do not join dating sites with the goal of establishing a long-term relationship (LTR). An LTR for most men is a side-effect of finding a woman who is more fun to be with than other women and with whom the sex is good. Why? Because a) a man’s most basic primal need to procreate the species, even if he is past normal parenting age, and b) men are not the gatekeepers of sex. Men are the gatekeepers to commitment, which they use to obtain sex.

  7. 7

    YAG, you wrote, “After man has his family, there is nothing in it for him to remarry. Men do not fear dying alone.” This is so wrong, I couldn’t let it alone. Male depression sky-rockets when men are alone. Male ill-health sky-rockets. Suicide rates sky-rocket. Listlessness sky-rockets. The largest predictor of male happiness and health is love and relationships. To say that men (and particularly older men!) have nothing in it to remarry is absolute clap-trap nonsense. Some men are avoidant. Their fears and insecurities colour their relationships, and they extrapolate incorrectly onto others. That….happens.

    1. 7.1
      Evan Marc Katz

      As usual, plenty of truth buried in a simplistic message that turns all women into SMV whose value is regular sex and men into independent warriors who don’t value love and commitment. You may be speaking for yourself, YAG, which is fine, but don’t think for a second you speak for all (or even most) men.

  8. 8
    In Hiding

    And just when YAG had talked me into giving up…..

  9. 9
    Yet Another Guy


    What I saw when I was in the dating pool was that divorced men in my age group who were in the top 20% had no incentive whatsoever to settle into an LTR. Why would they? Online dating has made it such that a single man who is in the top 20% has absolutely no reason to pick just one woman, and if a woman manages to snag one of these men, she can pretty much be assured that he is keeping his options open, that is, unless she is in the top 20% of women. We can blame that mentality on a character flaw or we can acknowledge the fact that 80% of the women on dating sites focus their attention on the top 20% of men on dating sites.

    As far as to the ladies who claim that they do better in person, well, online dating is a crucible. Yes, women get overlooked for their age, but not hot women. Hot women of all ages have absolutely no problem getting dates on dating sites, even with younger men. It is the women who have an elevated sense of their SMV who do not get it. How many times has a guy shorter than 5’10” complained about being filtered out based on his height on this blog? These men use the same “I do better in person” argument, which I believe. Once again, online dating is a harsh reality for those who are not in touch with who they can attract based solely on their on-paper attributes and their photos. A woman who is only considering men who are well-educated, well-kempt, successful, taller than average, fit, and attractive needs to get in line because she is not only competing with her peers, she is competing with younger woman, often much younger women.

    As far as to older divorced men fearing dying broke more than fearing dying alone, well, that has been my experience when interacting with older divorced men in many different social settings. I would agree that the loner-type divorced older man may fear dying alone more than dying broke. However, I have many peer-age divorced male friends who have no interest in being in a relationship ever again. In their words, the juice is not worth the squeeze. These men do not hate women. They just do not want to provision another woman or risk having to split their assets again. They also have one thing in common; namely, they live rich lives, which involve their children and socializing with friends and family on a regular basis. There are a lot of older divorced women who do the same thing.

  10. 10
    In Hiding


    What is your ultimate goal here? Are trying to discourage women and make us feel horrible about ourselves because we don’t live up to your hotness expectations? I’m sure you think you’re helping but all you’re accomplishing with this is telling women they can’t trust any man and the just need to settle for the guy with no job, no car, and no teeth. Nothing you said here gives any hope or encouragement.

  11. 11
    Emily to

    “What I saw when I was in the dating pool was that divorced men in my age group who were in the top 20% had no incentive whatsoever to settle into an LTR. Why would they?”
    You are missing the point. I’m sure some men get tired of casual relationships. It is like having a bunch of casual friends who don’t really know you.

  12. 12

    Inasmuch as a full head of (mostly) non-gray hair is a flawless guarantor of intelligence, integrity, kindness and empathy, we can all be 100% sure that YAG’s girlfriend is a very, very lucky woman.

  13. 13

    Curious if other 50+ women experience this nuance of the few-good-men issue: boring men.

    So many 50+ men (and maybe women, too, but I don’t date them) seem ready to simply float into retirement and are pretty much done striving toward new goals. If the recent election has shown us nothing else, it is possible to make significant accomplishments in your 70s; your 50s and 60s are way too young to just give up.

  14. 14
    Yet Another Guy


    First off, by goals, do you mean professional goals? If so, do you love your career/job? A lot of men and women are exhausted from careers that they have come to despise. Work becomes a grind when one despises his/her career choice, especially after age 50. I am willing to bet that many of the 50+ men who appear so ready to float into retirement have sacrificed much professionally in order to secure a better retirement. These men are not thinking about future goals. They are focused on the financial freedom to do absolutely nothing that retirement will bring to their lives.

  15. 15

    I mean *any* goals. Physical fitness goals, travel goals, volunteering goals…and I don’t necessarily mean anything dramatic, I’m not talking do an Ironman or climb Everest. In expanding my thought, I guess what I’m griping about is how it is soooo common to hear people say how they look so young for their age. But – as always, just in my own experience – men I meet act exactly their age, or older. What I miss about being young isn’t skin tone or silver-free hair, it is being around peer-age people who have sparkling dreams about the future. I don’t want to give that up.

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