How to Date When You’re Over 50

Dating Tips for How to Date When You’re Over 50

Most men who are back in the dating world and have been “off the market” for a long time (usually, married) know that how to date when you’re over 50 can be intimidating.

If you’re divorced or your sweetheart died (sorry for your loss), you’ll have some different things to consider.

Either way, the dating scene has probably changed since you were last in it and you may have to update a few things to find success.

The other thing you need to consider is if you want to be with someone your own age or someone younger.

Should You Date a Younger Woman or Your Own Age?

There are pros and cons to both!

Younger women are usually more easy-going, playful and flexible. Older women have assets and can relate more in terms of life experience.

Younger women may want kids. Older women may have kids!

No matter what, women will expect you to be more bold and direct and all women will appreciate the same masculine traits:

  • brave
  • certain
  • leadership skills
  • decisive
  • stands for something
  • has self-interests (hobbies)
  • responsible
  • reliable
  • self-assured

Not too much to ask for, right? 😉

Other Consideriderations

Other things you’ll need to consider are if you’ll ever get married again; how merging mature lives with assets will work; children: yours and hers; and death and who gets what (inheritance).

Not very romantic, I know.

There are also practical tips you’ll need to know if you’re dating in your 50s like…

How dated is your style? Are you overdoing the cologne? Does that 23 year old really like you or your fat wallet? 😉

And where to meet women when you’re in your 50s is another consideration.

Aside from meeting women in “the real world” there’s online dating dating options, but be careful — not all sites and apps are created for the mature crowd.

One thing for sure is that there are more options for men in their 50s and love IS still possible for you (again).

Do you have any additional tips or thoughts on how to date when you’re over 50? Let me know in the comments!

xo AJ

p.s. I think I’m addicted to key lime pie. This has zero relevance to this post, I know.

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I am not a professional psychologist or licensed therapist. You’re responsible for yourself. Obey the law.

About the Author Anna Jorgensen

Vancouver dating coach for men who love women! ❤️ (Not PC and not a feminist.)

Leave a Comment:

Andreas says January 1, 2020

Great post/video. I am in the +50 category (divorced) and have come the same conclusions. Age-matched dating (8-12 yrs difference) is very different from age-difference dating and a completely different experience when it comes to the actual dating event. Agree with all of your assessment on the women’s focus when the age difference is > 15 years. They are in a different stage of their life and are looking for something different.

There is another interesting topic in that regard that I hope you could comment on. If you divide the pool of available women for +50 men into 2 categories you have younger and older, but also the ones that have been married or in committed relationship and the ones who have not been married. Could you comment on the difference in dating women from the last category? I would very much appreciate it. Thanks!

P.S. Key lime pie addictions are hard to fight. Good luck with that.

    Anna Jorgensen says January 2, 2020

    Thanks for watching my videos, reading my blog and commenting! This is a bigger topic than a comment reply can address but I’ll give you the Cliff/Coles Notes…
    Women who’d experienced long term relationships usually know how to do a long term relationship, even if it failed. They may or may not have taken responsibility for their share in the relationship’s failure, however. Good question to ask them, What was your part in the relationship not succeeding? — This will tell you a lot about her accountability or lack thereof.
    Women who haven’t been in a LTR are either not very dateable (too bitter, shy, ugly, emotionally damaged etc) or very picky, watch out for the latter, you’ll never measure up to her impossible standards. The former has potential if she doesn’t have ALL those nasty qualities.
    Obviously, there are many exceptions to this off-the-cuff reply and nuances as well. Cheers. Anna

      Andreas Huhmer says January 2, 2020

      Thanks for the answer. Makes sense. Still would love you to do a video on it. Particularly, how you find out about those relationship detractors. A lot of guys would want to know.

        Anna Jorgensen says January 3, 2020

        Noted 🙂

Andreas Huhmer says January 2, 2020

Bought your book. Reading through the first chapter and I am in tears.

    Anna Jorgensen says January 3, 2020

    You have a tender, compassionate heart. I’m really ok now! I think I had to go through all that to be able to help hurting people. 🙂

Barry says January 8, 2020

Not sure whether you saw my message on fb.
I’m 5’5, 50,130 pounds
Had tons of first dates from dating apps but hardly any second dates, I have a problem with my right eye called nystagmus…. could that be a major factor in my inability to achieve multiple dates with one woman? I know the height is an issue too. I have 7 yr old twin boys that don’t live with me but I c them often.
I think I’ve had over 100 dates In the past 3 years with maybe 5 second dates.
I don’t smell bad or lie about my looks so I’m not sure what the problem is —- though I am an introvert there are usually no awkward silences in conversation

David Hinchliffe says January 10, 2020

Hi Anna,

Sorry I am not up on a lot of the lingo people use as well as the short hand one letter words people have used in their comments.
In this video you use the word Betta (not even sure if I spelled it right). I have never heard this before. Does it mean better?

Thank You

    Anna Jorgensen says January 13, 2020

    Hi David,
    In a nutshell, well, it’s kind of all about the nuts — or rather, where a man keeps them. Alpha = dominant / masculine male. Beta = submissive / feminine male. If a man keeps his nuts in a woman’s purse, he’s a beta male. Meaning, she calls the shots. Basically.
    Dominant women tend to be attracted to submissive men (or they try to make a dominant man submissive, but it doesn’t work).
    Make sense?

      David Hinchliffe says January 14, 2020

      Thank You Anna. I understand. I just never heard it pronounced that way before.

Kenneth Vincent says January 24, 2020

I am 69 years old single Male who is looking for companionship. Yes I occasionally take a female to dinner. However have not found the right person for a a long term relationship.

Richard England says January 27, 2020

Ana love your videos, makes me think!

Ken Flanigan says January 28, 2020

Dear Anna,

You are a delight and so refreshing! Thank you for your contributions.

My best to you,


Robert Malloy says April 7, 2020

Ms. Wingman, you are a Frigin’ HOTTIE! I Love the way you portray and put your point on the subject matter for us “Dicks” to understand, take in and absorb. Your sense of humour is a “hoot”. which makes a rather threatening subject of dating again…”Getting back in the saddle again” so to speak! I was listening to Stephanie Lyn life coach. While learning a lot about narcissistic women etc. I find your approach more raw and to the point of the topic and getting through to this sometimes “Thick-Headed” guy. And I’m not revering to ‘down south’ Ha! (oh…I am handsome. charming and have a whole lot of Love to give) Yeah. I think that’s three. I am practicing. after 40 F’n years being married to a narcissist, I find myself fully damaged. but am being healed by what your videos are doing for my inner man. I especially admire your belief system and not afraid to put it out there. Without God in my life and the power of prayer in my life…I’d be a goner. He Gawn! Ha! Keep up the good work…It works if you work it, and I/you are worth it!!! Yeah, I know cheesy! Something I picked up at ’12 step. meetings. Stay safe and healthy Ms. A.J.

    Anna Jorgensen says April 7, 2020

    Thank you so much for reading and commenting! God bless you! 🙂

Robert says April 7, 2020

I commented in great length in my last comment. tells me “my comment is awaiting moderation'” keep up the Great work you’re doing. you are making a whole lot of sense to this “Dick”! Ha!

    Anna Jorgensen says April 7, 2020

    All of us, whether chicks or dicks, have a lot to learn about love! 🙂

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