The Unexpected Similarities Between Dating in Your 20’s and Dating in Your 50’s

The Unexpected Similarities Between Dating in Your 20's and Dating in Your 50's

The dating world has recently been piquing my interest. No, my relationship isn’t in turmoil, quite the opposite actually. It’s just that having people around me in the dating world is making me evermore curious to see that though the circumstances may be different when dating in your 50’s there are so many similarities to the days when I used to make the rounds in the dating scene. Believe me, dating wasn’t an aspect of my 20’s that I particularly liked, nor do I miss it. I have learnt a lot of lessons from my time spent in the world of dating, and it seems to me that even though dating in your 50’s is still very different from dating in your 20’s (goodbye to the tick-tock of the biological clock), it can prove to be just as tough. Even though the circumstances of dating in your 20’s and your 50’s can be day and night, there are still some very important things to remember no matter what your age. If you’re casually dating it’d be wise to heed my advice.

The Unexpected Similarities Between Dating in Your 20’s and Dating in Your 50’s

The Need to Practice Safe Sex

If you were/are in your 20’s and casually dating, chances are that “practice safe sex” was at the top of your dating priorities. That should’t change for 50 year old’s, and practicing safe sex should still be at the top of the list. While the reasons tend to be entirely different, practicing safe sex is always a good idea at any age, but especially if you are immersed in the dating scene and are casually dating. In your 20’s your priority was to not get pregnant (probably tied with don’t get an STD) and you may not think that the entire safe sex agenda also applies to you in your 50’s. Think again. Cases of HIV and STD’s are on the rise with the over 50’s due to the promiscuity and renaissance this age group is experiencing in the casual dating scene.

The Need for Your Personal Space

Fun fact, I’ve only lived with one man. Although, I don’t think this is the norm, I do find that it helped me tremendously as I was navigating not only my dating life, but also getting to know myself more as an adult and solidifying who it is I was. As it happens in your 20’s the excitement of a new lover can sweep you off your feet, but you needn’t let it carry you away. In your 20’s it is wise to not live with your partner initially as it helps you grow in your relationship and grow as an individual without feeling suffocated or having another persons daily needs hinder your own. In your 50’s you are probably used to living in your own home, either having lived on your own for a long time or even a few years. You know your likes, dislikes, and there’s something about someone else disrupting your routine and personal space that can quickly make living together go from romantic gesture to unavoidable annoyance.

The Insecurities

Will this go anywhere? Should I call him first? Does this dress make me look fat? Whether you are in your 20’s or your 50’s I hear dating insecurities that almost mirror each other from each side of the spectrum. My 20 something friends are dealing with whether or not it’s a power move to call him out if he’s being distant, whilst my 50 something family members are dealing with whether or not they should speak up for themselves and their feelings if he is being distant. The commonality is that some of these women aren’t sure of themselves and what it is they are willing to accept from a partner. Whether they have been dating for 10 years without finding the man they’ll marry, or they’ve done the whole marriage thing already and the prospect of starting over makes them vulnerable, we all tend to have the same insecurities despite our age.

All in all we aren’t so different. Even though with age comes experience and that experience brings wisdom, it’s not always what one expects it to be. The dating game is called the dating game for a reason, and the best way to make it work for you is to play your cards right, have fun, and at least in the sense of enjoying it, playing it as a game.

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The Unexpected Similarities Between Dating in Your 20's and Dating in Your 50's


  • Gareth Torrance

    I think things like insecurities aren’t actually affected by age. And to be honest, I don’t think age really changes dating that much either, except that maybe you are more mature and think about who you are dating more…

  • Nelu

    I’m 20 myself and it’s easy to think that older people just don’t have insecurities. I’m glad to know the truth. Thanks!

  • I think the need for personal space is important at any age and whether you’re in a relationship or single. I definitely never thought about ppl in their 50’s dealing with insecurities, but I guess insecurities never really go away.

  • Natasha Mairs

    I have never really been on a date. I first met my husband when I was 12, and we started going out together when I was 18. I am now 32 and we are still going strong

  • I think the need to have your own space and grow as individual people is so important regardless of your age x

  • Becca Talbot

    Interesting that the number of cases of HIV and STDs in the over 50s is on the rise – I wonder if there’s a correlation between that an the increasing number of dating sites like Tinder etc, which are allowing the over 50s to find new partners more readily? Food for thought x

  • Jennifer Eastwell

    Personal space is so important in my opinion in relationships. You need time for yourself and time with your friends. You don’t have to do everything together. My partner and I have been together for almost 4 years and we have a very good relationship 🙂 we don’t mind if we want to do things separately!

  • I’ve never really given it much thought really… mainly because I’ve never actually ‘dated’. I met my fella when we were 15 and we’ve been together for 10 years. Teenage sweethearts. I think I’d crumble if I had to experience the dating world. It sounds awful.

  • I haven’t dated in many years but one thing I know is that I love my own space. My own time to think and be alone, its for me a very healthy thing. X

  • Lauretta

    I agree, 20s or 50s, let’s play our cards right. Give your self a personal time to contemplate what’s best for you.

  • Angela Milnes

    This is so so interesting. I dated at 16 and in my early 20’s and then in my 30’s and it’s always the same!

  • Hungry_Healthy_Happy

    I have never dated, but I can see how it would always be similar. It looks tough!

  • I have just stopped dating someone and found myself saying yes to so many of these things!

  • Love this, even for me. Dating really hasn’t changed much from when I was a teenage to now being in my 30’s x

  • Baby Isabella

    My grandma started dating in her 50’s and found the experience very strange, thankfully she met someone very quickly and they are in a happy relationship, but it was mostly online before they met which she wasn’t used too!

  • Kira L Curtis

    Really interesting to think about it like this! Can’t say I’ve ever really dated so I don’t know what it’s like so it’s interesting to think about it being the same basically at all ages!

  • Leah Shafik

    I don’t think it really changes throughout any age. Yes the location and the event might change but everything else will be the same.

  • FussFreeJen

    I’ve had the dating experience through a few of my own stages in my 44 years. And I must for me, it was easier as I got older. I felt a little more sensible, probably because I knew better of what I wanted. Although still experienced the fails, it just got a bit easier and I wasn’t taken for the fool.

  • Jessica Lynn Martin

    I have a great aunt who is 80 and she has been dating over the past 5 years. When she described to me what dating was like for her, I couldn’t help but think how similar it was to my experience as a 20 year old. You have pinpointed these similarities because they are the exact ones my great aunt told me about it.

  • for me, personal space is a big thing for me. i can’t imagine myself being with that one person 24/7

  • This was a really important topic for you to address. You should practice safe sex at any age but like you said the ‘renaissance period’ can lead to a lot of casual hookups without thoughts of the consequences. I like to stay protected.

  • Ayesha Farhad

    I’ve been married for a good 6 years so haven’t been out in the field since so long! but I kinda feel that in your 20s you dont need as much personal space than in your 50s. You’ve lived half your life with ups and downs and your have your own personal space territory. Like there are VERY very few things in your 50s that you would rather do it yourself than with someone else as opposed to in your 20s.

  • Evelina Vilke

    What an interesting post! I guess the main challenges stay the same no matter what age you are