Skip to main content

Dating in Your 50s and 60s: Online Dating, Expectations, and More

  • Author:
  • Updated date:

Shane is an observer of life and relationships, and is intrigued with the way we relate in our 50s and 60s.


No one ever thinks that at this stage in life that their marital status would read "Single." Whether it be from betrayal, drifting, death, mental issues, incompatibility or never finding the "one," life happens, and here we are... with more wisdom from all the birthdays. So now what?

What follows is simply some personal observations on dating in your 50s and 60s from my own journey.

  • Our Misled and Unrealistic Expectations
  • Our Own Online Avatar
  • The Rules Have Changed
  • Everyone Has Baggage From the Journey
  • Things Get Real Complicated, Real Quick
  • Our Adult Children
  • The Realities of Life
  • What Online Dating Does to Our Soul
  • Final Thoughts

Our Misled and Unrealistic Expectations

For whatever reason, finding yourself single in your 50s and 60s and then all of a sudden with the prospect of dating again can bring on a myriad of emotions and questions. These days, one in their 50s and 60s is left only with the desperate options of running into someone's cart at the grocery store, being introduced to a family friend at a dinner party, or even having to join a "Singles Group" at your Church or Synagogue to meet other singles.

For in these modern times, even with this age group, we have online dating in several flavors (Match, Bumble, eHarmony, OKCupid, etc.). Though we may be new to the "dating scene" after many years, at this point in the journey, we darn well know the kind of person we want and what we won't tolerate anymore.

But this is where we can become easily misled and develop expectations that are unrealistic. Online dating sites give us the impression that we get a "blank canvas" upon which to paint the person we have never experienced but always wanted, the person we now deserve after all the pain, heartache, abuse, and crap we have put up with through all the years. In this profile exercise (with enough time and paint), the temptation is to paint the perfect "one" for us. But upon more careful scrutiny of what we have painted, it becomes apparent that this is someone whom God has not yet created.

It doesn't take long before your thumb begins to cramp up from swiping left hundreds of times as you scour through photos and profiles of others' "Online avatar" . . . yet, we keep searching, holding onto the hope that "our" person is just a "swipe" away.

Our Own Online Avatar

From other venues of social media (Facebook, Instagram, etc), we are all familiar with the concept of creating our own "Online avatar." This is through the use of carefully selected photos, often with filters used that present us in the best of light and most times years younger. Then, with words, we project one who even in their 50s and 60s is fun, kind, full-of-life, well-traveled, well-read, loves kids, loves dogs, just an all-around blast to be around... and on-and-on the list goes.

The biggest drawback with the online avatars we create is that we will eventually have to show up in the flesh in all our glory (or lack thereof). It speaks volumes about this whole process when apparently the greatest compliment one can get when meeting someone in person and spending time together is, "You look just like your pictures!"

It is a natural temptation to present ourselves as something that doesn't mesh with the reality of our daily lives. Such is the nature of the online avatar. To post pictures of ourselves in exotic places, doing wild and fun things (even at our age) gives the impression that we are "full of life" and just a "party waiting to happen."

My Personal Example

I was communicating with someone who had presented and shared that she wanted a travel partner to see the remaining two continents and a handful of countries that she had yet to experience and explore. Yet, in further communications, her daily reality was she had moved to the city she was living in to help care for her grandchildren who had no father in their lives, her lease was up, and she had yet to find a job.

This is shared only to illustrate that the realities of our everyday human existence may not mesh with what we portray in our online avatar, or what we read about someone else. And navigating it all can be a slippery slope where our expectations need to be routinely assessed and tweaked in light of reality.

Everyone Has Baggage From the Journey

According to one study of adults using online dating in their 50s and 60s, the reality is that approximately 15% are "widowed", 5% have "never married", and close to 80% are "divorced."

Whatever category you find yourself in at this stage of life, we all have accumulated relational baggage from the realities of life's journey. We all have our baggage. Whether it's the loss of a spouse, enduring years of verbal and psychological abuse, lack of intimacy, decades of drifting, never feeling like you're enough, or whatever flavor the pain, we all develop ways of coping and relating that becomes baggage we carry and can become lenses through which we relate in the dating process. Viewing the whole dating process as two broken and baggaged persons simply walking together, getting to know and be known, can bring clarity, ease, and delight as you walk together.

Things Get Real Complicated, Real Quick

Unless both parties have "no children" or have "never been married," (more than rare in our 50s and 60s), the reality is that as you walk further down the relational path, "things can get real complicated, real quick."

One reason is that you both have years of life and experiences and relationships that have not only shaped you, but in most cases are still a vital part of your life (e.g., children and grandchildren). The further you walk down the relational path, the more people/relationships/experiences of your life will be shared.

With the sharing and the introduction of family members and friends comes a new level of expectation and complication that lay dormant when you were just "dating" and it was just "the two of you." But now there is the understood assumption that you will like them and they will like you... or at least that you will do whatever is necessary to win their approval and favor. If you thought meeting their parents and families decades ago was pressure and complicated things, just wait!

Our Adult Children

Most times, our adult children truly want the best for us. It is not unusual as you embark into the Dating World to hear something like, "Mom/Dad, we just want you to be happy!" And they DO... until they DON'T!

If you begin to walk with someone very far down the relational path, you might just hear something to the effect, "We want you to be happy, but just not with them." It doesn't really matter how old our grown children are or the cause of our 'singleness,' the idea of "mom/dad dating and having a boyfriend/girlfriend" oftentimes becomes too much. In some ways, it can be even more difficult for our adult children to accept and approve of what is playing out before them than for young children. And as stated previously, the further down the relational path you travel, the more complicated things can become.

If you feel burnt out from online dating, you can always take a break

If you feel burnt out from online dating, you can always take a break

The Realities of Life

As a Hospice Chaplain for several years, I have witnessed firsthand how this all ends. I am with couples/families on almost a daily basis who found each other later in life. That is all a wonderful thing, as it is often the first time they have experienced love.

All is well, but then one of them gets sick, and then, the grown children of the sick spouse swoop in to care for "their" parent, and it can quickly get complicated and messy beyond words. This sad scenario often ends with the parting of ways of the two families involved, as if the relationship their parents shared never happened. I have witnessed families wanting to erase the memory of it all to the point of not honoring the wishes of their deceased parent. Rather than being laid to rest next to the one who became the "Love of their Life," they had them buried in another cemetery.

What Online Dating Does to Our Soul

The entire process of online dating and keeping current with it all is exhausting, and oftentimes with nothing to show at the end of the day for all the work you've invested.

And then, play the game long enough, and all the searching, swiping, initial greetings, constant connecting with ongoing texting, phone call interviews, and first-time meet-ups take a toll on our souls. There is a swallow-ness of the soul that can begin to set in and can even become the lenses through which we see and relate to everyone around us. Our very sense of being human can become jaded as we so easily discard people with the simple motion of "swiping left."

Navigating dating apps and putting in all the work they require can be overwhelming and drain you emotionally, as well as take a toll on your soul. When you sense such feelings, back away. Take a break from it all and live life in the present, it will all be waiting for you when you return.

Final Thoughts

The above observations are just that, observations. The whole ordeal of dating in our 50s and 60s is a mix of good and not-so-good. We each have to navigate this often slippery slope the best we can, in light of our realities, availability, and resources of everyday life. There will be more forthcoming on the idea of finding Anam Cara in the midst of this search. But until then, enjoy the journey and those you meet along the way.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.