Midlife Dating: What Really Matters

a woman sitting alone on a cliff

To Thine Own Self Be True

In some ways, midlife is a time of enlightenment. Sounds grand, even romantic, doesn’t it? But really, I have developed insight and wisdom over the past ten+ years in a number of ways, including dating. All thanks to my winding, crooked, detour-laden path. I once read experience is what you get when you don’t get what you want

Dating is one of the areas where I’ve had my share of opportunities for growth (don’t you love my positive perspective). My trial and error through relationships has taught me the importance of mastering four key elements of self before taking another step forward in the dating arena.



According to Google Dictionary self-awareness is defined as a conscious knowledge of one’s own character, feelings, motives, and desires.  Because of my journey, I am much more cognizant of who I am, my wants and needs, and equally, what I won’t settle for. This includes self-validation of my likes, dislikes, interests, talents, strengths, weaknesses, emotions, and passions. Developing intrapersonal skills is a must when it comes to healthy relationships.

Being self-aware also encompasses interpersonal skills, including the ability to understand other people, how they in turn perceive you, and the best way to interact with one compared to another. Work on any areas you feel need improvement, and then own your stuff with no excuses or attempts to change for anyone. This leads to self-confidence.

A woman stands on top of a tall cliff and praises


We develop self-confidence when we are able to master different pursuits and skills, including the art of healthy relationships. Vulnerability comes into play here.  I open my heart to the possibility of hurt and failure to have a chance at love. Read our post on vulnerability here.

My belief in myself has grown tremendously through trial and error, continuing to put one foot in front of the other. Managing to get back up when I stumble and fall. This eventually builds self-confidence and efficacy.

When it comes to dating, I no longer try to impress anyone or be someone other than who I am. Having confidence in ourselves leads to wisdom.




I am a fan of Deepak Chopra. In his book The 7 Laws of Spiritual Success he discusses the power of acceptance and letting go. Wisdom is accepting what is, even though we may want things to be different right this very moment. The next step is letting go of the desire to control the outcome. True abandonment comes when we allow the universal order to unfold and create whatever is meant to be.  Wisdom is backing up, releasing, and practicing gratitude for what transpires, even if it isn’t what you hoped for.


A woman reads a book alone before a night sky.


At this point it is time to get focused.  I read an article many years ago about how to manifest the love or your life. It recommended making a Love List—an inventory of 100 characteristics you expect and need in another person for them to be considered relationship material.

I agree–100 items is a bit daunting. I admit a few are a bit trivial, like eye color or the vehicle they drive. But focused it is!

I am seeking someone who is intelligent, kind, and respectful. He needs to be adventurous, fun and can easily make me laugh. He loves animals, nature, and deep conversation over a cup of hot coffee early in the morning.  See, only 91 more to go!




Create your list and use it to rate a potential partner after spending a decent amount of time together. Determine the minimum score needed to earn a passing grade. Now, put this new person to the test. True or false– do they exhibit the trait or not? Overall do they pass the test? No? Move on if your quest is for a long-term relationship.

I decided to approach dating as an adventure–who knows, perhaps I will write a book on midlife dating some day.

Read out post  Online Dating in Midlife: Help is Here!

I would love to hear your perspective on dating in midlife– please share in the comments below!

Till next time, Sandra


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11 thoughts on “Midlife Dating: What Really Matters

  • October 18, 2017 at 1:23 pm

    I love your perspective on dating!! Especially not changing anything about yourself 🙂 I’m only 22 so not midlife yet but I still found a lot of this applies! I just got out of a 2.5 year relationship so I’m totally new to the game. Taking your advice to heart <3

    • October 18, 2017 at 1:44 pm

      Always believe in yourself!
      Thanks Julia!

  • October 19, 2017 at 11:33 am

    wow this is very eye opening, am not there yet but I like to be informed. Great read

    • October 19, 2017 at 11:47 am

      I think it is great you are taking your time and not jumping in! It is healthy to learn to be okay with being single!

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  • October 24, 2017 at 2:15 am

    These are some great points. You definitely have to be confident in who you are, and have some sense of an idea of what you’re wanting out of the relationship. I feel like when we are younger, we are dating around merely trying to fill some sort of “void” in our life. However, when we have had time to mature, we gain the confidence needed to fill these voids on our own, and become mentally stronger, more independent, and don’t “need” to be in a relationship, but “want” to. There is a big difference, and this difference will also determine the path the relationship can take.

    Another thing I have learned from the hardships of dating, is that it will not work out if that persons happiness does not mean more than your own.

    • October 24, 2017 at 12:47 pm


      Experience really is a great teacher if we choose to learn the lessons presented to us!


  • Pingback: Coming Face to Face with Vulnerability ~ Boom2Bloom.com

  • December 13, 2017 at 4:40 am

    Honestly, just read three of your articles and found them so refreshing. I look at everything in a positive light, except myself sometimes. I’m working on that. I may start my 100 list while waiting for personal enlightenment 😊. I don’t know many (3 maybe) women my age that are in my boat. So, thank you!! I’m glad social media led me to you and your writing. Your positive outlook is catchy!

    • December 13, 2017 at 12:25 pm

      Thank you–take a look in the mirror, though. Your posts have the same effect!
      Keep doing beautiful things!


  • Pingback: Midlife Intimacy: It Really is Important! ~ Boom2Bloom.com

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