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Challenges Of Relearning How To Date – Part 3

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by Amy Jones

When I first began writing this article, I knew it was going to be long. However, the more I think about all the dating challenges for people post divorce and over 50, the more it grew.  You may, like me, have experienced one or more of these challenges or others. In the final part of this 3-part series, I will discuss some of the interesting questions I’ve been asked. Shared experiences always help us realize we aren’t the only ones going through awkward encounters!

To recap the dating challenges from the prior 2 articles:

  • The first challenge is how guarded people have become.
  • The second challenge is communication style.
  • The third challenge is pressure to only date one person.
  • The fourth challenge is appropriate dates.
  • The fifth challenge is being vulnerable.
  • The sixth challenge is appearance and self-pride.
  • The seventh challenge is who pays?
  • The eighth challenge is the big one: SEX.


    Challenges of Relearning How to Date Part 1
    Challenges of Relearning How to Date Part 2

The remaining challenges come in the form of questions:

Why are you still single?

dating challengesThis is always an interesting question – like there is something wrong with being single (I mean I don’t have any visible deficiencies…). I needed time to heal from my 14 year marriage and learn from my experiences. I didn’t want to bring any unhealthy or out of balance personality drama into a relationship (sound familiar?).  I took time to focus on myself, figure out what I needed and wanted.  I’m not going to compromise, and I don’t think anyone else should either. I’m single because I haven’t found the right feeling, fit or connection. There’s not anything wrong with me, I just haven’t found the right man.

Why don’t you have a relationship with your ex?

I came out of a very draining and stressful relationship. I don’t want to put that negative energy on anyone else and, honestly, I don’t think its good to have a relationship with ANY ex unless you are co-parenting.  It can be a little awkward and feel kind of like a third wheel for some. Why put that feeling on anyone? And, does it really matter if I have a relationship with my ex or not?

What are you looking for in a man or next relationship?

I am looking for a feeling of contentment, comfort, protection and consistency. Isn’t that what all women want? I think men want this too…it’s important to feel like we can be ourselves in a relationship. All the superficial stuff fades with time and age but the feeling never does. For me, it’s important to be in the moment of how someone makes me feel vs. analyzing what’s going on. I learned this important lesson from my married friends.

Why/how did you last relationship end?

Without going into detail, I caught the last man I dated in a really BIG lie. In some way, I feel like it was my fault that I didn’t see it coming. I had some taps on my shoulder that the relationship wasn’t quite right, but I’m a very understanding person and think that everyone deserves a fair chance. Part of the problem was my fault for not seeing things clearly; however the responsibility lies with him for not being honest with me. But…I was an active participant in allowing the relationship to continue when I should have ended it. I’m embarrassed that I allowed it to continue longer than I should have.

Do you want to get married again?

This is the hardest question for me. I used to think the answer was yes, but the older I get, the more I think about what being married means vs. being in a committed, long term relationship. Maybe it’s a little bit of the Susan Sarandon in me that makes me think about her long-term relationship with Tim Robbins. I always admired their commitment and obvious affection for each other. She marched/marches to the beat of her own drum and I respect that. So, the answer is always, “I’m not sure. It will depend on the person, the situation and the timing.”

The bottom line:

There are probably many other questions you’ve been asked over time and some you get over and over again.  Hearing and answering the same questions is exhausting. I try to remember each person deserves a first and fair chance without preconceived notions about “what is” or “what isn’t”. The older we get, the more challenges we may have. The longer we are alone, the more accustomed we become to being single. We get set in our ways and merging lives and lifestyles can be challenging. Though compromise is sometimes difficult, for me, the rewards far outweigh the thought of remaining single the rest of my life.

Life experiences make it hard to come to the table with an empty slate. We all have baggage and as my therapist used to say, “You have to find someone who will not only help you carry your baggage but will also help you unpack it.” As travelers along this journey called life, we bring our past experiences with us; baggage can be light or heavy depending upon self-reflection, healing and progress we’ve accomplished.

I believe life is enhanced when shared, especially shared experiences, shared lives and shared love. My focus is to continue my search for that one person who will not pose challenges but will offer something significant, consistent and comfortable. What about you?


Challenges of Relearning How to Date Part 1
Challenges of Relearning How to Date Part 2


Amy Jones

Amy Jones

Amy is a personal growth visionary, international speaker and author who lives and breathes one simple philosophy:  live in the moment. For over two decades, she has inspired thousands of people; intent on helping facilitate their personal growth and self-healing process by creating opportunities for significant and lasting life changes through personal interactions, workshops and writing found on

Amy is a highly sought-after speaker and her series Getting Rid of Possessions:  It’s Harder Than You Think has the highest attendance in the history of the Generations program at Methodist Health Systems. She is the author of Better for Being Broken and co-author of Break Through with Johnny Wimbrey, Nik Halik and Les Brown.

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