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Challenges of Relearning How to Date: Part 1

challenges post divorce dating

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Author: Amy Jones

If you haven’t noticed, dating is quite different now in this technology driven, fast paced, instant gratification post-divorce world.

There are numerous divorced singles; for those of us who want to find love and get married again, we are on a search. You would think living in a highly populated area with numerous divorced singles that the search would be easier. There are multiple online dating sites, scores of restaurants, bars, social activities and volunteer opportunities. Any type of class you want to take is also an opportunity to meet people; yoga, dance, foreign language, golf, tennis, etc. There are activities specifically geared toward singles. So, what is happening? Why it is so hard to meet people?

I’ve been divorced for almost nine years. In that time, I’ve had two short term relationships lasting less than eight months and one long term relationship that lasted almost two years. In one of the relationships, we were introduced by mutual friends. The other two relationships were through meeting online. As I stated in my last article, Stop Missing This Important Aspect Of Successful Dating At 50+, I am no longer dating online. I recognized over time that it was really difficult to make a connection in a virtual world and it was taking a lot of effort with little at 50plus

I realize going back to the basics of seeing, connecting and meeting a man in person may take longer.  

However, I am willing to invest the time, energy and effort I know it will take to create a quality experience and connection. I also recognize I am going to have to relearn how to date. So, I contemplated the experiences I’ve had over time and reviewed what has worked and what hasn’t worked in the time I’ve been single. I came up quite a few challenges. The following is part one of a three-part article.

The first challenge is how guarded people have become.

I recognize each of us have our own marriage, divorce and post-divorce story. After being divorced for almost 9 years, you can just imagine how many stories I have, and I am not alone. The longer we are single, the more stories we have. I spoke with women too to see if my observation was fair and not just geared toward men. I heard the same things over and over again that reflected my personal experience. Why can’t we give people a fair chance when we meet them? It is hard for some to leave their past hurts behind and begin again.

So, at what point in our collective post-divorce single-ness do we wipe the slate clean and have a brand-new experience with each person we meet? Do you remember the Etch-A-Sketch? I loved that toy. Creating a new picture by turning and adjusting the knobs and then shaking it to clear out the picture. Using this example, I shake off any experience, situation or issue so that I don’t bring it with me when I meet someone new. This is a great visual reminder that every man deserves to start with a clean slate (and so do I, for that matter).

The second challenge is communication style.

Smart phones have altered the way we communicate with each other. I’ve had a difficult time with men who only want to text and not talk or not talk very often. There is so much you loose in texting only. Miscommunication happens frequently when the context is misunderstood due to the reader not being able to gauge the sender’s intention.

This became apparent in one of my most recent dates. We met for a drink after a great phone conversation. We had a great time however chemistry can be hard to gauge on a first date. At the end of the night, we agreed to see each other again. He asked me to let him know when I was available, and dating at 50+I gave him several options for the following week. We texted a few times, but he never asked to see me again. In rereading his short texts, I felt like he was throwing me crumbs to keep me interested, on the hook and to be a “filler” if he didn’t have something better to do. I let it play out and the second date never happened. Whether this was his intention, I don’t know, but I felt that our communication style did not match at all. When I am interested in someone, I make the effort to chat on the phone. It is important to hear the inflection and tone in someone’s voice.

The third challenge is the pressure to only date one person.

How is it possible to decide so quickly if you want to be exclusive with someone? Some of my dates made me feel pressured to be exclusive after one date. On a phone conversation with one man, he asked me to stop seeing other men before I met him for the first time. This comes across as a confidence issue. I completely understand and agree that it is important to be in an exclusive relationship, at the appropriate time determined by both people.

Dating is supposed to be fun, isn’t it? Why do we have this intense focus on trying to find “the one”? Why is it not acceptable to date multiple people at a time before you decide which one is the best match? A large part of this is being completely honest and letting men know I’m not seeing only them. I’ve experienced a lot of judgement around dating and wanted to get a better perspective. I began reading Love in 90 Days by Diana Kirschner, PhD. I highly recommend this book. The most enlightening chapter is “Dating Three to Find the One”.  This made complete sense! Women bond more quickly than men and we tend to overlook things in the beginning of a relationship. One of the best pieces of advice I’ve heard, “Women marry men expecting them to change and they don’t while men marry women expecting them not to change and they do.” I’d like to ask that we just loosen up a little and have some fun.

The fourth challenge is appropriate dates.

This is HUGE for me and plays into the first challenge. Because people are now so guarded, what is considered a suitable location and interaction for meeting is different than in years past. Frankly, I’m often caught off-guard with these requests. I was invited to noisy bars for first dates. More than once I was invited to a man’s house for a second date. Some of my dates asked to come to my house to watch Netflix and “chill”. Others requested we meet at the mall and people watch. Men sometimes get offended when I don’t ask them to come home with me after a first, second or third date. I don’t know this person and certainly do not feel comfortable in any of these situations.

How have we gotten so off-track with what is acceptable at our age?

I want to get to know someone over time in different circumstances and settings. A visit over coffee, glass of wine or a casual meal in a nice quiet location with some ambiance helps to engage in conversation. I like to start slow. It is important to take time to chat, experience each other’s energy, personality, demeanor and attitude in an appropriate location. I do believe a lot of factors contribute to this challenge, which I continue in Challenges of Relearning How to Date – Part 2.



Amy Jones

Amy Jones 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. 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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