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Challenges of Relearning How to Date: Part 1

challenges post divorce dating

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Author: Amy Jones

revised 11/25/2020
originally posted 3/25/2019

Dating is different now

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 remarry, we are on a search. You would think because we live in a highly populated area with numerous divorced singles 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 almost nine years. During that time, I 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, mutual friends introduced us. I developed the other two relationships online. As I stated in my last article, Stop Missing This Important Aspect Of Successful Dating At 50+, I no longer date online. I recognized over time that it is really hard to make a connection in a virtual world. The time spent yielded few results. I may go back at some point, but for now I need a break from it.

dating at 50plus

It takes time and patience

I realize it may take longer than before to go back to the basics of dating. It takes time these days to meet and connect in person. 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 need to relearn how to date. So, I contemplated the experiences I had in the past  and reviewed what worked and what didn’t in the time I’ve been single. I came up with quite a few challenges. The following is part one of a three-part article.

The first challenge: People are guarded 

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 other women to see if my observation was fair. You know what? I heard the same things over and over again that reflected my own personal experience. Why can’t we give people a fair chance when we meet them? It is hard for some to leave past hurts behind and start 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. With it, it was easy to turn and adjust the knobs to create a picture, then shake it clear to start again. Using this example, I shake off past experiences, situations or issues so 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 for that matter, so do I.

The second challenge: communication 

Smart phones forever altered the way people communicate. I have a difficult time with men who only want to text and not talk or not talk very often. There is so much you loose when you only text.  Miscommunication commonly happens when the  reader is not able to gauge the sender’s intention.

This was apparent in one of my most recent dates. After a great phone conversation, we met for a drink. Though we had a great time, though I wasn’t sure there was chemistry; it’s hard to tell 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 provided several options for the following week. We texted a few times, but he never asked to see me again. In rereading his short texts, it seemed he threw 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 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: Pressure to only date one person

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

Dating is supposed to be fun, isn’t it? Why do we have this intense focus 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? It’s important to be completely honest and let men know I see other people.

In conversations with other women, I heard a lot of judgement around dating.  I wanted to get a better perspective and read Love in 90 Days by Diana Kirschner, PhD, a book I highly recommend. The most enlightening chapter is “Dating Three to Find the One”.  This made complete sense! Women bond more quickly than men and many tend to overlook warning signs at the start of a relationship. I want to loosen up a little and just have some fun. One of the best pieces of advice I heard from a friend was:

“Women marry men expecting them to change and they don’t while men marry women expecting them not to change and they do.” 

The fourth challenge: Where to go on a date and what to do

This is HUGE for me and plays into the first challenge. Because people are now so guarded, what is considered a suitable location to meet is different than in years past. Frankly, I’m often caught off-guard. I was invited to noisy bars for first dates and to a man’s house for second dates. Some of my dates asked to come to my house to watch Netflix and “chill”. Still others requested we meet at the mall and people watch.

And then there’s the expectation of sex. Men sometimes take offense 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 do not feel comfortable rushing into a physical relationship. 

How have we gotten so off track? 

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 encourages easy 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. So many factors contribute to the fact that dating is difficult at our age, a topic I explore further 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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