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Challenges of Relearning How to Date – Part 2

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By Amy Jones

originally posted 4/15/2019
updated 12/1/2020

Dating challenges at age 50+

As I started to write this article, I realized how many challenges we face dating at 50Plus. The spectrum of why men and women are single at our age is enormous. Some are single for the first time since college. Other people are single after a first or second or even third marriage. And, some are not married currently due to the death of a spouse. Others are single at this age because we waited to get married later than others and it didn’t happen. We all have one thing in common:  we are by ourselves due to our circumstances. Another similarity – we all need to connect, and to feel supported, cherished and loved.

Why has it become so challenging?

Dating is different than it used to be. How we interact and meet is not the same because we are not the same. We live in a rapidly, ever-changing environment. How do we evolve and stay open to receive what we ultimately desire? It can seem like a full-time job to find the right fit with the right person. Sometimes the job is rewarding and sometimes it’s just tedious. It takes commitment, courage and consistency to continually put ourselves out there to find and receive the love we deserve and want. 

As a quick recap:

The first challenge is people are more guarded than before. 

The second challenge is communication style.

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

The fourth challenge is the appropriateness of dates.

And continuing the challenges:

The fifth challenge involves vulnerability.

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It’s easy to hide behind our screens when we interact with a potential date. We can do or say anything when we have a shield to protect us. But when it’s time to actually get in front of the other person, can we allow ourselves to show up in our true form? I am guilty of using the screen to hide for a long time. After my divorce, I was extremely vulnerable. My deep hurt surfaced quickly and often, and I recognized I was not yet healed from that part of my life. It was two years before I felt ready to seriously date. I took time for myself, explored being single and rediscovered myself.

Once I became more self-aware, I over-corrected. I became a Teflon shield of deflection, and didn’t expose my soft side or my vulnerability to anyone. This behavior, overcompensating, was not healthy. Eventually I learned to balance my vulnerability with security and trust in myself.

So how vulnerable should we be?

Even though people may say they want you to tell them “everything”, that’s generally not the case. I learned the hard way that some point, they can’t handle the truth. It’s a very delicate line when you date; you need to be just vulnerable enough so the other person doesn’t feel overwhelmed. You want them to be compassionate and understanding, but you don’t want them to feel obligated to fix you. 

Brené Brown speaks about a “vulnerability hangover” in her book Daring Greatly. She says, “A vulnerability hangover conveys the regret associated with pushing the limits of the honesty comfort zone.”

Learning the balance of vulnerability and fortitude is a big challenge. It’s important to be vulnerable with our partners to some extent, but you do not want them to start to feel like a parent. You can only create a strong and loving bond between yourself and someone else if you share your true self.

The sixth challenge involves appearance and self-pride.

You might think people generally take the time to present themselves in a positive and polished manner. However, over time, I saw a pattern with both men and women. I heard countless stories from men about how their date showed up in some random outfit, or was unkempt or inappropriately dressed for the venue. It seems yoga pants and flip flops are often the attire of choice. Frankly, I also experienced a little shock at how my dates showed up. One guy wore workout clothes to a nice jazz club, another sported a wrinkled shirt and pants when we met at Starbucks, and one man wore an ill-fitting, extremely tight t-shirt with shorts that left NOTHING to the imagination for a lunch date. It doesn’t matter where you meet, take some time to look presentable. If you don’t care about your appearance for the first meeting, how does that reflect how you feel about yourself?

I believe it is important to make a good first impression. As the saying goes, “you never get another chance to make a first impression.” Smells are very important to me and if someone shows up not smelling good, clean or fresh, it is a huge turn-off. Taking the time to ensure teeth have been brushed and breath smells good, clothes are not wrinkled and fit appropriately, and shoes look nice are just a few simple things to check before meeting someone for the first or second time.

The seventh challenge – who pays the bill?

This one is REALLY awkward! The rules vary tremendously from situation  to situation and person to person.

 Here are some ways people handle the payment issue:

1) The one who invites is the one who pays.
2) Always go dutch.
3) First time he pays, second time I pay.
4) Let him pay.
5) Discuss it when you get there.
6) See what happens when the check comes.

dating 50 plus

NONE of these feel good to me. One guy invited me to meet at Starbucks for coffee; he insisted on paying, but commented on my “expensive coffee” when I ordered a latte. Another time a man that invited me to a nice wine bar insisted on drinking “the best cabernet” at $20/glass; after he paid for my one glass of wine, he was insulted I didn’t ask him to come home with me. (Side note – he was attractive but had really, really bad breath).  Once, when I invited a man to meet me for dinner, we agreed upfront to pay for our own meals. When the bill came, he told the waiter to spit the check; I had only an appetizer for my meal and he ordered steak. Now, these aren’t the only experiences I’ve had. I have had some “goodish” ones too, but these are good examples of the challenges many of us face when the bill arrives.  

Ultimately, who pays?

Establishing guidelines up front helps ease the awkwardness tremendously. Every individual and every situation is different, so it’s important to try not to judge the person or circumstance. I’m happy to pay for myself because I can, but I’m also pleasantly surprised and grateful when my date picks up the check. Regardless of who pays, I order exactly what I want and be myself.

The eighth challenge is the big one: SEX.

Wow, what incredible hang-ups we still have about sex. This issue is the biggest challenge for me. Sexuality is a big part of who we are; it allows us to express ourselves and receive an intimate connection. Sex is good, sex is natural, sex is amazing. Why is it such a HUGE challenge?

dating 50plus


We need to look at sex through a completely different lens at this point in our lives than when younger.

Ask yourself the following questions:

Why is sex important or not important?
What are the advantages and disadvantages of sex?
What do I want to receive from having sex? (i.e. Is it purely physical? Do you need to feel an intimate bond? Has it been a while and you need to break that cycle?)
Am I comfortable discussing safe sex and using protection?
Will I feel guilty if it is just a one-night-stand?
What does sex mean to me?

The reasons we have sex are very personal.

Keep this in mind; the longer we are single, the less we get touched, and the more we desire it. We might feel off-balance if we want this type of intimacy and don’t get it. This is NOT a good thing. Touch is very important to our health and well-being. It releases important brain chemicals like serotonin, oxytocin, dopamine and endorphins. These feel good/happiness brain chemicals stabilize our mood and help reduce anxiety, stress and anger. Sex is a wonderful combination of physical, mental and emotional stimulation. Exuding confidence and being comfortable with who you are and how you look is extremely sexy; both outside and inside the bedroom.

The challenge is not to put pressure on yourself to have sex. Allow it to happen naturally through the flow of the conversation. Create energy between yourself and another person without expectations of where it might go afterwards. If it’s right – and when it’s right – it will happen.

By the way, I am a huge proponent of safe sex. Sex is healthy and protection helps alleviate worry, allowing a greater expression of physical desire. My mantra is always be prepared!

The bottom line

Through these challenges, I learned it’s important to give every man a fair chance with fresh eyes and a renewed perspective. I refuse to become jaded or negative like so many people I know that are single. I plan to continue to be open to the emotions and the experiences, and work to live in the moment so I won’t miss the connection when the right man appears. My ultimate and deepest desire is to find a healthy, balanced, committed relationship. An important part of the process is to learn and grow through my dating experinces. At some point, hopefully in the very near future, I won’t need to think about challenges any longer…


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