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Challenges of Relearning How to Date – Part 2

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By Amy Jones

As I began writing this article, I realized how many challenges we face dating at 50 Plus.

The spectrum of single men and women, at our age, is huge. Some are single for the first time since college. Some are single after a first or second or even a third marriage. Some are single due to the death of a spouse. Like me, some are single after waiting to get married in our late 20’s-early 30’s. We all have one thing in common:  we are by ourselves due to our circumstances. We all need to connect, to feel, to be supported, to be cherished and to be loved.

Why has it become so challenging?

Dating has changed. How we interact and meet has changed. We have changed. We live in a rapidly, ever-changing environment. How do we evolve and be open to receive what we ultimately desire? Being open to finding the right fit with the right person can seem like a full-time job. Sometimes the job is rewarding and sometimes it’s tedious. It takes commitment, courage and consistency to continually put ourselves out there in order to find and receive the love we deserve and desire from our beloved.

As a quick recap:

The first challenge is how guarded people have become.

The second challenge is communication style.

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

The fourth challenge is appropriate dates.

And continuing the challenges:

The fifth challenge is being vulnerable.

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It’s easy to hide behind our phone or computer screen when interacting 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’ve been guilty of this for a long time. I was too vulnerable after my divorce. My deep hurt would surface quickly, and I recognized I had not healed that part of myself and my life. I would not be ready to seriously date for another 2 years. I needed to take time for myself, explore being single and rediscover me. Then I over-corrected and became a Teflon shield of deflection, never showing my soft side or my vulnerability. This was not healthy either. I had to learn to create a healthy balance of vulnerability with security and trust in myself.

I’ve learned that even though some people say they want you to tell them “everything”, at some point, they can’t handle the truth. This is a very delicate line in dating; learning to be just vulnerable enough so that the other person doesn’t feel overwhelmed or that they have to fix you as well as being compassionate and understanding with yourself and the other person.

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.”

So, learning the balance of vulnerability and fortitude can be challenging. I believe that, in all of our hearts, we truly want and desire to be vulnerable with our partner which creates a strong and loving bond between two people.

The sixth challenge is appearance and self-pride.

You would think that this would be a non-issue and  people would take the time to present themselves in a positive and polished manner. However, over time, I began to see a repeating pattern with both men and women. I heard countless stories from men about how their date had shown up in some random outfit or unkempt or inappropriately dressed for the venue. It seems that yoga pants and flip flops were the attire of choice. Frankly, I’ve been a little shocked at how my dates have shown up on a first or second date:  workout clothes (we met at a nice jazz bar), wrinkled shirt and pants (we met at Starbucks), ill-fitting, extremely tight t-shirt and shorts that left NOTHING to the imagination (we met for lunch). It doesn’t matter where you meet, the important thing is that you have taken time to ensure that you look good. If you aren’t concerned 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 is who pays?

This is REALLY awkward! There are a number of unspoken rules about this and I’ve found that from situation to situation and person to person it can vary tremendously.

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Here are a few of the rules I’ve been given:

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.


NONE of these feel good to me. I was invited to meet at Starbucks for coffee by a man who insisted on paying but made a comment about my “expensive coffee” when I ordered a latte. I was invited to have a glass of wine at a nice wine bar by a man who insisted on drinking “the best cabernet” at $20/glass and, after he paid for my one glass of wine, was insulted that I didn’t ask him to come home with me. He was attractive but had really, really bad breath. I invited a man to meet me for dinner and we discussed paying for our own meals. When the bill came, he told the waiter to “split it” – I ordered an appetizer for my meal and he ordered steak. Now, these aren’t the only experiences I’ve had. I have had some good’ish ones, but these are just an example of how we’ve made this such a challenge.

Ultimately, who is the one who pays? Establishing guidelines around this challenge will certainly help ease the awkwardness. Every individual and every situation is different, and it’s important to try not make any kind of judgment about the person or circumstance. I’m always open to paying for myself because I can and I’m also pleasantly surprised and grateful when my date pays for me. Regardless of who is paying, I’m going to 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 has been one of the biggest challenges I’ve had so far. I’m a pretty outspoken person and am open to discuss just about anything. This is one area where I have so many stories, I could write a book! Sex is a vital part of being who we are; expressing ourselves and receiving an intimate connection. Sex is good, sex is natural, sex is amazing. Why is it such a HUGE challenge?

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I think we have to look at sex through a completely different lens at this point in our lives and ask the following questions:

Why is sex important or not important?
What are the advantages and disadvantages of having 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 confident discussing safe sex and using protection?
Will I feel guilty if it is just a one-night-stand?
What does sex mean?

The reasons we have sex are very personal, however keep this in mind; the longer we are single, the less we get touched. The less we get touched, the more we desire it. The more we desire it, it the more off-balance we might feel. This is NOT a good thing. Being touched is very important to our health and well-being and 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 putting so much pressure on having or not having sex. Allowing it to happen naturally through the flow of the conversation, creating energy between two people and having no expectations of where it might go afterwards are all beneficial ways to overcome the challenge of whether to have sex or not. Sex is healthy. I am a huge proponent of safe sex. Using protection helps alleviate worry and allows for a greater expression of physical desire. My mantra is always be prepared!

Encountering all of these challenges, I’ve learned that I have to give every man a fair chance with fresh eyes and a renewed perspective.

I will not become jaded or negative like so many people I’ve met who are single. I will continue to be open to the emotions, the experiences and being in the moment so that I will be aware of the connection I feel when the right man appears. Having a healthy, balanced, committed relationship is my ultimate and deepest desire. Learning and growing through my dating patterns are all part of the progress and process. I recognize that, at some point in the very near future,  I won’t have to think about challenges any longer…


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