7 Things to Consider When Dating Over 50

7 Things to Consider When Dating Over 50

By Joyce Glass

Over thirty years ago, at 17-years old and a senior in high school, I went on what I thought would be my last first date,  then I married at age 20. Fast forward to October 2021, after moving to Waynesville, N.C. in May, finalizing a divorce in June, and settling into a new job as manager of Sassafras on Main, I wanted to date. I hoped to meet someone as I went about my daily life like in a Hallmark movie, and we would hit it off and date. Now, stop laughing. It could happen, but it didn't for me. Let’s face it. This doesn’t happen to many people these days.

And if you live in Waynesville, you know the dating pool is slim for singles over 50. Of those available, I found few of them, if any, desirable. There may be some nice eligible men in the Waynesville area, but I never met them. 

I joined in October, after talking with a very happy couple in the store where I work. They had met online and encouraged me to try online dating. To be honest, I just didn't like the idea at first, but after talking to them, I decided why the heck not. It beats sitting in my apartment alone every weekend cleaning. 

Since I moved here, I've met some fabulous girlfriends, and we go out on occasion. However, I wanted some male companionship too. 

Each new bachelor taught me something about dating over 50. Turns out I like online dating more than I thought I would. It is nice to learn a little bit about someone before meeting them face-to-face. As well as, being able to filter quickly through the no’s from the hmmm… maybe’s. I enjoyed talking on the phone to get to know them better which made the first date a little less stressful. 

Now, this is purely from my experience and I’m clearly not an expert. However, all of life is learning about things and how to interact with other people.

1. Don't compromise for companionship. 

Bachelor #1 - Our magical first date left me giddy for days. We spent the entire afternoon and evening together, strolled through downtown Waynesville, went out for lunch and dinner, and took a drive on the Blue Ridge Parkway. Went out the next night too. Then he had to go back to where he lived out of town. 

A week later I shared my spiritual beliefs with him, and we realized we had drastically different spiritual and political beliefs. We had talked about them some during our first conversation, but not in great detail. I meant one thing, and he thought I meant something completely different. It broke my heart to end the relationship, but better after a week than after a year or two. 

I knew in my heart this would not be a good fit, and did not want to force a relationship I knew would not be good for either of us no matter how many good things there were about him. 

 Know what you believe and don’t compromise for companionship. It will hurt both of you in the long run.

2. Look for a connection.

Know what type of person you are looking to be with, whether it is a casual relationship or something more serious. 

Bachelor #2 - Sweet guy and a perfect gentleman, but I didn’t feel a connection or sparks flying. It disappointed him, but I was honest. 

I learned this one a long time ago the hard way. I am a recovering people pleaser, and I will not date someone just because they are nice to me if I don't feel any kind of connection to them. For some women this is an easy decision, but for those of us who don't want to hurt people's feelings or make them feel bad, it is a struggle. This was a big step for me, because I don’t want to settle.

 3. Guys have deep feelings too. Be aware of where they are emotionally. 

Bachelor #3  - A gorgeous and sweet guy, we had a friendly date, but I could tell he was not connecting with me. We talked off and on for a few weeks and had some deep conversations about each other’s lives. Someone deeply hurt him recently, and he didn't need to be dating. 

Both people need to be in a healthy emotional state for a relationship to work best. If you are not in a place where you feel you are healthy emotionally, don't be afraid to take the time to work on yourself. This will save you much heartache in the long run. It is not fair to the other person, if they don't know what demons you are fighting. 

4. Listen to your gut.

Bachelor #4 - Again, another personable guy, but my gut told me from the beginning this might not be a good match. We met for dinner and had a pleasant conversation, but he even said at the end of dinner he didn't think we were a good match. I agreed. He reminded me way too much of my ex. 

When you know the kind of person you want to be with, and you are in a healthy emotional state then trust your gut when it tells you something is off. I didn't listen to mine and married someone I should not have married. Hindsight is 20/20 for all of us. 

 5. Talk on the phone before you meet in person. 

Bachelor #5 - The first time he talks to me on the phone he is drunk. Should have told him to call me when he was sober. However, it was quite hilarious. I went with it, but a strange call. He asked me to meet him for dinner the next night after work. I agreed and was very excited. Got all dressed up, and he cancels three hours before the date, said he couldn't afford to drive so far and take me out... HUH? Then why did you bother asking me out knowing all of this. 

Talk with your girlfriends too. Found out this guy had talked with one of my friends online, but they never dated. He has some serious mental health issues and struggled with as well as financial issues. I felt bad for him but didn't want to date him. Plus, he was close to two hours away from me. Not ideal. 

6. Experimenting can be good. 

Bachelor #6 - Another nice guy, but a little deceptive, saying he was about 13 years younger than his actual age on his profile, but he stated in his profile description his age is not accurate. I missed reading it when I read the profile. We had a delightful couple of dates, and then he revealed his true age. 

He was nineteen years older than me! About old enough to be my dad. I know this does not bother some people, but this one bothered me. I just couldn't. Know what you are comfortable doing.

It was good to get to know him on a date, but I knew this was not a relationship I wanted to pursue. Part of the dating process is learning what you don’t want to figure out the kind of person you are seeking.

Value yourself and others will too. 

7. Enjoy the journey! Some will surprise you.

Bachelor #7  The man melts my heart. He messaged me once before, and I ignored him. I wasn't sure because he is eleven years older than me. Ten was the limit I had set. Then he messaged me again. I checked out his profile closer, and he intrigued me. We chatted on the phone for two nights before we met.

During our first conversation, I loved the sound of his voice. The sound of a man’s voice never really made a difference to me, but something about his voice made me happy. I didn’t know what to expect during the date. He had many great things on his profile I liked, but I hesitated about his age. Would we have anything in common? Would he think I was too young? Too fat? Too much to handle? 

The date ending up being amazing. We enjoyed talking for a long time after dinner, and shared some good laughs. I felt very comfortable being around him and wanted to see him again.

When we talked before the date, we discussed going for a hike on our second date if the first one went well, and as we were saying goodbye I mentioned going for a hike the next day. He said he had plans already. My heart sank. I knew he lined up a date for the next day. What other plans would he have on a Sunday afternoon? I suggested maybe some other time, and politely left. 

In my car I fumed. I decided to quit dating for a while. The ups and downs were getting to me. I needed a break… Then he calls me less than five minutes after I drove off. He admitted to having another date lined up but said he would cancel. He had an enjoyable time with me, and thought about how silly it would be not to go on a hike with me after having a great night together. Smart move… 

I’m so glad he did. Over the past three months, I have loved getting to know Rusty. He is kind and thoughtful. We share many common interests, love to hike, explore, dance, and spend time with each other. I am enjoying the process of getting to know someone new. 

He makes me smile when I hear his voice or see him. We laugh and have the best time together. We share a love of music and dancing. Right now I focus on growing together and not worrying about where this relationship will go in the future. It makes life more fun and freeing to allow the relationship to grow organically. 

From the Man's Perspective:

Rusty divorced in 2010 at 51. He graciously shared some of his insights on dating over  50 for you. I thought you would enjoy a man’s perspective too. 

Rusty shares:

Dating over 50 can be interesting, fulfilling, and yes, complicated. Many people, especially women, stayed in difficult marriages for the benefit of children. After the children leave the nest, they divorce and look forward to finding a friend or lifetime partner. 

Everyone pursues different goals when looking for a partner which can complicate things even more. Know what your goals are as you explore dating again. 

There are some advantages and disadvantages to dating over 50.


  1. Most of the time the children are grown and you don’t have to worry about how a new relationship will affect them. 

  2. Many people retire and have more free time to travel or sit on the porch with someone special with a cup of coffee or a glass of wine.

  3. Often have more money to travel and experience the world together.

  4. Doing life with a partner is much more fun. 


  1. As we age, we become set in our ways and hesitant to let someone in who may upset our routine. 

  2. Sometimes children are still at home and will cause friction in the new relationship. 

  3. Some jobs make it difficult to have time for a dating relationship.

  4. Health issues can make dating a challenge.

  5. Distance can be a struggle to see each other often. 

  6. Some people are still heartbroken over a past relationship or loss of a loved one. They are slow or unable to be vulnerable with someone new. This is required if you want new love in your life.

Dating is a Journey

Dating is similar to life. It is a journey not a destination. Enjoy the journey. Finding the next Mr. Right may be your ultimate goal, but take time to soak in the process. Take time to really get to know someone, and be willing to learn from each new experience. You may date or kiss fourteen frogs before you find a prince. You may think you found the prince and he turns out to be a toad. 

Be willing to release and forgive those who are not kind to you or just plain don’t work out. If you are struggling to find someone to connect with you,  make sure to work on yourself. I’m not saying you have to be perfectly emotionally healthy to date. No one goes through life without pain or issues. Own your issues and know how to deal with them. 

Like I mentioned, I am a recovering people-pleaser. I know this and I learned it is a choice. I can choose to do something kind for someone because I care about them, but I don’t have to do  things for people to make them like me. They either like me for who I am and the way I am, or they don’t.  

I carry around many insecurities like most women. I know they are lies rolling around in my head to make me believe I am not smart enough or pretty enough to be important to someone else. There are many outstanding books and videos to help you overcome the “I am not enough” insecurites. We all have insecurities, and most of them boil down to this one line, “I am not enough.” Don’t let your insecurities control you. Find healing and freedom to be the beautiful woman God created you to be in this world. 

I battle insecurities just like everyone in this world does. Learn how to talk to yourself kindly and with confidence. Then you will control the self-talk in your head instead of the stupid insecurities controlling you. 

May your dating journey contain many twists and turns to keep life exciting and a couple of surprises along the way. 


Joyce Glass is a writer and lover of most things chocolate! Her desire is to encourage you to live your life to the fullest. She’s living her dream to live in the mountains of western North Carolina. Come say hi to her as she manages Sassafras on Main in Waynesville. 

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