Confessions from My Online Dating

I dated online.

The following stories you are about to hear are true. Only the names have been changed to protect the innocent.

I know some might find this shocking. However, after I lost my partner of 29 years, I made the conscious decision not to live the rest of my days on this earth alone. Even God said it was not good for man to be alone. I could live alone, but I did not want to.

I loved having that partner who had your back. Someone to laugh with, someone to share your life with. Especially someone with whom I had basically “grown up”.

We had a lot of things in common, and we each had other interests outside of our relationship. We each were not perfect, but we were perfect for each other. His strengths complimented my weaknesses, and vice versa.

A year or so after he passed away, I began contemplating dating. But at my age, and with my limited dating experience, I wasn’t sure how to go about it. I had not dated in 3 decades.

Even though my friends and family knew I was “suddenly single”, I was not meeting any single men my age. And since I worked from home, I did not meet anyone “at the office”.

My prospects seemed slim to nothing, and I decided to try reaching out to single men online.

Well, let me tell you, that is NOT for the faint of heart! At first it was exciting, and I had a lot of men reaching out to me! But I was cautious, both because I had never done this before and because even though I wanted to “talk” to single men, I was hesitant to put myself out there in person. There was no guarantee that the person on the other end of the internet was indeed the person they claimed to be.

I will not go into all the details, but there were a couple of things I learned about myself, and about the dating “trenches” at my age (which is, let’s just say, “more than 50”).

I learned these things the hard way, after a few unsuccessful “attempts”. I kept feeling like I was missing something, and I should be better able to determine who was a good fit.

In order to “think it through” logically, I made a spreadsheet (oh yes, I did!!), and started tracking what things I liked about which guys. I was analyzing my “results” trying to find a pattern. What things did men do that would make me think they would be a good mate?

Here is what I learned:

First, if the relationship was making me feel uncomfortable, I needed to trust my judgement and not pursue it. If he is too pushy or too physical for me in the beginning, it will only increase as he spends more time with me. Anything that bothered me in the beginning, really did not sit well with me, fit into this category.

One man I talked to for a while, and then met in person, seemed like we could be a good fit. But he wanted to talk to me every night and if I already had plans, he would be upset, sometimes even remarking how I didn’t invite him.

He lived a distance away, and when I asked if he was in the area and would have liked to go, he was vague on his answer.

The next time he texted me his guilt trip after a night of axe throwing, I promptly replied that this was not a relationship I was interested in pursuing. Other than our first meeting, he never asked me out somewhere but had just continued to comment when I went out with friends.

Second, I learned I wanted someone with similar interests. I did not have decades to develop new interests, and I already knew what I enjoyed in life. I wanted someone who felt family and faith were important, and who loved to dance and roller skate!

I sat across the table from one man as he explained all his ailments that hindered him from dancing. I was surprised because the night I met him he asked me to dance. However, I was not yet ready to trade in my roller skates for a walker!

Third, I learned communication skills are a MUST for me! I often joke that I want someone who, when we get old and things don’t work, I can still enjoy a good conversation while we sit in our rocking chairs! Even though I laugh about it, I know it is true.

One guy I dated briefly, hardly ever talked. At first, he texted me. But after a couple of days, he informed me by text, “I don’t do texting”.

He wanted me to call every day so we could talk. But, talking to him meant me asking questions, and him responding with one-word answers.

We were on the phone one time at my sister’s house, and I was tired of trying to think of things to ask him. So, I was quiet. And so was he.

After a couple of minutes my sister looked puzzled and asked, “why aren’t you guys talking?” I shrugged.

It wasn’t too long after that I TEXTED him that I was looking for someone I could go on dates and do things with…we never went anywhere. He would tell me when HE was going somewhere, and I was welcome to meet him there, or not. I chose NOT.

One of my worst dates was a man who told me his life story over dinner. Past dinner he regaled me with all his dos and don’ts he expected from a wife. And he told me about his recent wife who passed away, and indeed, her funeral was a few weeks ago.

“But” he said, “I know I want a wife in my life.”

Which may sound like exactly what I was looking for--but this definitely was not!

Throughout the evening I had tried to talk. Several times I started a sentence only to be interrupted with his, “oh yeah, and I don’t like…”. He seemed more concerned with giving me his marital requirements than with finding out anything about me.

 Hours later he paused and said, “Well, tell me about yourself, you haven’t said a word.”

 I just smiled. I had LONG since grown exhausted of listening to him!

 He called me on my drive home and said he would talk to me all the way back.

 He did not ask me if I wanted to talk all the way home. And indeed, I did not. I really did not want to spend another moment talking to him (or more accurately, listening to him!).

 I made up some excuse about needing to concentrate on my driving and before he could object, I quickly said, “Okay, I’ll talk to you later!” and hung up. It was extremely liberating!

 Several days later I messaged him and said I didn’t think we were a good fit. He was surprised.

 I’m not surprised that he was surprised!

There were a few other relationships that didn’t work out for one reason or another. Some I met in a singles group, some online.

 One day this guy “liked” me online. I checked out his profile and thought he had possibilities. I returned the “like” and messaged him. He thought I sounded like “fun”. We went back and forth several times learning more about each other until he sent me his phone number.

 

I decided to take the next step and talk to him on the phone. That first phone call was fantastic! I had a wonderful time talking with him. He was funny, and he asked questions about me, and he laughed with me. We spent the next week talking every night and every time I enjoyed it thoroughly! Every time I hung up the phone I was smiling! We just hit it off great and I looked forward to talking with him.

 After that week we decided to meet in person. He was just as fun in person as he was over the phone. We enjoyed our time together. We skated, we danced, we bowled and went to the movies together (not all in one day!). And most importantly, we talked. I shared my story, and he shared his. We both were looking for someone with whom we could spend the rest of our life.

 
We are now engaged.

 Now I’m not recommending dating online, and I’m not trying to say I am some kind of relationship expert. But what I am saying is that you should know what things are important to you, and then measure your dates by those things. Do not compromise in looking for those things. Take your time and find a good partner. Otherwise, you could end up with someone who temporarily likes you for superficial reasons, instead of someone you can truly spend the rest of your life with.