Dating at Midlife/Not sure what went wrong


About a month ago, I connected with a guy through online dating. I liked what he had to say about becoming friends, becoming best friends any possibly falling in love. We began talking and texting and set a date to go out.

On our date, we saw some of my acquaintances who later wanted to know how long we had been dating; they couldn't believe we were on a first date because we were so comfortable with each other.  He said that it was difficult to get back into going out because he preferred the way it had been when he was married where they were happy just staying at home together. At the end of the evening, he said he had really had a good time and asked if he could kiss me goodnight. It was a very nice kiss; I was a little embarrassed when he said I was a good kisser but happy there was some chemistry. He texted me later that night to make sure I got home.

From that point on, we sent texts each day and talked occasionally. (We work different hours.) I kept thinking he would ask me out again but he hasn't. I want to blame it on the fact that he has been working a lot of overtime and is tired on weekends.

There were a couple of days that he did not respond to my messages and I thought it was really strange. He finally called and wanted to know why I was ignoring him. It turned out to be a problem with my phone not receiving his multiple messages. The benefit was that we had the opportunity to express our interest in each other.

I typically am very passive in relationships so I decided to take a little more initiative this time as it has been suggested that guys may get the idea I am indifferent. After we went out and had such a good time, I thought it would be fun if we went to a concert. I got tickets and asked if he would like to go. He said thanks that it sounded good. I was happy that I took a risk and didn't get rejected.

Now to the problem. I sent him a text three nights ago about the time he would have been on break and asked how work was going. He replied that he had taken off work. I asked if he was partying but did it in jest. He replied that he was planning on it but there wasn't much going on at time. So I told him things would probably pick up later. At first I thought he was joking with me after what he has said about not liking to go out but then decided he was serious. It bothered me that he finally was off work with the energy to go looking for a party yet he hadn't asked me out.

I have not contacted him since and I have not heard from him. Although I have friends who will go to the concert with me, I am very disappointed that he has ended contact with me and apparently doesn't plan to be the one to go with me.

You may be thinking the problem is with my phone again but it is working fine this time. I've got all these people telling me to just wait and let him contact me if he wants to. This is what I prefer since I feel it is his place but I just don't know what is best. I don't want to force myself on him and I wonder it is a case of his only being interested until someone better came along. I am 47 and he is a year younger and it seems to me I should not be so confused at this point in my life.

Any advice on what I should do at this point if I am still interested in him or how I should handle a situation like this in future?

Hi Renee, I know how frustrating dating can be, but rest assured nothing "went wrong". Everything is going the way it's supposed to go. It is so difficult to try to understand peoples failings. They behave differently from the way we would or want them to. One thing is for sure and that is you don't want to get  involved with someone who does not meet your criteria. When you set parameters on how you expect to be treated, it will manifest itself. We will not wonder why someone behaves the way they do, we can concentrate on what we want for ourselves.
He may call you again. You can decide if you want to discuss what doesn't work for you in relationships or friendships. If he does not call again then know that this is not the person you want to attract in your life. The clearer we are as to the type of person we manifest the more likely we will get what we ask for. I wrote a very clear list of everything I wanted from a partner. I was very detailed in my criteria. I then decided what percentage of my list is negotiable.You will actually have a bar for you to think about when you meet other people in your life. Shortly after my list I met a man who I am marrying in May. My partner made 99% of my list. The only criteria he did not meet was his height.I met my best friend. I know you will have the same wonderful gifts happen to you when you're clear. Happy writing and find that almost perfect partner. :)  

Dating at Midlife

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Lauren Stevens


I can answer all questions pertaining to dating, dating at 50+, online dating, health and sexual issues regarding relationships.


I have been a life coach and all expert coach for over 15 years.

I have founded and facilitated Life After Divorce a coaching program that promotes and enables life changing events. I also facilitated Transitions a support group for the traumatic experience of people going through divorce and the newly divorced.

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