2017 advice dating dating chronicles failures relationships

Dating Chronicles: Insecurity

Have you ever dated a man or woman with real insecurity issues? I have. I dated a few men who had issues with women because their past relationships were so jacked up. They literally were living in a perpetual state of unhappiness and decided that deep down inside all women were bad.

It was hilarious at first and then a little depressing. How can we even begin to build if you are making me pay for the mistakes of your past girlfriends? Prime example, a couple of years ago I met this great guy on-line and we went out on a date. It was a combination between our first and second date.

How’s that possible? Well, we had stayed up the night prior talking all night. I mean it was like 5 hours of conversation. I fell asleep and then called him at 2:45 the next morning. He called me back at 4 am and then we talked until again until about 7 am. He was such a great conversationalist so I told him that either we had to meet for breakfast or I needed to get some sleep because I was exhausted.

We agreed to meet up and grab breakfast and all was cool. My breakfast sucked, but he was nice. After breakfast he said he had to run his Saturday errands but wondered if I would go out with him that evening. I agreed.

We went to dinner to this cool pizza place because pizza is my favorite food. It was a beautiful summer in DC and we decided to go for a walk by the White House and just enjoy the city. We talked and laughed and just enjoyed each other’s company. We had such a good time that we didn’t want the date to end.

So, he suggested that we grab drinks at the Sofitel (a luxury hotel). I agreed and we went to the bar and had a couple of drinks and began laughing and just enjoying the company again. There was no awkard conversation or long pauses that made me sigh and say “Well, I really should be getting back.” We just meshed well.

All in all I thought it was a great first/second date. I agreed to see him again. But, that didn’t last long.

My custody agreement made me unavailable for the week as I didn’t believe in sacrificing Munch’s time for a date with a man that I wasn’t in a relationship with so I had to postpone our next date for the following week. We spent the time talking on the phone and texting to build a friendship. No pressure.

Then one night in our sweet getting to know you conversations he tells me that he likes me. I smiled. I liked him too. He seemed nice. He then asked me “Are you dating anyone else?” I replied “Not at the moment.” He then asked me to not date anyone else.


Say what now? Don’t date anyone else? Why not? He told me that he only dates one woman at a time and prefers that women do the same. He explained how he used to date a woman for over 6 months. He would take her out, spend the night at her house and she would spend the night at his house. He had assumed that they were in a relationship only to find out that they had a friends with benefit situation.

He was crushed. He stated since that time, he wants to make sure that he has an exclusive opportunity to compete for a woman’s time and affection. He dated one woman at a time and wanted the same from the women he was dating. I was confused because we really didn’t know each other.

It was at that moment that I knew that we couldn’t go any further. He had lost his damned mind. I wasn’t her. I told him that. He was letting his insecurity about a woman not giving him her all show its head in our first/second date. You can’t let the choices of one decide the future for others, mainly me. He didn’t understand.

I was frustrated. I had to walk away. I explained to him how I saw things. I told him that the reality of the situation is that most relationships will flow the way they are supposed to flow when a man steps up. If you don’t want me to date other men, keep my attention and my time and then you don’t have to worry about it.

That’s what Mr. C did. He didn’t ask me to stop dating other men. He just filled up my time and my thoughts became about him. I wanted to get to know him. I wanted to spend time with him. I actually missed him when we were apart.

Process of elimination. Sometimes you have to do what you have to do to get what you want and the rest will take care of itself.


  1. I’m usually the insecure one! Lol. Actually I think I’ve improved a lot though. I was always paranoid my boyfriend or other guys would cheat on me. It would piss my boyfriend off! You have to trust who you’re with or else it won’t work out. I trust him a lot more than I used to. We’re kind of fighting right now so I just give him his space. He goes to nursing school. It’s really hard on our relationship sometimes because I want to see him but can’t. I do my own thing like go to the gym, spend time with my family, read, blog, etc. He’s taught me to trust and have your own life too.

    Liked by 4 people

  2. I totally agree! A lot of the flow does depend on a man stepping up. Funny thing is a few years ago if I had met a man like that I would have jumped for joy! Oh how exclusivity was so important to me back then! It’s still important but being exclusive doesn’t guarantee a relationship will work. Back then I thought it did. Now if a guy said that second or third date in I would label him as insecure/stalkerish, only bc in the past guys I’ve know that wanted to commit quickly were also controlling. Ohhhh these dating woes! πŸ™‚

    Liked by 3 people

    1. Lol. We became exclusive after two dates I think. We started a relationship quick and moved into an apt. fast. We’re not living together right now but it’s almost four years we’ve been together. It’s not easy all the time.

      Liked by 1 person

  3. Siiiiiiigh, I think we’ve all been there. This was the problem with my last, a bag man holding onto all those residuals then handing them off to me! Definitely should have been addressed before he took another go at dating anyone seriously.

    Liked by 2 people

  4. I feel like online dating has allowed me to somewhat figure out what I want in a relationship. πŸ™‚ Probably not actively looking for a relationship for the time being, but I hope I have enough confidence as you to say “no”.

    Liked by 1 person

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