Dating Disasters

The world of man-kind can be glad that my dating days are over. I was the worst girl to date. If a guy made one comment that I took the wrong way, then I would switch off mentally, stop making any effort, the conversation would dry up and I would start hoping my phone would ping or ring, this giving me an excuse to leave early.

Maybe it is wrong. but in the world I grew up in, all I had to do was look good to be ensured with a steady flow of interested men. I had a boyfriend throughout my late teens and early twenties, and so it was only as I approached my mid-twenties that I started to date men that I hardly knew. It was awful in many ways. As I look back, I know it is probably because I was not ready to be dating someone else. I was unsettled within myself. I didn’t understand me, and I had no idea what I was looking for in a man. I suppose I just hoped a miracle would happen and I would recognise Mr Right while sharing a bottle of wine with him.

The problem seemed to be that no matter what a man looked like, I judged him on the words that came out of his mouth. Sometimes the mood I was already in made it worse for him. If a comment seemed presumptuous, overly familiar, overtly flirtatious, or…well, to be honest the poor guys I dated probably had no clue why I suddenly went frosty on them. I should never have been out on a date with them to begin with. I did not want any of them really. I was in a stage of life when I was lost, and dating was a stupid idea. I was to blame.

Yet I dated a lot of men. Most dates were one-offs. Something they said put me off, and I decided that it was a no. Some men passed the first date stage. I remember some men I had multiple dates with. I even made out with some of them. But there was no sex with any of them. Not one. That was my choice.

I learnt towards the end of that disastrous dating stage in my life to be honest with the handful of men who dated me enough times to assume they should expect me to take a tumble with them. I realized I had to tell them what I had come to understand about myself, “I’m just not ready. I’m messed up at the moment. I am so grateful that you have been willing to spend some time getting to know me, but I don’t think this can work because I am deeply depressed and I am not enjoying life. That’s not your problem, but you need to be aware that I am not ready for anything more than meeting for drinks or a meal right now.”

I said something like that to a guy named Benedict who I had been going out with for a month already. Only Benedict surprised me. It turned out he understood depression very well. He was very kind and empathetic. He was also very generous. After that he really thought more about our dates. He took me to some special places and events.

The problem again was his occasional comments that totally put me off developing romantic feelings for him – he could be such an opinionated, arrogant know-it-all! But I truly appreciated his friendship. I think neither Benedict nor myself had any desire to have anything more than a platonic friendship after a handful of dates.

As it turns out….there was a happy ending to our time together. You see Benedict’s boss was….Ben. Yes, that’s right, my Ben! Not only did Benedict only have praise for his boss (which is unusual in itself) but I later learnt that Benedict had twigged that Ben had been impressed by me, and when informing Ben that there was no romance at all between himself and I, Benedict cleared up a few misperceptions Ben seemed to have about me. Ben’s brother had contributed to that. (I went on two dates with Ben’s brother.) Yes, yes, I may have dated most single guys in Chicago, but I was not a man-eater. Not long after that…I moved away. I moved far away. I moved to London in England and there….I got close to Greg much closer than I should ever have allowed myself to get.

You see…Greg had all the right words, he never made a comment that I took offense to. Yet ironically it was the smooth talker that left me more damaged than any other relationship or dating disaster. He talked his way into my bed and then had nothing to say to me when he realized I was suffering with depression.

What do I think of Greg? No comment!

I feel bad when I think of all those men I dated who I was overly picky with. Some of them may have been great guys. I don’t remember much about any of them now. They all blur into hazy memories. I cannot remember the comments they made that I took exception to. I do remember my feelings though. It was a time when I was a hazardous material. I just was not ready to be dating.

8 replies on “Dating Disasters”

I think all those dating experiences have led you to Ben, because you got to know yourself better, and despite your depression, also learned what you want from a relationship. I have some dating disasters in my life too…
~ Marie xox

Liked by 1 person

I’ve never actually dated like that before. I usually start with talking online and if it gets to the meetup stage, it turns into a relationship pretty quickly. It’s partly because, like you, I am extremely picky. I generally determine initial compatibility from the things they say. I made the mistake of entertaining one who talked a good game online, but in person, became a total Greg and kept playing “anything you can do I can do better.” He was gone pretty quick. I hope one day I can find my “Ben.” 🙂


Back in the day when I was dating – which is around ten years ago…I was way to scared to connect with strangers online. Chicago is a lively enough city without searching dating sites!!! I had a lot of dates with friends of friends….or cousins of friends….or colleagues of friends. There were a handful who I just met at parties or events and they asked me for my number and I agreed to a date.

But you know….I was not ready….I was not really over my first boyfriend….I did not know who I was yet, or where I was going in life….I was experiencing depression for the first time in my life and all those men – they did not understand that.

I am trying to convince Ben to let me clone him – he is such a find!!!


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