As promised. . . my two worst dates

As mentioned in my last post, my two worst dates weren’t what most people would consider fun.

Before I tell you about these dates, I want to explain that “fun” for me is when I’m enjoying myself. And one of my definitions of “enjoyment” is when I get to learn something about me and others.

Worst Date #1

We emailed, talked on the telephone and decided to meet at one of my regular first time restaurants, a lovely Greek restaurant with a parking lot and vine covered arbor entrance in the back.

We arrived at the entrance at the same time and I said, “Hello I’m Christine” and the first words out of his mouth as he opened the door were, “Wow this would be a great place to meet someone for an affair.”

I’m not often left speechless but this did it. I was floored at his remark especially because it was the first thing. I thought, “What a jerky thing to say” and “Maybe I should just say I don’t want to have lunch with him” and “Wow he is certainly different then I expected” and “Oh my this is going to be a lllooonnnggg lunch.”

We were seated, made small talk, and looked at our menus. After we ordered I couldn’t stand it any longer and said, “I have to tell you that what you said when we first met made me feel really uncomfortable and concerned.”

He let out a huge breath and said, “I’ve been thinking what a jerk I was for saying that and couldn’t believe it came out of my mouth. And I’m embarrassed and thought you might just turn and go back to your car.” I told him I considered it. And asked what made him say it.

He explained he was so nervous to meet me because I was the first woman he dated since his divorce a year ago. He said his wife had had an affair and that’s why he got a divorce. As he talked, he began to relax and open up more. He said he had full custody of his children who were 8 and 10 and knew they were still pretty mad at their mother for leaving.

I knew I wasn’t attracted to him and wasn’t interested in dating him, so that made it easier to have a frank conversation with him. I asked if he would like some advice and when he said yes, I told him I thought his children needed him to stay home and raise them. And it would be good for him and his children to see a therapist to help everyone heal from the marriage/divorce. He agreed this was a good plan and said it took the pressure off him to start dating right now.

The fun part was:

  1. He turned out to be a lovely man.
  2. Lunch was enjoyable.
  3. I left feeling good about him and men in general.
  4. He thanked me for being so honest and encouraging him to be a full-time dad right now.

Worst Date #2

We emailed, talked and met at a restaurant (different restaurant). He was there when I walked in. He introduced himself and we were seated. He was 48, 6’1”, dark hair and ruggedly handsome (just like his picture). As we were looking at our menus I noticed his menu was shaking – a lot. I wondered if he was sick or handicapped or …..

So, after the waitress took our order and we talked about a few “get acquainted” subjects, I finally asked him why he was shaking.

And he said, “I didn’t tell my mother I was going out and I think she might be mad.”

I said, “Excuse me?”

He said, “I live with my mother and she gets concerned if I don’t tell her when I leave where I’m going, who I’m going with and when I’ll be back.”

Trying to give him the benefit of the doubt, I asked, “Is she dependent upon your care?” He said no. OMG!

He went on to explain he thinks his mother would really like me and he’s looking forward to introducing me. OMG again!

I told him thank you for the nice compliment and that I didn’t think we had enough in common and I didn’t see a future for us.

The fun part was:

  1. I added to my list of questions, “Do they live with anyone?”
  2. I have told this story so many times and I love the reactions of my audience.
  3. Not the first or last time I learned you definitely can’t judge someone by their looks.

So, you get to decide what attainable “fun” is for you. And writing it down may help you find fun where others don’t. Every date can be fun, entertaining and a good learning experience.

How about you? Do you have a “worst” date to share?

~ Christine
Dating and Relationship Expert

Goal Setting + Purposeful Dating = Satisfying Relationships


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