Wednesday, March 4, 2020

My Worst Dating Mistakes

Everyone makes mistakes.   Here is a list of the worst times I screwed up while dating.  Please learn from my bonehead mistakes.


1) When I was a teenager I discovered some soft-core porn written by a famous author.   Think "50 Shades of Gray", but written by a real author rather, so it was actually pretty good.   When I purchased the second book at a book store (how we purchased books before the internet), the female clerk very pleasantly asked about the book.

I froze like a deer in headlights.  I stuttered something stupid, paid and ran faster than the deer.

Never be embarrassed about something you like - even if it's porn.  Don't let embarrassment affect your behavior.  You don't have to tell everyone everything, but if someone finds out, brave it out and see what happens.  Who knows, I might have ended up acting out scenes from the book with the young lady.



2) Once I went dancing and met this beautiful woman and I had my hopes up till she opened her mouth.  Out came the most high pitched, annoying voice I had heard, worse than Fran Drescher's "The Nanny" voice.  So I ignroed her and moved on.

Big mistake.   There must have been countless men that overlooked that gorgeous woman.   Her voice was what kept her single, and any truly intelligent man knows no one is perfect.    I should have snatched her up and held on.  Ignoring a woman because of a minor imperfection was truly stupid on my part.


3)  On two different occasions, I promised a woman that no sex would take place on our first date.  I wanted a relationship, not a one night stand.   In both cases we fooled around a lot and I am 99% sure the women in question wanted me to break my promise.  One took me to her bedroom and the other physically attempted to do the deed.   But I kept that stupid promise and left before things "got out of hand".

I never got a second date with either of them.  I should have communicated much better, at least asking her if she wanted me to break my promise.   But I also could have never made that promise in the first place or put in a caveat  ('...unless you honestly asked me to.').  Some women like to affect they are less interested in sex than they really are.  Do not do the same.


4) In my twenties  found an incredible woman who said all the right things about kinky sex.  On the first intimate date I did exactly what we discussed and I enjoyed it but she was quiet.  I thought she did not enjoy the sex.  I felt that she had lied about what she desired.  So I broke up with her.  Turns out she had enjoyed it and was just naturally quiet.  That was really just the first mistake I made.  The more important one was when she sent me an angry email clearly implying she had enjoyed the sex, I did not apologize and ask her to take me back.  My pride destroyed what could have been a great relationship.



5) In my forties I met a very nice Japanese woman.  Unfortunately she moved back to Japan.  I promised to stay in contact, but I failed to do so.  Later I learned she was interested in me and I could have turned it into something.
Long distance relationships are hard, but they are better than no relationship.  I should have stayed in touch.


6)  My worst night ever.   I found a bar that advertised dancing.  I went their and found it was small and not that crowded.  There were a group dancing in the back that included 3 young woman - a blonde, and two brunettes.   The blonde was gorgeous.  I was still trying to come up with the perfect line and the right time to deliver speak to the blonde when one of the brunettes came over.

She was slightly drunk and asked me "Are you a dirty boy?" 

Unsure of what she said, I said "huh?"

She replied again "Are you a dirty boy?"

Her tone was weird - halfway between a come on and an insult.  So I had no idea whether this was the opening line for a XXX movie or a feminine empowerment movie.

I went with my desire rather than logic and said "Yes."

Wrong choice.  Boy was that the wrong choice.  She went off on me like I had tried to slip her a rufie - talking about how her boyfriend was going to kill me etc. etc.  I have blocked out most of what she actually said, but I left the bar crying.

Did not ask another woman out for months.  Worst part was I had barely noticed her, the blonde out-shown her by a mile.

THE WORST LINE DELIVERED NOW IS BETTER THAN THE BEST LINE 2 SECONDS LATER!

The best time is right when you see her.   Your best line is not worth anything except as a joke.   Don't wait, say hello.