Making people laugh is an important social skill and it can't hurt to have some good jokes in one's repertoire. Sometimes I have told jokes and people have thought I was being serious and concluded that I was strange. This happens with people who don't know me and who I am just getting to know so I've learned to be careful with my humor when I am just getting to know someone. In dating situations people are often worried about meeting someone abnormal and if they think one is serious when one tells a joke that may be an early end of what might have been a beautiful relationship.
Women like men who make them laugh. On the other hand sexual jokes can be offensive to women especially ones that appear to be disrespectful. A friend of mine once asked me to post his picture so a girl he was corresponding with from a dating site could see it. The girl had already posted her picture and she was very beautiful. One of the pictures he had was of himself with two beautiful women. I suggested to him that I post that picture since it would be funny. I show the picture below with his face erased (but the same expression) so as to protect his privacy. We posted the picture with a joke asking her to save him from these women.
A female friend of ours saw that we were posting the picture and told us that if she saw that picture she would never get in touch with the guy who posted it. She said she would think he's a pig. She said he should instead show a picture of himself patting a dog or playing with kids. So at least in her case this attempt at humor would have led to failure. On the other a week after this picture was posted my friend got a response from the woman he posted it for.
I read an article woman from Texas named Gail who came to a singles party in Washington D.C. with her friend (whose name was also Gail). Gail wrote"
At the door, one fellow, noticing my Western attire and silver star pin, asked if I was the sheriff. Then he turned around, spread out his arms and said, "Frisk me!" Gail and I quickly rode off into the sunset for the other party.
This is a great example of women not appreciating sexual humor.
I think that both the man who was trying to be funny and the woman who was turned off by it made a mistake. Gail interpreted the man's humor as a sign he was a jerk instead of appreciating that he had a sense of humor and so lost an opportunity to get to know someone who might have been fun to be with.
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