I picked this up based on the title. I thought it seemed like an interesting premise. From reading the introduction, we find out that the author has experience in standup comedy, has written and produced for several TV shows and is a dating columnist. I had never heard of him before picking up the book.
I found the title and the introduction to be deceptive. He went on 500 dates but he admits he is only going to talk about 50 of them. Those are covered by two to three page essays in section one. There were several problems for me. One was that I don't think he struck the mix of serious and funny. He would be recounting a date and indicate that he said something but based on everything else he wrote you knew he hadn't actually said it. On the other hand, he had been serious up to that point so the flippant thing he said ruined the serious part.
The second section is his observations on dating and romance and the third section is dating fantasies. Some of it was amusing but overall it was pretty unoriginal.
The fourth section is fake news stories he wrote about romance, dating, and the sexes. This was the funniest section to me.
As an overall impression, I would say that I cracked a smile a few times but overall I did not think it was insightful or very funny. It may be somewhat insightful or funny to people who are not experienced in dating or have not heard all the clichés relating to dating and romance.
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