A man recounts losing his virginity at 16 to a much older woman who may or may not have been a prostitute in a Ramada hotel room on New Year's Eve Eve of the Millennium.
The speaker expresses regret and jealousy towards his partner and compares his behavior to that of other men who cheat; he also expresses frustration with the lack of excitement in his relationship.
A conversation about acting turns into a contemplation on retirement for Bert Kreischer who jokes about signing up for four more "machine movies" before leaving acting for good.
The speaker tells a story about visiting a quirky screenwriter's house, arriving sweaty and smelly with a bag of clothes and finding the writer cooking in the kitchen.
The Dr. John Alexander's Sigma male blog is full of bad relationship advice and reminds the speaker of male inspiration Instagram pages.