27, Dating A 53 Year Old

A sixth-degree black belt calls from a hacker convention to talk ham radio, phone phreaking, off-grid networks, hacking E-ZPass (fine, theoretically), and whether Chinese and Russian hackers already know your mom's maiden name. Sign up for Beautiful/Anonymous+ to get ad free epis ...  Show more

This week's caller has a full-time job, a toddler, and somehow also helps run an anime convention in their spare (lol) time. Gethard gets a crash-course in anime as he talks with our caller about what happens when the thing you love starts becoming a whole lot of work. Plus, an e ...  Show more

Dear Steve and Shirley, I am a 33-year-old woman and I recently started dating a 25-year-old man. The age difference really didn’t bother me at first but I am starting to notice that he seems to be a little bit inexperienced when it comes to sex. The first time we got together th ...  Show more

Dear Steve and Shirley, I am a 28 year old woman and I’ve been having bad luck on the dating scene. Finally, I met someone and thought he was great. Emotionally, he fulfilled my needs and he planned the best dates. We formed a bond over the fact that we were both tired of dating ...  Show more

We react to the article “The Case for Marrying an Older Man” by Grazie Sophia Christie, a controversial take from a younger woman who pursued an older husband as a shortcut to her dream life.Topics covered:-As a woman, is your greatest asset your youth?-Power differences in age g ...  Show more

Dear Steve and Shirley, I’m a 29 year old woman and my fiancé is 30. We met at a house party four years ago and we got engaged a few weeks ago. We started out as friends for a while because of his height… He is shorter than the men I used to d ...