27, Dating A 53 Year Old

This week's caller met her husband while working on a cruise ship. She's got plenty of stories about life behind the scenes at sea: from a painful breakup that sent her into the world to finding love, to building a new life in California, and lots of cruise talk in between. Plus, ...  Show more

This week's caller works in video games. The first half of the call gets into the current state of the industry and what it's like building a career in something you love. Halfway through, this caller earns a spot on one of our favorite unofficial Beautiful/Anonymous lists: peopl ...  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 ...