First, Pie, a 58-year-old self-admitted cougar, has been dating 24-year-old Oleg for four months -- and her best friend, Terese, strongly disapproves. Could Pie be headed for heartbreak? Next, Forty-year-old Sanjay is a wealthy cosmetic surgeon who met 18-year-old Jacqueline on a dating website. They’ve only been together for four months and are already talking marriage. Sanjay’s friend, Mike, is convinced that Jacqueline will put him right in the poorhouse! Then, Sixty-two-year-old Bill and his 23-year-old girlfriend, Bri say not only do they come from two different worlds, but they have a 39-year age gap and are at different stages of their lives. While Bill and Bri have been together for four years, they say they are at a crossroads. Next, Brenda says she fell in love with and married her husband, Don – despite their 26-year age gap. But soon after, she claims her “Prince Charming” turned “crazy” and “temperamental.” Is their age difference at the root of their issues? Finally, Joni claims that Gina used to be one of her besties but says all that changed when 23- year-old Gina began dating Joni’s 49-year-old father, David, behind her back and giving birth to David’s child. Can Dr. Phil help this father and daughter fix their relationship? Chapters: 00:00 - 58-Year-Old Cougar Dating 24-Year-Old From episode 13057 The Cougar Controversy: Older Women Dating Younger Men 13:26 - Couple Met On Sugar Daddies Dot com From episode 5010 Cougars And Sugar Daddies 26:13 Rich 62-Year-Old Dating 24-Year-Old From episode 19088 ‘Marrying Millions: He’s 62, She’s 23’ 40:17 26 Year Age Gap Couple Can’t Stop Fighting From episode 14059 The Pain Of Marriage Remorse: I’m Ready To Leave My Husband Who Is 26 Years Older 54:12 Woman Has Child with Her Best Friend’s Dad From episode 19024 ‘My 49-Year-Old Dad is Dating My 23-Year-Old Friend’ #agegap #relationship #drphil Top 5 Spoiled and Entitled Kids | Compilation | Dr. Phil https://youtu.be/fH1sTdF6jyg The Dr. Phil Show was an American daytime talk show and TV series with host and personality Dr. Phil McGraw, who offered advice from his experience as a psychologist. New episodes of the Dr. Phil Show aired every weekday on CBS from 2002 to 2023 and was created by show runner Oprah Winfrey. The show provided the most comprehensive forum on mental health issues in the history of television. For over a decade, Dr. McGraw used the show's platform to make psychology accessible to the general public by addressing important personal and social issues. Here on the Dr. Phil YouTube channel, you will find the best moments, highlights, and full episodes from the TV show.