27, Dating A 53 Year Old

This week's caller is an avid kayaker with a Friday night all to himself. He tries not to make this episode about kayaking, but come on, when you're this passionate about something, it's going to show up. If you're not into kayaking, don't worry. This one's also about being lonel ... Show More

As Beautiful/Anonymous kicks off its tenth year, Gethard talks with a mail carrier turned artist who's done settling and ready to take some big swings, following a plan that might take you a minute to wrap your head around. She and Geth talk old jobs, new goals, and why betting o ... Show More

As the year turns, Gethard keeps the tradition alive by talking with callers two minutes at a time about their hopes for 2026. We hear from familiar voices and first-time callers alike, all checking in with what they're reaching for in the year ahead. New jobs and new hobbies, hi ... Show More

<p>Why should you date an older woman if you want to be successful?  Why does dating younger women or being single and on the prowl often keep young men from being as wealthy as they could be?  Dating/relationship expert Lucia discusses the many benefits of dating older women.</p ... Show More

In Episode 3, I speak about the benefits and challenges of dating someone older/younger than yourself. I dive deep into the psychology behind age attraction and explain what older/younger age signals to potential partners. Having a relationship with someone much older (>10 years) ... Show More

Oh, age is nothing but a number. Many single women from 28 to 40 tell me this. But why do so many women but so few men repeat that nonsensical phrase—oh, age is nothing but a number? If age is nothing but a meaningless number, why do most news stories and feature articles about p ... Show More

The guys talk about the issues faced by men in their 30's. 

Isabel LaRosa is a 18-year-old singer, songwriter, and video director from Annapolis, Maryland. She started writing songs at the age of 12 and began releasing her music online in 2021. Her song "Older" went viral on TikTok in early 2023, and has since accumulated million of views ... Show More

On this week’s episode, we talk all things dating in your 30s!Are you compatible or is it just chemistry?How to approach dating apps in your 30sCreating an honest dating profileLaura’s sexual experience with Star Wars  Show notes:Unhinged and Bumbled up podcast - https://shows.ac ... Show More

I’m really over here trying to figure out why 30/40 year olds gossip about people in their 20’s 🤔 

Men have been dating younger women forever – no one questioned Hugh Hefner. So why is it when women do the same we hate it? And it’s not women who hate her relationship – it’s men! Produced by Dear Media. See Privacy Policy at https://art19.com/privacy and California Privacy Noti ... 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