Jack and Cathy
The Jack and Cathy (Shit) Show
Hey, it's Jack and Cathy, and welcome to our Shit Show. We give you a front-row seat to the roller coaster of love. Marriage. Divorce. Starting again. Finding each other when it seemed impossible. Ever wonder what happens after the dating frenzy? We spill the beans on navigating relationships - the good, the bad, and the hilarious. Join us for real talk, anecdotes, and lessons on keeping the flame alive in the second act. It's not just a podcast; it's a guide to making love last. Subscribe for a laugh and some practical tips on thriving in the messy, beautiful world of lasting love.
Author
Jack and Cathy
Category
Podcast website
Latest episode
Jun 18, 2026
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Episodes
EPISODE 108: The End of Season 3 (Listener Questions) 01.01.2025 1:11:44
In this episode … Jack and Cathy spend a few minutes sharing their desires to remain fit and, in the process, took on some new fitness routines like playing basketball - against one another! And then it’s on to the Year End Questions from the Shit Show Fans, now formally known as ShitHeads. Happy New Year, everyone. Here’s to a great 2025. Recorded December 31, 2024
EPISODE 107: The Holidays: The Worst of Us (Happens to Everyone this Time of Year) 24.12.2024 1:06:39
In this episode … Jack and Cathy lift up the happiness factor by talking about how the Holidays can expose the worst parts of our relationships. Yep, deep end of the pool stuff to ring in the Christmas season. Yes. Merry Christmas. Recorded December 23, 2024
EPISODE 106: The Holidays: Surprise Christmas Questions 20.12.2024 1:03:59
In this episode … Jack and Cathy enjoy a great holiday party, get dolled up and then record this podcast, only to realize the video camera wasn’t working properly. So it’s mostly audio this time around. The two share Christmas memories and stories as they get closer to celebrating the big day. Recorded December 16, 2024
EPISODE 105: The Holidays , Movie Edition 13.12.2024 42:00
In this episode … We jump right in discussing our favorite Holiday Movies. As is expected, Jack’s list includes a rom-com of sorts and Cathy’s list includes some all time classics. Chime in to the comments with your favorite Holiday movies. (and Happy Birthday to Mom and Sam) Recorded December 11, 2024
EPISODE 104: The Friends that Come and Go 03.12.2024 54:21
In this episode … Statistics show that after 35 years old, we have earned most of the friends we will ever know in life. That making new friends as we age becomes increasingly difficult. We have both lost several friends in our lifetime - some by design, others because of the fragility of life. We also know that our relationship is built on a solid foundation of friends and this luck is never lost...
EPISODE 103: The Challenge of the Holidays 25.11.2024 53:14
In this episode … Everyone knows the Holidays can present all types of challenges. As many older parents know, once the kids leave the nest, seeing them is less frequent and the holidays only makes missing them even greater. This year, we’ve struggled a bit trying to make peace with the fact that seeing our kids less often is a bummer and scheduling time to see them all can be challenging. Cathy...
EPISODE 102: The Interview with Justin and Haley, Founders of the Price of Avocado Toast 20.11.2024 55:52
In this episode … Hot damn we can’t stop talking about money! Social media has its good and bad. In this situation, Social Media introduced us to Justin and Haley, financial advisors and founders of the Price of Avocado Toast podcast and website. After interacting with some of their posts on Threads, Jack reached out and asked them to be on our podcast … and silly them, THEY AGREED. This is a w...
EPISODE 101: The Hard Conversation About Money 14.11.2024 51:40
In this episode … As you get older, money habits are either good or bad. While we still have several viable work years ahead of us, odds are that our age might affect our earning potential in the next few years. We are both 58. The Motley Fool website recently posted this: “It was not surprising that 77% of retirees used Social Security as a source of retirement income, and 92% of those over 65...
EPISODE 100: The Reality of Politics and Dating in 2024 05.11.2024 1:16:40
In this episode … Cathy loves our banter at the beginning of each episode and in this particular moment she wants to dive head-first into our disagreement on Wordle. But then we get into the meat of the podcast. Dating is hard enough, especially as we get older. With Red State / Blue State thinking, finding a mate becomes even more difficult. Never before in our lifetime was politics such a divi...
EPISODE 99: The Inevitable Life Changes 28.10.2024 52:04
In this episode … First, we have a beef with Kara Swisher and Scott Galloway for “stealing” or creative podcast introduction of talking first before then moving to our intro … as if this is actually something to be stolen. Still, it seems very interesting that we’ve been writing them and then suddenly their podcast intro resembles ours. Coincidence? Hmmmm … Many changes in life happen at a mome...
EPISODE 98: The Honeymoon 22.10.2024 52:13
In this episode … Well, we are now married. After meeting 3 1/2 years ago on a dating app, we’ve closed the deal. And of course, there’s the honeymoon and consummation of our love and commitment (SMH). A trip to the UK visiting London, Bristol (to be with family) and Scotland (Edinburgh) was simply amazing. We travel quite well together (always have and it’s one of our commonalities) because we...
EPISODE 97: The Wedding 07.10.2024 54:07
In this episode ... We got married over the weekend. Three years after meeting online, here we are. Married. The ceremony and dinner was with family and friends. It was all amazing. We are both the luckiest people in the world. Recorded 10/07/2024
EPISODE 96: The Craziness of Our Upcoming Marriage 29.09.2024 1:05:42
In this episode … We re-hash our “Secret” conversation form the last episode, an episode we didn’t want to produce. And then we dive into how stunned we are to be getting married in one week. Were we lucky? Were we active in the dating seen to increase chances? Were we completely self-aware and unrelenting in our pursuit of what we wanted? Who knows. Maybe all of the above. But here we are, one...
EPISODE 95: The Secret and Cathy 26.09.2024 48:08
In this episode ... Cathy admits to living in a place where fear of the future (mostly money) negatively affects her. Living in "lack" means staying in lack. So Jack suggests they watch The Secret so that Cathy can better understand her reaction to life's events. Be warned ... Jack talks A LOT in this episode. And Cathy feels great, too. Recorded Sep
EPISODE 94: The Challenge of Parenting Adult Children 10.09.2024 56:57
In this episode … During dinner with good friends, we talked about the challenges of parenting adult children. Or perhaps a better way to describe our conversation might be this: how do you push the kids out of the proverbial nest without bracing their potential fall. We all hope, as parents, that we’ve done a ton of work preparing our children for adulthood. Still, we often want to protect and...
EPISODE 93: The Start of the NFL Season and More 05.09.2024 52:36
In this episode ... Last year, we made a bet regarding the Bears and the Packers. Cathy, a Packers' fan, won the bet and Jack has yet to pay up. And he tries his best to walk back from the money he owes. Plus, there's plenty of talk about relationships, the wedding and more. Recorded September 4, 2024
EPISODE 92: The Overnight Stay with the Grandson 27.08.2024 44:17
We had the chance to watch our new grandson for an overnight stay (sorta) - Mom and Dad showed up late in the morning after being at a wedding). Jack spent a few moments alone on long walks with the new edition romanticizing the evening only to have reality slap him in the face. Recorded 08/26/2024
EPISODE 91: The People We Don’t Like 20.08.2024 45:39
In this episode … We discuss people that drive us crazy. Actually, people that drive JACK crazy. Every once in a while other people can frustrate us. So be kind to everyone and remember (and embrace) that we live in a shared world. Recorded 08/19/2024
EPISODE 90: The Baby, the Movies, the Follow-up with Linda and More 14.08.2024 46:50
In this episode … We met with Linda (per our last Episode) and learned a bit more about one another. We also ramble on a bit about the new grand baby and movies … because of course there’s a connection between the two! Recorded 08/12/2024
EPISODE 89: The Road is Not Always Rosy 06.08.2024 53:10
In this episode … Between podcast episodes, we talked of how we don’t often share the challenges we face in our relationship. Maybe we need to be a bit more vulnerable with our life stories rather than only talking of house remodels and new babies. So Cathy decided it was time to share a tough few days we had after not listening to each other very well. Recorded 08/05/2024
EPISODE 88: The Birth of a Grandchild 30.07.2024 48:11
In this episode ... Jack's daughter and son-in-law welcome their first child and the first grandchild for everyone. The excitement is through the roof. But before we appropriately indulge in discussions about the newborn, Cathy learns a bit about the "Hawk Tuah" girl ... Recorded July 29, 2024
EPISODE 87: The Love for Tequila and Other Nonsense 23.07.2024 47:24
In this episode ... Our love of tequila comes out front and center to get things started. Perhaps we have a problem? We dive into plans for the wedding, Joe Biden stepping down and possible sponsorships. Simply, a mishmash of nothingness. That's podcasts, right? Right? Recorded July 23, 2024
EPISODE 86: The Wedding Plans and a Question for the Listeners 15.07.2024 59:43
In this episode … It’s rare - if ever - that we ask for listeners to provide their point of view on a topic. Yet here we are. We are getting married in a few months. To be sure, as with any wedding, the day is important to us but it’s not everything. It’s a day in our relationship. But we are realizing for others it has a larger significance. That’s why we ask for listeners to provide their poin...
EPISODE 85: The Meeting of Other Divorcees 03.07.2024 51:48
In this episode ... We met a few other couples whose life stories matched almost identically to ours: All divorced after long marriages, struggles post the divorce and finally settling in to a life of peace boosted by a second marriage. We were surprised how much this meeting impacted us and so we turned it into podcast. Recorded July 2, 2024
EPISODE 84: The "All-Over-the-Place" Discussion 25.06.2024 44:23
In this episode ... We are all over the place and finally able to enjoy each other more and more since we chose to put home projects on-hold until after the wedding. Now that we have more time, we have more stories to share and laugh about. Our new friends Pam and Dirt Road Randy came up to Milwaukee with their friends Max (Walt?) and Dorris to enjoy some Summerfest vibes ... And so much more. Rec...
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