Jack, relives a volatile relationship with a younger woman - Buddie, a woman with a world class resting bitch face, strong opinions, and a volatile temper. Sounds like fun, sign me up! --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

Everyone has those people who come into their lives and forever change you for the better. For Jack, one of these pivotal people is a woman named Shania.  --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

In a rare twofer, Jack relives a 2 stories of fuckery from his past... The Fergie Foursome, and Rodan, the nanny that never was. --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

Listening to that little voice in the back of his head, leads to Jack running into the one that got away... The White Whale.  --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

Jack receives a DM from SFB, a woman from high school.  Now that her marriage is falling apart, she's looking to take things to a new level. What could go wrong?  --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

Jack describes a relationship in real time as it blows up with Mumbles - a woman with a few too many entanglements.  --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

In this installment, Jack relives his brief long distance relationship, with Toto. A cross country road trip puts this young relationship to the test.  --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

Jack retells the signs from beyond that he received after his father passes, and how he spreads his father's ashes with help from the other side.  --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

Jack ventures into the world of opera, only to have the fat lady sing before he can make beautiful music with Figaro.  --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support

Right before the pandemic hits, Jack hits it off with the GTA. While trying to navigate dating during a pandemic, and a deal with this woman's baggage, it proves to be too much for this young connection to last.  --- This episode is sponsored by · Anchor: The easiest way to make a podcast. https://anchor.fm/app --- Send in a voice message: https://anchor.fm/theredflags/message Support this podcast: https://anchor.fm/theredflags/support