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Postmarked & Tipsy

Jessica and Kara

What can a postcard really tell you?

On Postmarked & Tipsy, we explore real vintage postcards from the past — and the stories hidden between the lines.

Each episode starts with a simple message… and quickly turns into something else:

A mysteryA questionOr a story that doesn’t quite add up

With a drink in hand, we dig into the details, the history, and the people behind the postcard — trying to ... more

PublishesDailyEpisodes15Founded3 months ago
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Society & CultureHistory

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Latest Episodes

This week’s postcards spiral quickly from “I need medicine” into wartime anxiety, mysterious boxes, diphtheria, and one deeply unsettling Christmas message.

In this episode:

- A desperate 1940 postcard from Kansas City

- The least festive Christmas... more

A century ago, an 18-year-old Massachusetts National Guardsman boarded a train bound for the Mexican border.

At every stop along the journey, he mailed a postcard home.

More than 100 years later, those postcards survived.

In this special interview... more

YouTube

A postcard from 1935.

A mysterious message.

A motorcycle insult.

And someone named Helen caught in the middle.

In this episode of Postmarked & Tipsy, Kara and Jessica unpack a bizarre vintage postcard sent from Syracuse, New York during the Great... more

YouTube

To our listeners - this is an episode best seen and heard because of the Boston 2026 World Expo visuals - head over to our YouTube Channel to watch it: www.youtube.com/@PostmarkedTipsy

A few months ago, we were sitting in a Rhode Island tave... more

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In this episode of Postmarked & Tipsy™, we sit down with postcard historian, collector and educator Kathy Alpert to explore the strange, funny and unexpectedly emotional world of vintage postcards.

What started as a conversation about postcards quic... more

YouTube

Leading up to the Boston 2026 World Expo, we sat down with longtime broadcaster and former American Philatelic Society leader Lloyd De Vries to learn more about the fascinating world of postcards, stamps, postal history and collecting.

We talk about... more

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"I feel sorry for all you have to do… and no car to get around.” These postcards were sent to our guest’s family — and immediately raised questions.

In this special guest episode of Postmarked & Tipsy, we’re joined by The Gallivanting Ginger, who ex... more

YouTube

We had questions about National Postcard Week… so we asked one of the organizers.

In this episode of Postmarked & Tipsy, we talk with Raina van Setter about the history of National Postcard Week, what people actually do during it, and why postcards ... more

YouTube

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Postmarked & Tipsy launched 3 months ago and published 15 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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