The Planner’s Passport - Wedding Planners, Travel Agents, Decades of Stories
Join Jen and Megan every week as they spill the tea on over a decade of wedding planning adventures, share their journey into the travel business, and dish out advice on living your best life. Based in the Midwest, these two professional wedding consultants and travel gurus have been kindred spirits since the late ’90s and are ready to bring you inside the crazy world of weddings sharing hilarious stories of things they have witnessed, lessons they have learned and a few tips along the way for vendors, brides, grooms, moms, dads and honeymooners alike! Tune in to hear these two peas in separate pods give you a behind-the-scenes look at their lives as wedding planners, discuss the ins and outs of being small business owners, and hopefully inspire you to break out of your routine and explore the world. Megan’s Businesses Include: Dare to Dream Travel - Booking Sandals and Beaches vacations, honeymoons and family travel / @dtdtravelwi Dare to Dream Weddings - Wedding Planning Services in Milwaukee, Wisconsin / @dtdweddingswi Jen’s Businesses Include: A Fresh Event Travel - Wedding Planning Services in Chicago, Illinois / @afresheventco We Roam Solo - Travel planning services for Solo Travelers Worldwide / @weroamsolo
Episodes
This week on The Planner’s Passport we’re joined by a very special guest, Grace from Tarot D’Amore.
Grace is a soulful tarot and movement specialist who brings wisdom, intuition, and heart to everything she does. She offers tarot readings for weddings and beyond, guiding people to connect with themselves, their relationships, and the deeper meaning behind life’s milestones.
In this episode, she shares her story, how she began blend...
It’s one of the questions we get asked the most, and this week we’re finally talking about it. After years of watching couples up close on one of the biggest days of their lives, we’ve seen just about everything—moments that melted our hearts, and a few that made us quietly wonder how the night (or the marriage) would end.
In this episode, we’re sharing some of the stories that stuck with us, the red flags we’ve noticed along...
We love a confident couple who says, “We’ll totally have time!” … until they realize photos, champagne, and nerves say otherwise.
In this episode of The Planner’s Passport, we’re diving into one of the biggest wedding day struggles — the timeline. We’re breaking down why you’re probably not giving yourself nearly enough time, how long things actually take, and why your vendors aren’t being dramatic when they say that dinner is goin...
The wedding industry is, at the end of the day, a for-profit industry. That might surprise some couples, but it’s true. This week, Megan and Jen are pulling back the curtain on how pricing works in the wedding world and why it makes sense.
Here’s the thing: just because you’re planning a wedding doesn’t mean vendors should automatically discount their services. Yes, weddings are joyful, and yes, we’re thrilled to celebrate with yo...
After years of planning weddings and events, Megan and Jen have figured out which rules matter most and they are not budging. In this episode, they dive into the non-negotiables of wedding planning: the details that make or break an event, the mistakes couples should avoid, and the standards they will always defend. If you are planning a wedding and wondering what is really worth it (and what is not), this episode is packed with ho...
This week, travel talk is back as Megan takes us on a journey back to Jamaica
Join us as she shares her family vacation to Beaches Negril on the famous Seven Mile Beach, one of the top all-inclusive resorts in Jamaica. From stunning Caribbean beaches and unforgettable sunset views to unexpected travel mishaps and family adventures, this trip had it all. We talk about Beaches handled the bumps with care, why going with the flow is k...
This week we’re diving into one of the biggest wedding guest debates: kids or no kids? We break down the pros and cons of having little ones at your wedding, how to figure out if your kids are actually invited, and what you should do (and plan for) if you decide to make your wedding kid-free. Whether you’re planning your own wedding or packing up the stroller for someone else’s big day, this episode has the tips, stories, and advic...
This week, we’re talking about the one thing you can’t control on your wedding day: the weather. From sudden storms to sweltering heat, we’ve seen it all—and we’re sharing our own weather disaster stories to prove it.
We’ll cover what couples often forget when planning for outdoor ceremonies and receptions, why guest comfort should always come first (hint: no one wants to sit in 90-degree heat), and the practical steps you can take...
Ever wonder what really goes on behind the scenes of a wedding? In this laugh-out-loud episode, two seasoned wedding planners spill the tea (and maybe a little champagne) on some of their most outrageous confessions from the job.
From sneaking sips of prosecco during the ceremony to shamelessly devouring the couple's untouched appetizers (look, someone had to eat them), no story is off-limits. Oh — and yes, one of us definitely had...
This week, we talk about… well, everything and nothing at all, which is basically our specialty.
We catch up on Megan’s time up north Wisconsin, one of Jen’s former make-out sessions, and why you should always walk up the hill when your boyfriend tells you to. (Spoiler: proposals happen on hills.) We get into upcoming travel plans, pooping on vacation, Groupon purchases, Mexican food cravings, and of course, JAMAICA! Come tra...
This week, we’re joined by Jesse Lyon of Lyon Mental Health—a therapist, dream interpreter, and hilarious human who somehow made talking about the subconscious feel like a party. We get into the weird and wonderful world of wedding dreams (yes, those anxious ones with missing dresses and runaway grooms), including Megan’s cake dream that—spoiler alert—wasn't really about cake at all. Jesse breaks down what our dreams are trying t...
This week on The Planner’s Passport, we’re talking timelines—specifically, how much time you really need to plan a wedding. Whether you're stretching things out over 18 months or sprinting toward an 'I do' in six weeks, there are perks and pitfalls on both sides.
Longer planning timelines might sound like a dream (hello, options), but with time comes the temptation to overthink everything. Shorter timelines force quick decisions, s...
This week on the pod, we’re joined by one of our OG listeners — Heather Cook Elliott! To say that Megan and Jen are as mutually obsessed with her as she is with us? A massive understatement.
Heather is a Milwaukee-based wedding and portrait photographer whose work is rooted in real connection, thoughtful storytelling, and capturing people as they truly are. She’s the kind of person who shows up fully behind the camera and in lif...
This week, we’re joined by the wildly talented and hilariously cheeky Rachal A. Duggan, the creative genius behind Rad Illustrates. Known for her signature butt drawings (yes, you read that right), Rachal is an illustrator, author, and workshop leader who brings her one-of-a-kind style to everything from comics to custom wedding art.
We dive into how Rachal started drawing butts, what it’s like being a creative vendor on a wedding ...
Last week, Jen popped off about moms (and no, Megan still does not agree with her).
This week? Megan’s the one telling it like it is. And honestly? We're. Here. For. It.
She’s in her villain era, y’all. We’re talking wedding industry awards and how (surprise!) a lot of them are paid for. Not saying the people winning don’t deserve the spotlight, but it’s worth knowing there’s usually money behind that shiny badge. Transparency matt...
To be clear, Megan does not sign off on any of this. This is 100% Jen’s story arc... from superhero to supervillain wedding planner.
Now, Jen actually loves most moms. But in her experience, a few bad apples spoiled the bunch so much that she no longer works with parents unless they’ve been fully vetted.
But this episode isn’t just about mom drama (although yes, a few wild stories are share...
We’re fangirling a little harder than usual this week, because our guest isn’t just TikTok-famous—he’s also one of Jen’s former grooms… twice. (Ah, the joys of COVID-era weddings.)
Marco Braun—aka @marcosfunhouse—joins us to share the story of his two celebrations, what it was like planning during a pandemic, and how he accidentally became the internet’s vintage recipe king. Oh, and did we mention that Hilary Duff bought him and hi...
🎙️ This Week on the Podcast: We're Going Tropical, Baby! 🌴
Pack your sunscreen and questionable swimwear—we're taking this podcast to The Bahamas and want YOU to come with us! In this episode, we spill the (piña colada-flavored) tea on our upcoming getaway to Sandals Royal Bahamian. Think snorkeling with sea turtles (or at least aggressively friendly fish), late-night karaoke that may cause permanent secondhand embarrassment, and...
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