Advertise on podcast: The Planner’s Passport - Wedding Planners, Travel Agents, Decades of Stories
Rating
5from
This podcast has
46 episodes
Language
EnglishPublisher
Megan P. & Jen G.Explicit
No
Date created
2024/11/06
Latest episode
2025/10/22
Average duration
48 min.
Release period
9 days
Description
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
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Check latest episodes from The Planner’s Passport - Wedding Planners, Travel Agents, Decades of Stories podcast
Vendor Spotlight: Grace of Tarot D'Amore
2025/10/22
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 blending tarot with love and ceremony, and the powerful ways she helps people navigate big transitions with clarity and compassion.
It’s soulful, fascinating, and full of insight. You don’t want to miss this one.
Can you tell if a couple is going to make it?
2025/10/15
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 the way, and the subtle signs that reveal how two people really work together when the pressure’s on. It’s honest, funny, and maybe a little unfiltered, but that’s what makes it good.
If you’ve ever wondered what planners really think after seeing hundreds of weddings from behind the scenes, this one’s for you.
Wedding Day Timelines 101: Why Everything Takes Longer Than You Think
2025/10/08
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 going to take 90 minutes.
We’ll talk about how to build a timeline that keeps the day moving (without rushing it), why buffer time is your new best friend, and the secret to avoiding the dreaded “we’re running late” announcement.
If you’re planning a wedding — or you just love hearing planners rant about timelines — this one’s for you.
The Wedding Industry: We're Here to Make Money
2025/09/24
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 you — but professionals in this space are running businesses that take time, skill, and energy to deliver amazing results. And that’s something worth valuing.
The reality is simple: experience and expertise matter. The longer someone has been doing this and the better they are at it, the more their services are worth. That’s true in every profession. And just because something has a higher price tag doesn’t mean it’s unfair or inflated.
Think about it this way — would you want someone walking into your workplace and telling you to cut your paycheck in half because they “feel like it”? Probably not. Weddings are no different.
Do you agree or disagree? Tune in this week to hear more!
Non-Negotiables: The Wedding Hills We'll Die On
2025/09/17
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 honest advice, expert tips, and strong opinions.
Travel to Beaches Negril: Our Perfectly Imperfect Vacation
2025/09/10
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 key when traveling, and how even a perfectly imperfect vacation can create unforgettable family memories. If you’re planning a trip to Beaches Negril or just love real stories about family travel, this episode is for you!
Interested in planning your own family vacation to Beaches Negril or Beaches Turks and Caicos? Reach out to Megan for free travel planning services or check out her YouTube Channel, The Sandals Insider to hear more!
Dare to Dream Travel
www.daretodreamtravelwi.com
[email protected]
#beachesnegril
Kids or No Kids? The Great Wedding Debate
2025/09/03
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 advice you need.
Weather or Not: The Big Day Must Go On
2025/08/27
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 to weather-proof your wedding.
Whether you’re dreaming of a summer garden party, a lakeside celebration, or a cozy winter wedding, this episode is packed with tips to help you stay prepared and keep the day running smoothly, rain or shine.
A Wedding Planner’s Guide to Hair and Makeup
2025/08/20
Let’s be real—your hair and makeup team can make or break your wedding morning vibe. In this episode, we’re chatting about why you shouldn’t wait to put down that deposit (yes, glam squads book up fast!), how to speak up during your trial so you actually love your look, and why the big day beauty is always, always about the bride (sorry Aunt Karen). We’ll share funny stories, real talk, and planner-approved tips so you can walk down the aisle feeling like the star of the show—because you are.
Tea for Two: Wedding Planners Spill All
2025/08/13
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 to poop in the bridal suite. You'll have to listen to find out who.
It’s unfiltered, a little unhinged, and 100% real. If you’ve ever thought wedding planning was all peonies and Pinterest boards... buckle up.
Catching Up with Jen and Megan: Proposals, Poop, and Travel Plans
2025/07/30
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 travel with us.
SPECIAL ALERT: If you’ve been thinking about advertising with us, now’s your moment. Get in at the basement level and grow with us because this elevator is going up.
So no, it’s not nothing. It’s everything. It's hilarious. And it’s very us. Press play.
Decoding Your Wedding Dreams with Jesse Lyon
2025/07/23
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 to tell us during high-stress seasons like wedding planning, how therapy can help us navigate the chaos, and why he thinks your mental health team deserves a seat at the vendor table.
It’s insightful, entertaining, and one of our favorite convos yet.
Lyon Mental Health
@lyonmentalhealth
Short or Long? The Engagement Showdown
2025/07/16
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, streamline the process, and reduce waffling—but they also come with logistical curveballs and fewer available vendors.
We break it all down: from decision fatigue to vendor availability, budget impact to emotional whiplash. And in true fashion, we absolutely go off the rails at least once, possibly more. You already know.
Whether you're a type-A planner or a last-minute lover, this one’s for you.
Behind the Lens with Heather Cook Elliott Photography
2025/07/09
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 life, and we absolutely adore her.
In this episode, we dive into Heather’s origin story, what it’s like building a creative business with soul, and why we all can’t stop giggling through this whole conversation. Spoiler: Heather’s coming with us to Jamaica. Are you??
Tune in for major bestie energy, industry insight, and a whole lot of love.
Live Wedding Art with a Side of Booty
2025/06/18
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 day, and the unexpected chaos of live event sketching.
From editorial and branding illustrations to teaching private drawing workshops, Rachal does it all and somehow makes it all hilarious. Tune in for puns, laughter, and an honest peek behind the (butt) curtain of wedding day artistry.
Follow her work on Instagram and TikTok @radillustrates.
Podcast reviews
Read The Planner’s Passport - Wedding Planners, Travel Agents, Decades of Stories podcast reviews
Nolagirl463 2024/11/27
November 2025 Wedding
My daughter is getting married November 2025 in Milwaukee. We(her parents)live on the East Coast and it will be very helpful to get some wedding/plan...
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