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.
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.
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 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!
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.
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 megan@daretodreamtravelwi.com #beachesnegril
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.
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.
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.
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.
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.
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
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.
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.
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.
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 matters, and Megan’s not holding back. Tune in! Why? Because it’s so fun when Megan spills the dirt.
This week’s episode is all about moms. 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 shared). It’s really meant to help moms navigate the modern wedding planning journey. A lot has changed since their own wedding days... and let’s just say, some of them struggle with that. So this one’s for you, moms. We’re here to help so that you don't become a Momzilla. Oh! We also spend a solid 15 minutes talking about “John Smith” (name changed to protect the extremely attractive but not-so-innocent boy everyone had a crush on in high school). You don’t want to miss it.
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 his husband their registered china after he went viral for being the world’s biggest Lizzie McGuire fan? We talk about love, weddings, internet fame, and yes… a very passionate discussion about mayonnaise. It’s hilarious, heartwarming, and everything you didn’t know you needed today.
🎙️ 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 tropical drinks with umbrellas that are fancier than our actual wardrobes. We're giving you the inside scoop on what it's like to party podcast-style in paradise, how to snag your spot on this sandy adventure, and why your mom, best friend, or mildly chaotic partner absolutely needs to come too. It’s happening November 30–December 3, and it’s going to be legendary… or at least mildly sunburned and extremely fun. 🌞🎤🌊 Want more info or to get your room on hold? Reach out to Megan at megan@daretodreamtravelwi.com or check out our trip page at http://www.daretodreamtravelwi.com/join-us-bahamas.html See you on the beach! Megan & Jen
This week, Jen’s in Sonoma County to facilitate a bachelorette party , but let’s be real, she also used the trip to scout the region for future travelers (because of course she did). From sipping sparkling wine at Iron Horse Vineyards to inhaling the best vegan quiche of her life at Little Saint in Healdsburg, this episode is packed with wine country magic and mild chaos. She stopped in Bodega Bay for oysters, explored Calistoga for those cute Northern California vibes, wandered around The Barlow in Sebastopol, and managed to fit in a date—because you know how Jen rolls. This one happened with a sommelier who lives in a van (Megan would like you to know it’s technically a camper). Oh, and there was vomiting in the bathroom (not Jen, chill). Tune in for travel inspo, planning tips, wine recs, and everything you should (and definitely shouldn’t) do on your next Sonoma County trip.