Alyson Thompson

Let Me Ask You This: Wedding Planning for the Logic and the Love

Society EN ↓ 32 episodes

Planning a wedding is emotional work. Nobody really tells you that — but I will. I'm Alyson Thompson, Chicago wedding planner and host of Let Me Ask You This. The logistics are real, the decisions are endless, and the emotions that show up alongside all of it? Nobody prepares you for those either. This isn't a tips podcast. It's a thinking space. So let me ask you this — what would it feel like to plan your wedding and actually enjoy it?

Author

Alyson Thompson

Category

Society

Podcast website

www.birdcageandblushers.com

Latest episode

Jul 7, 2026

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Episodes

Wedding Design: It's Not Just About How Your Wedding Looks 07.07.2026

Most couples come into the design process with a visual in mind. A color palette. A Pinterest board. An aesthetic they've been collecting images for. And that's a great starting point — but it's only the surface. The most intentional, most memorable weddings aren't designed around what something looks like. They're designed around how something feels. In this episode we're going deeper than the ae...

What Wedding Planning Reveals About Your Relationships 30.06.2026

One of the most common conversations happening among engaged couples right now is this: wedding planning revealed something about the people in my life that I wasn't prepared for. The friend who went quiet. The family member who made it about themselves. The person you expected to show up who just... didn't. In this episode we're talking about why wedding planning is one of the most revealing expe...

The Truth About the "Weddings Are for the Guests" Mentality 23.06.2026

At some point during planning, someone is going to say it. "You have to invite so and so." "The wedding is really for your family." "Your guests traveled, you need to think about them." And they're not entirely wrong — your guests matter. But somewhere along the way that idea gets distorted into something that quietly pushes you out of the center of your own wedding. And that's where it becomes a...

The Part of Wedding Planning Nobody Warns You About 02.06.2026

You got engaged and you expected to feel excited. And you do — but somewhere in the middle of the planning process, something else showed up too. Something heavier. Something nobody really prepared you for. The decisions are endless. The opinions are loud. The emotions that surface are ones you didn't see coming. And on top of all of it, you're wondering if something is wrong with you for feeling...

What You're Actually Paying For When You Hire a Wedding Planner 27.05.2026

The investment in full service wedding planning is significant. And most couples, when they see the number, immediately ask: is it worth it? In this episode I want to reframe that question entirely — because the real question isn't whether you can afford a planner. It's what you're actually getting when you hire one. We're talking about the mental load it removes, the expertise it brings, and the...

Why Wedding Planning Decisions Feel So Hard (It's Not What You Think) 12.05.2026

You've done the research. You've compared the options. You've asked everyone in your life. And you still can't decide. Sound familiar? In this episode I want to tell you why that happens — and why more information is almost never the answer. We'll talk about the real reason decisions feel impossible, what happens when logic and emotion are pulling in opposite directions, and the three questions I...

How I Actually Think About Wedding Planning — And Why It Might Surprise You 05.05.2026

Most people think wedding planning is primarily a logistical exercise. And yes — the logistics are real. But in this episode I want to challenge that assumption and share what I've learned after 13 years of doing this work: wedding planning is, at its core, a decision making experience. And the couples who move through it most confidently are the ones who understand that from the beginning. This i...

Same Show, Clearer Voice — Here's What's Changing 02.05.2026

If you've been here before, you may have noticed things look a little different. New name, new cover, new energy. In this episode, I'm taking a few minutes to talk about what changed, what didn't, and why this evolution felt necessary. Because the show I kept wanting to make wasn't quite fitting inside the one I had. So I rebuilt it — around my voice, my perspective, and the conversations I actual...

Trailer — Let Me Ask You This 22.04.2026

Wedding planning is emotional work. The decisions are endless, the opinions are loud, and somewhere in the middle of all of it, it's easy to lose the thread of what this is actually supposed to feel like. That's exactly why this show exists. I'm Alyson Thompson — Chicago wedding planner, creative director, and the person who's going to challenge you to think about this process a little differently...

The Biggest Mistake Couples Make When They Start Wedding Planning 03.02.2026

If you’re newly engaged, the pressure to start immediately is real — venues, Pinterest boards, vendor outreach, all at once. But the biggest mistake couples make in the first 30 days isn’t choosing the wrong vendor. It’s planning for aesthetics before their priorities are clear. In this episode of Handled , Alyson breaks down why rushing into decisions often leads to overwhelm, misaligned spending...

What I’m Grateful for as a Wedding Planner (And Why It Matters) 30.12.2025

This final episode of the year is a reflective one. In this episode of Handled , Alyson shares what she’s most grateful for after a full season of wedding planning — not as a highlight reel, but as a reminder of what truly matters during the planning process. From couples who trusted the process, to being invited into deeply emotional moments, to the quiet wins that never make it to Instagram, thi...

The Emotional Architecture of Wedding Planning 18.12.2025

Wedding planning isn’t just about logistics, budgets, or aesthetics — it’s about identity, relationships, expectations, and emotion. And that’s why it can feel so overwhelming, even for the most capable, organized couples. In this episode of Handled , Alyson explores the emotional architecture of a wedding — the invisible layers that make planning feel so big, so personal, and sometimes so heavy....

How to Tell If a Venue Fits Your Budget, Design, and Priorities 09.12.2025

Choosing a wedding venue isn’t just about falling in love with the aesthetic — it’s about making sure the space truly fits your budget, your guest count, your design vision, and your priorities. In this episode of Handled , wedding planner and bride-to-be Alyson Thompson breaks down the real criteria couples should be using before they book a venue — beyond vibes, Pinterest photos, and curated Ins...

Wedding Budgets: What No One Says Out Loud 02.12.2025

In this episode of Handled , Alyson breaks down the part of wedding planning no one likes talking about: the budget. Not the line items, not the price tags — but the feelings , confusion, misconceptions, and comparison culture that make couples feel shamey, stressed, or totally lost when it comes to money. You'll learn why budgeting feels so emotional, the truth about DIY “savings,” where couples...

Do These Things FIRST When You Get Engaged 25.11.2025

You got engaged — now what? Before you make a Pinterest board, book a venue tour, or say yes to anything with a deposit attached… there are foundational steps every couple should take first. And most couples skip them. In this episode, I’m breaking down the exact process I walk my Birdcage & Blushers couples through the moment they get engaged: ✨ getting crystal clear on your vision ✨ unders...

What Planners Wish You Knew Before Booking Them 11.11.2025

In this episode of Handled: A Wedding Planning Podcast , Alyson shares the insider truths every couple should know before they book their planner. From understanding what a planner actually does (and doesn’t do) to knowing what makes a great planner-client relationship thrive, this conversation is equal parts eye-opening and empowering. Let’s stay connected! Instagram: ⁠⁠⁠⁠⁠⁠@birdcageandblusherswe...

Lets Talk About Timelines 04.11.2025

In this episode of Handled , Alyson is pulling back the curtain on how she builds timelines that keep couples calm, organized, and fully present on their wedding day. She talks about everything that goes into a seamless timeline — from vendor load-ins and hair and makeup schedules to photo timing, transportation, and even pre-wedding setup and rehearsals. Let’s stay connected Instagram: ⁠⁠⁠⁠⁠@bird...

The Truth About Arguing During Wedding Planning 28.10.2025

In this episode of Handled: A Wedding Planning Podcast , Alyson unpacks why tension shows up during planning (spoiler: it’s rarely about napkin colors), how to understand the emotions beneath disagreements, and ways to communicate and compromise without losing connection. Let’s stay connected Instagram: ⁠⁠⁠⁠@birdcageandblushersweddings⁠⁠⁠⁠ Work with me: ⁠⁠⁠⁠https://www.birdcageandblushers.com/cont...

The Vendor Maze: How To Choose Without Getting Overwhelmed 21.10.2025

Choosing your wedding vendors shouldn’t feel like navigating a maze of emails, contracts, and conflicting opinions. In this episode of Handled , Alyson breaks down how to find the right vendors for you —the ones who align with your values, energy, and vision, not just your budget. Let’s stay connected Instagram: ⁠⁠⁠⁠@birdcageandblushersweddings⁠⁠⁠⁠ Work with me: ⁠⁠⁠⁠https://www.birdcageandblushers...

Budget Stress Without the Shame 14.10.2025

Money and emotions are deeply connected — especially when you’re planning a wedding. In this episode of Handled: A Wedding Planning Podcast , Alyson opens up about the pressure couples feel around wedding budgets, from navigating family opinions to comparing costs online. She shares how to reframe budget stress into clarity and confidence, what to focus on when decision-making feels heavy, and why...

More Than a Moment: The Emotional Side of Wedding Photography 07.10.2025

Wedding photos are more than beautiful portraits—they’re emotional time capsules. In this episode of Handled: A Wedding Planning Podcast , Alyson sits down with Chicago-based photographer Winterlyn Stebner of Winterlyn Photography to explore the feelings behind wedding photography and what it means to be truly seen on your wedding day. Together, they talk about vulnerability in front of the camera...

Wedding Party Roles: Who Actually Does What (and What They Don’t) 30.09.2025

In this episode of Handled, Alyson Thompson discusses the essential roles and responsibilities of wedding party members, emphasizing the importance of clear communication and setting expectations. She contrasts traditional wedding party roles with modern practices, highlighting the need for support rather than production. The episode concludes with key takeaways for couples to ensure a smooth wedd...

Decision Fatigue: How to Handle Many Choices You’ll Make 23.09.2025

In this episode of Handled, Alyson Thompson discusses the phenomenon of decision fatigue, particularly in the context of wedding planning. She explains how overwhelming choices can lead to stress and frustration, and offers practical strategies to manage this fatigue. ✨ Let’s stay connected Instagram: ⁠⁠⁠@birdcageandblushersweddings⁠⁠⁠ Work with me: ⁠⁠⁠https://www.birdcageandblushers.com/contact-...

What a GOOD Wedding Planner Actually Does 16.09.2025

In this episode of Handled, Alyson Thompson discusses the true value of hiring a wedding planner, debunking common misconceptions and highlighting the emotional and logistical benefits that come with professional support. She emphasizes that a good planner not only manages logistics but also provides emotional support, helping couples navigate the complexities of wedding planning with confidence a...

Venue Contracts Decoded: What You're Really Signing Up For 09.09.2025

In this episode of Handled, Alyson Thompson delves into the intricacies of venue contracts, emphasizing their importance in the wedding planning process. She discusses key elements to look for in contracts, such as inclusions, timing, vendor restrictions, and cancellation policies. Alyson also highlights potential red flags and smart questions couples should ask to ensure they fully understand the...

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