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

Alyson Thompson
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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?

  1. Jun 2

    The Part of Wedding Planning Nobody Warns You About

    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 this way. Nothing is wrong with you. This is just the part nobody warns you about. In this episode we're talking about what actually makes wedding planning so emotionally heavy, why the weight of it catches even the most organized couples completely off guard, and how to move through it in a way that doesn't cost you the joy of the experience. This one is for the couple who is already in it — already planning, already feeling the weight of it, and wondering if it's supposed to feel like this. Connect with Alyson: 🌐 birdcageandblushers.com 📲 @birdcageandblushers

    8 min

  2. May 27

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

    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 elevated result it makes possible. This one is for anyone who has ever wondered what a planner actually does — and whether the investment makes sense for them.

    9 min
  3. Why Wedding Planning Decisions Feel So Hard (It's Not What You Think)

    May 12

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

    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 ask my own couples when they're stuck that do more work than any spreadsheet ever could. . . . Connect with Alyson: 🌐 https://www.birdcageandblushers.com/📲 @birdcageandblushersweddings

    6 min
  4. How I Actually Think About Wedding Planning — And Why It Might Surprise You

    May 5

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

    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 is my philosophy. And it changes everything. . . . Connect with Alyson: 🌐 https://www.birdcageandblushers.com/📲 @birdcageandblushersweddings

    8 min
  5. Same Show, Clearer Voice — Here's What's Changing

    May 2

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

    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 actually want to be having with you. This is still me. Just more of me. . . . Connect with Alyson: 🌐 https://www.birdcageandblushers.com/📲 @birdcageandblushersweddings

    3 min
  6. Trailer — Let Me Ask You This

    Season 2 Trailer

    Trailer — Let Me Ask You This

    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. Let Me Ask You This is a podcast for couples who want more than timelines and vendor checklists. Who want to understand the decisions they're making and feel good about how they're moving through the process. Every episode we'll explore both sides — the logical and the emotional — because you need both to plan a wedding you'll actually love. This isn't a tips podcast. It's a thinking space. New episodes dropping soon. Subscribe now so you don't miss them.

    1 min
  7. The Biggest Mistake Couples Make When They Start Wedding Planning

    Feb 3

    The Biggest Mistake Couples Make When They Start Wedding Planning

    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, and unnecessary stress — and what to do instead. You’ll learn how establishing clear priorities early becomes the framework that makes every decision after that feel easier, faster, and more confident. This episode is especially for couples who want a planning process that feels intentional, grounded, and actually enjoyable — not reactive. Let's connect! Instagram: @Birdcageandblushersweddings Website: www.birdcageandblushers.com

    13 min
  8. What I’m Grateful for as a Wedding Planner (And Why It Matters)

    12/30/2025

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

    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, this episode explores the unseen layers of wedding planning that shape how a day feels, not just how it looks. Alyson reflects on presence over perfection, connection over performance and more. As we head into a new year and a new wave of engagements, this episode is a grounding reminder that you don’t have to plan perfectly — just honestly, intentionally, and with support that makes you feel safe. Let's connect! Instagram: @Birdcageandblushersweddings Website: www.birdcageandblushers.com

    16 min
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Trailers

About

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?

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