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. 3 FEB

    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

  2. 30/12/2025

    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

  3. 18/12/2025

    The Emotional Architecture of Wedding Planning

    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. From identity shifts and family dynamics to money narratives, social pressure, and the gap between Pinterest and reality, this conversation validates what so many couples are feeling but rarely hear acknowledged. If you’ve ever wondered “Why does this feel so intense?” or “Why am I struggling with decisions that should feel simple?” — this episode is for you. You’ll leave feeling grounded, understood, and reminded that you’re not doing anything wrong. This is your permission to slow down, lead with values, and plan from a place of intention — not pressure. Let's connect! Instagram: @Birdcageandblushersweddings Website: www.birdcageandblushers.com Learn more about the Venue Shortlist System: https://www.birdcageandblushers.com/venue-shortlist-system

    20 min

  4. 09/12/2025

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

    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 Instagram grids. You’ll learn:• Why beautiful photos don’t tell you the whole story• The three non-negotiables every couple should identify before touring• How guest count, priorities, and budget quietly shape everything• Hidden venue costs couples rarely know to ask about• How rentals, catering models, lighting, and logistics impact your bottom line• Why the venue determines up to 70% of your total budget• How to avoid falling in love with a space that simply can’t support your vision Alyson also shares why she created her signature Venue Shortlist System — a personalized process that helps couples narrow their search to spaces that truly align with their guest count, design goals, logistics, and budget. If you’re in the early stages of planning, or if you have no idea where to begin with venue hunting, this episode is your roadmap to making confident, aligned decisions. Learn more about the Venue Shortlist System: https://www.birdcageandblushers.com/venue-shortlist-system Let's Stay Connected: Instagram: @Birdcageandblushersweddings Website: www.birdcageandblushers.com

    9 min

  5. 02/12/2025

    Wedding Budgets: What No One Says Out Loud

    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 overspend without realizing it, and how to make aligned, confident financial decisions based on your values — not panic or pressure. Alyson also shares insider tips on labor, rentals, florals, catering styles, and why “cheap” often isn’t cheaper. If you’re overwhelmed, conflicted, or wondering why this part of planning feels so hard, take a deep breath. You’re not alone — and this episode will help you handle it with clarity, confidence, and calm. Book a Planning Power Session Instagram: ⁠⁠⁠@birdcageandblushersweddings⁠⁠⁠Work with me: ⁠⁠⁠https://www.birdcageandblushers.com/contact-chicago-wedding-planner⁠⁠⁠Email: ⁠⁠⁠info@birdcageandblushers.com

    24 min

  6. 25/11/2025

    Do These Things FIRST When You Get Engaged

    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✨ understanding your budget without the shame spiral✨ learning how to approach the venue search strategically, not reactively If you want to avoid months of stress, overwhelm, and costly wrong turns, this episode is your starting point. And if the venue search already feels like too much? I created my Venue Shortlist System specifically to save you time, money, and decision fatigue — so you can start your planning with confidence and clarity. Learn more about the Venue Shortlist System: https://www.birdcageandblushers.com/venue-shortlist-system Let’s stay connected! Instagram: ⁠⁠⁠⁠⁠⁠⁠@birdcageandblushersweddings⁠⁠⁠⁠⁠⁠⁠ Work with me: ⁠⁠⁠⁠⁠⁠⁠https://www.birdcageandblushers.com/contact-chicago-wedding-planner⁠⁠⁠⁠⁠⁠

    18 min

  7. 11/11/2025

    What Planners Wish You Knew Before Booking Them

    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: ⁠⁠⁠⁠⁠⁠@birdcageandblushersweddings⁠⁠⁠⁠⁠⁠ Work with me: ⁠⁠⁠⁠⁠⁠https://www.birdcageandblushers.com/contact-chicago-wedding-planner⁠⁠⁠⁠⁠⁠ Email: ⁠⁠⁠⁠⁠⁠alyson.thompson@birdcageandblushers.com⁠

    6 min

  8. 04/11/2025

    Lets Talk About Timelines

    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: ⁠⁠⁠⁠⁠@birdcageandblushersweddings⁠⁠⁠⁠⁠ Work with me: ⁠⁠⁠⁠⁠https://www.birdcageandblushers.com/contact-chicago-wedding-planner⁠⁠⁠⁠⁠ Email: ⁠⁠⁠⁠⁠info@birdcageandblushers.com⁠

    10 min
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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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