
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... more
| Publishes | Weekly | Episodes | 38 | Founded | a year ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | RelationshipsSociety & Culture | |||

Every couple eventually has the same moment. You open a proposal, look at the price, and wonder... "Is this actually worth it?"
In this episode, we're exploring how to evaluate wedding investments beyond the numbers on a proposal. We'll talk about w... more
Wedding planning is supposed to be one of the happiest seasons of your life.
So why do some people describe it as... lonely?
In this episode, we're talking about an emotional side of wedding planning that rarely gets discussed. From unmet expectati... more
One of the biggest misconceptions about hiring a wedding planner is that you'll lose control of your wedding.
But what if the opposite is true?
In this episode, we're reframing what it really means to work with a planner and why the best planning r... more
Most couples don't choose a wedding venue.
They react to one.
In this episode of Let Me Ask You This, we're talking about why venue searching feels so overwhelming—and why one of the biggest decisions you'll make in wedding planning is often made b... more
Within days of getting engaged, most couples are already wondering if they're behind. The venue isn't booked yet. The vendors aren't locked in. And somewhere between the checklist you found online and the third person who asked if you've picked a dat... more
The wedding industry has been having a lot of conversations about pricing transparency lately.
Should vendors publish their prices? Should couples have to inquire before knowing an investment? Is sticker shock a transparency problem?
In this specia... more
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... more
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 themsel... more
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Listeners, social reach, demographics and more for this podcast.
| Listeners per Episode | Gender Skew | Location | |||
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This program focuses on wedding planning as an emotional, value-driven process rather than a set of quick tips. Across episodes, the host emphasizes slowing down, clarifying priorities, and co-creating a plan that aligns with a couple's identity, budget, and desired experience. Key themes include managing decision fatigue, reducing mental load, and designing a wedding that feels personal and authentic by treating design as an experiential architecture. The show also explores how relationships, family dynamics, and external pressures influence planning, and it often reframes problems to empower couples to plan with both logic and love. A notable strength is the host's ability to translate complex emotions and practical constraints into actio... more
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These podcasts share a similar audience with this podcast:
1. The Unconventional Wedding Planning Podcast
2. Unbridely - Modern Wedding Planning
3. Wedding Day Podcast
4. Wedding Hive Podcast
5. Dear Shandy
this podcast launched a year ago and published 38 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on this podcast include:
1. Winterlyn Stebner
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