Why does mailing wedding invitations feel so stressful, and how can couples avoid common mistakes?

In this episode of Now That I’m Engaged, How Do I Get Married?, Kevin and August sit down with Jaime Coast, watercolor artist and stationery designer behind Cotton & Bow, to demystify the wedding invitation mailing process.

Jaime explains why couples often feel overwhelmed by invitation timelines, postage, and delivery concerns, and why the traditional six-to-eight-week rule no longer applies. She shares updated guidance on when to send invitations, especially for destination weddings, and highlights common mistakes that can lead to delays or added costs—like wax seals on outer envelopes, underestimated weight, and counterfeit stamps.

Jaime has been designing stationery since 2017 for couples looking to illustrate their love stories. She lives in Westchester, NY, with her husband and two girls. Cotton & Bow ships worldwide, with couples having a local or destination wedding.

Highlights

1. Why mailing invitations feels intimidating and how to simplify it
2. The updated timeline for sending wedding invitations
3. Common mailing mistakes that can cause delays or added costs
4. How invitation weight, size, and embellishments affect postage
5. Best practices for addressing envelopes and avoiding delivery issues
6. When tracking invitations makes sense
7. Tips for mailing international invitations safely
8. How to spot and avoid counterfeit stamps

Connect with Jaime:

Jaime’s Mailing Guide

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Vintage Stamp Dealers:

Enfield Post

Champion Stamp

Little Postage House

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What should you actually book first after you get engaged?

In this episode of Now That I’m Engaged, How Do I Get Married?, Kevin and August sit down with New York–based luxury wedding planner Sara Landon, known for designing highly curated, deeply personal celebrations with clarity and calm leadership.

Sara walks couples through one of the most important early planning concepts: the Big Three vendors—venue, photo/video, and entertainment. She explains why prioritizing these vendors early can dramatically reduce stress later, how waiting too long can limit options, and why these decisions shape the entire wedding experience. Drawing from years of hands-on planning, Sara also shares common mistakes couples make, how budgeting impacts decision-making, and why personality fit with your vendors matters just as much as talent.

Whether you’re newly engaged or feeling stuck in decision fatigue, this episode offers practical guidance to help you set priorities, avoid analysis paralysis, and move forward with confidence during engagement season.

Highlights

1. What the Big Three vendors are and why they should be booked first
2. How early booking helps reduce stress and protects availability
3. A budgeting rule of thumb to guide early decisions
4. Why vendor personality and communication matter
5. How to avoid analysis paralysis during engagement season
6. When flexibility becomes necessary, if you wait too long to book

Connect with Sara:

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Connect with Kevin & August:

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In this episode of Now That I’m Engaged, How Do I Get Married?, Kevin and August wrap up 2025 by reflecting on a year of growth, standout conversations, and the wedding planning insights couples found most helpful.

They look back on their most-played episodes, discuss recurring themes like guest experience and wedding-morning timelines, and highlight why thoughtful planning—and the right team of wedding professionals—can make all the difference. The conversation also touches on non-traditional ideas, using AI as a planning tool (not a replacement for wedding pros), weather considerations for outdoor weddings, and how pop-culture moments can influence wedding trends.

As they head into 2026, Kevin and August share what’s next for the podcast and their goal to build even more community and listener engagement in the year ahead.

Highlights

1. 27 episodes in 2025, up from 17 the year before
2. Fan-favorite episodes and guest takeaways
3. Why guest experience matters throughout the day
4. The importance of planning your wedding morning
5. Non-traditional ideas couples are embracing
6. AI as a helpful starting point—not a substitute for pros
7. Weather planning and outdoor wedding considerations
8. Looking ahead to more episodes and community in 2026

Connect with Kevin and August:

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