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

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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

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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

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In this episode of Now That I’m Engaged, How Do I Get Married?, Kevin sits down with Phoenix-based wedding photographer and videographer Craig Peterman, who has captured more than 500 weddings and brings a clear, practical perspective to the vendor booking process.

Craig walks couples through what really matters between the first inquiry and the moment you officially book a vendor. He explains what information to include in that first email, how to avoid overwhelming your vendors, and why communication early on sets the tone for your entire experience. He also introduces his simple Vendor Scorecard, a tool designed to help couples compare options fairly and choose their finalists with confidence.

Whether you're unsure how to reach out to vendors or feeling stuck sorting through too many choices, Craig offers a calm, actionable framework that simplifies the journey from inquiry to contract.

Highlights

• First impressions matter: How your initial inquiry sets the foundation for your vendor relationship.
• Keep it simple: The essential details couples should always include in that first message.
• The Vendor Scorecard: A quick way to narrow down your top choices and avoid decision fatigue.
• Choose wisely: Why three finalists is the sweet spot for vendor selection.
• Don’t wait too long: How a one-month research window helps you avoid losing your preferred vendors.
• Trust your instincts: What red flags to look for—and why vibe matters.
• Set a deadline: Creating a decision timeline that keeps planning on track.
• Budget awareness: Understanding your range before inquiring saves time and frustration.
• Better conversations: Tips for productive Zoom consults and clear communication.
• Enjoy the process: Why working with vendors you genuinely like leads to a better wedding day.

Craig’s thoughtful, easy-to-apply advice gives couples the tools to move from inquiry to “we’re booked!” with confidence, clarity, and far less stress.

Download the Vendor Scorecard PDFs here!

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In this episode of Now That I’m Engaged, How Do I Get Married?, Kevin and August sit down with Cherri Maley, General Manager of Messina Inn in Texas Hill Country. As a Certified Meeting and Event Planner and Certified Wedding Coordinator, Cherri brings a rare combination of logistical expertise, hospitality leadership, and heartfelt dedication to every celebration. Beyond running one of Wimberley’s most loved wedding destinations, she also serves as Chair of the Lodging & Event Section for the Wimberley Valley Chamber of Commerce—leading the region’s annual Venue Crawl, the largest wedding venue showcase of its kind in Texas.

Drawing on years of experience guiding couples through the all-inclusive planning process, Cherri breaks down what these packages actually include, why they’re so appealing to today’s engaged couples, and how to personalize them so your day still feels uniquely you. She shares how to spot hidden costs in contracts, work effectively with a venue’s preferred vendor team, and understand seasonal considerations—especially in Texas, where weather can determine everything from availability to ceremony timing.

Whether you’re overwhelmed by vendor research, trying to compare packages “apples to apples,” or simply craving a stress-free planning experience, Cherri offers practical, clear-eyed guidance that helps couples prioritize what truly matters.

Highlights

• Convenience meets clarity: Why couples love the simplicity of having lodging, catering, décor, and vendor coordination bundled in one place.
• Who it’s right for: Understanding the ideal client for an all-inclusive venue—especially couples craving ease, structure, and less decision fatigue.
• Customization matters: How to personalize packages with meaningful details, even when many services are included.
• Knowing what you’re signing: Contract tips to avoid hidden fees, unexpected upgrades, or mismatched expectations.
• Texas timing: How seasonal weather patterns affect dates, availability, and what’s realistically possible outdoors.
• Vendor harmony: Why a cohesive, venue-curated vendor team can make or break the guest experience.
• Budget confidence: How all-inclusive packages simplify financial planning and help couples stay within budget.
• Misconceptions debunked: What couples often get wrong about all-inclusive venues—and how to compare packages fairly.

No matter where you are in your planning journey, Cherri’s blend of professional insight and genuine hospitality will help you understand the true value of all-inclusive wedding packages. Her advice empowers couples to make confident decisions, avoid stress, and design a celebration that reflects their priorities—without getting lost in the details.

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In this episode of Now That I’m Engaged, How Do I Get Married?, Kevin and August sit down with Jenny MacFarlane, owner of Eloping is Fun in New York City. With 15 years of experience crafting elopements and micro-weddings, Jenny has helped over a thousand couples throw out the rulebook and design days that feel authentically them—from private vows and first-look moments to donut-shop ceremonies and Dance Dance Revolution detours.

Drawing on real client stories and NYC know-how, Jenny breaks down why “breaking tradition” isn’t anti-tradition—it’s pro-you. She shares how to reframe pressure, communicate with loved ones, and swap performative “shoulds” for meaningful choices. You’ll learn simple ways to personalize your ceremony, what to do when the guest list feels complicated, and why some couples elope now and party later for a calmer, more joyful experience.

Highlights:

• Start with how you want the day to feel, then let that guide every choice.
• “Tradition” vs. meaning: keep what resonates, toss what doesn’t.
• Guest-list freedom: micro-weddings and elopements can preserve intimacy without losing celebration.
• Eloping now, party later: reducing perfection pressure by separating the marriage from the reception.
• Real-world inspiration: a shelter-dog walk in wedding attire, a DDR arcade morning, and a cozy donut-shop ceremony.
• NYC backdrops with personality: DUMBO’s bridges, the New York Public Library, Grand Central, and Coney Island.
• Stress you won’t miss: RSVP drama, seating charts, and expectation overload.

No matter what kind of celebration you’re planning, Jenny’s presence-first, permission-forward approach will help you design a day that’s 100% you—so you can skip the pressure, savor the moments, and start married life on your terms.

Madison Humphrey Venue Video

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In this special “Taylor-era” episode of Now That I’m Engaged, How Do I Get Married?, Kevin sits down with co-host August Yocher, Susan Stremlau, Owner and Creative Director of Marion Moss Floral Design & Farm, and Ariana Teachey, Founder of Ariana Teachey | Virtual Assistant, to talk all things Taylor Swift and Travis Kelce.

From engagement-day reactions to predictions about the date, aesthetic, and overall vibe of the wedding, this Swiftie roundtable dives deep into what could become the most talked-about event of the decade and how it will influence real-world wedding trends.

Susan brings over four decades of floral design experience and a love for lush, romantic, nature-inspired arrangements, while Ariana offers a behind-the-scenes perspective on wedding pros, organization, and creative storytelling. Together, they join Kevin and August to explore everything from potential guest experiences and hidden Easter eggs to the cultural impact of this “royal couple” moment.

• Where they were when the engagement news broke
• The date debate: fall timeline vs. football season reality
• Numerology, symbolism, and Swift’s signature attention to meaning
• Aesthetic predictions: timeless vintage, secret garden romance, and Renaissance flair
• Why this engagement is huge for the wedding industry and how it may shift trends for years
• The balance of fame and privacy: intimate vows vs. all-star celebration
• How Taylor and Travis model modern partnership and mutual respect
• Favorite songs from the new album (and what they reveal about her creative mindset)

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In this episode of Now That I’m Engaged, How Do I Get Married?, Kevin and August put AI to the test in a head-to-head format: they tackle common wedding planning questions, then ask ChatGPT the exact same prompts to compare answers. They explore that while AI can be a helpful starting point, real-world expertise, context, and taste make all the difference.

From splurge-vs-save decisions to handling surprise costs, and from first-look logistics to adults-only etiquette, this episode highlights the nuances that pros bring, such as reading a venue, protecting guest experience, and balancing emotions.

Highlights:

• Start with non-negotiables: let your top 2–3 priorities drive splurge vs. save
• Build a 10–15% budget buffer for common surprises (fees, overtime, delivery/setup, permits, alterations, gratuities)
• Reallocate smartly: trim “nice-to-haves” to cover essentials without overspending
• First look vs. aisle reveal: choose based on light, venue logistics, timeline, and the feeling you want
• Adults-only wording: clear, kind, and consistent language on invites + website, with precise envelope addressing
• Planner advantage: guidance on trade-offs, timing, and budget pivots as plans evolve

No matter where you are in planning, this conversation shows how AI can spark ideas, but experienced pros help you personalize, prioritize, and protect your vision so your day feels exactly like you.

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