Engagement Season: A Love Story in the Making
The magic of the holidays is officially underway — the twinkle of the lights, cozy dinners, and the joyful bustle of family gatherings. As the gratitude of Thanksgiving turns into the buzz of Christmas, the wedding world begins to buzz with excitement for the hundreds of thousands of couples who will say “yes” between now and Valentine’s Day.
As a planner, this is one of my favorite times of year because I get to watch so many of you go from dating to engaged, and oh, does my heart smile. This is what many like to consider, the Super Bowl of the wedding year. But before you dive into color palettes, venues, and budgets, I want to remind you that this season deserves to be savored.
Before you start scrolling through Pinterest boards or calling venues, take a deep breath and simply be engaged. This is such a sweet, fleeting season — one that deserves its own kind of celebration. Don’t rush through it trying to plan the next thing; instead, pause to take in what just happened.
Go out to dinner with your fiancé and talk about how it all unfolded. Write down the proposal story while the details are still fresh — the words, the laughter, the nerves, the moment you said yes. Call your family and best friends before you post on social media, and give yourselves permission to just exist in the joy of it all.
As a planner, I’ve seen how couples who take time to soak in the moment start their wedding journey from a place of gratitude instead of pressure. That posture, the one that says “we’re just so thankful to have found each other” will carry you beautifully through the months ahead.
Announce with Intention
Once you’ve sat and savored the moment, it’s time to celebrate with your loved ones, share the news with those near and dear, and start thinking about your engagement photos. In this era where Beyoncé’s internet is always buzzing with announcements, my favorite ones are still the simplest — the ones centered on just the two of you.
Focus on the quiet moments that led you here: the laughter, the late-night talks, the realization that within the chaos of the universe, you found your person. Whether it was through the whirlwind of online dating or the calm of your Sunday running group, that story — your story — is what makes the announcement truly unforgettable.
Jimmy + Sarah. Photo taken by The Winning Lens
While planning Jimmy and Sarah’s proposal last summer, he shared that he knew he was going to marry her within just a few months of dating. As we sat around the dinner table hours after he proposed, he told their story while Sarah looked on with a twinkle in her eyes, laughing softly at each pause. Then as his story neared the end, he grew quiet and said, “I would have found her in every lifetime.” My heart melted and from the smile on Sarah’s face, hers did as well.
That is the feeling you should carry with you as you prepare to start wedding planning — a deep knowing that love, in all its simplicity, is what this journey is truly about.
Get Organized, Not Overwhelmed
At the start of planning, I promise it’s okay not to have all the answers. For many couples, this is the first large event you’ll plan together, and naturally, there will be plenty of unknowns. So before you start researching venues and vendors, take a quiet moment to ask yourselves these three questions:
What do we want this day to feel like?
What values or traditions do we want to honor?
When we lay down the night after our wedding, what do we hope everyone remembers?
Write your answers down. Lead with the things you both value most, because that’s what will make everything else fall into place. I’ve worked with couples planning weddings with budgets anywhere from $15,000 to $150,000+ and no matter the number, the framework remains the same:
Plan for the love you share, not for the applause of social media.
When couples begin with intention, everything that follows, from budget to design, naturally aligns with who they are.
Building Your Vendor Village
Your vendor village is the second most important decision you’ll make during your engagement season. This group of people will help curate your love story. And like building a house, it takes laying each brick with care to go from engaged to unveiled at the altar.
The best vendors, in my opinion, are the ones who bring your love story to life, the ones who understand your vision, your values, and your heart for the day.
At Dasola and Bradley’s Fall 2025 wedding, Dasola wanted to ensure her mother — who was watching from heaven — was honored and celebrated. During the ceremony, her memory was beautifully represented with a framed photo placed on the first seat of the front row, where Dasola could see her while sharing her vows.
During portraits after their first look, I watched Audrey of RoseTrail Photography pause and gently suggest taking a photo of Dasola with her mother’s picture. I’ll admit, I shed a few tears. And as the ceremony began, every guest who passed that seat stopped to pay their respects a silent moment of shared love and remembrance.
That single gesture captured the heart of the day. Audrey’s attentiveness is what matters when choosing your vendors the ability to see beyond the checklist and into the emotion of the moment. It’s why those initial consultations are so important. Your vendor village’s collective effort is to tell your story authentically from the first look to the final send-off.
As you step into this new chapter of engagement, my hope is that you remember this: wedding planning isn’t just about the event, it’s about the meaning behind every decision. Announce your love with intention, get organized without losing sight of what matters, and build your village with people who see the world through your love story’s lens.
This season will move quickly the to-do lists will grow, and the details will sometimes blur, but take time to breathe in the joy of it all. You’re planning a day that celebrates not just a moment, but a promise. And that, above all else, is something worth savoring.
Dasola + Her dad with a picture of her mom on her wedding day. Photo taken by Rose Trail Images
