Most Commonly Asked Questions About Event Planning

On an episode of the Wine and Dine Me Podcast (Apple Podcast or Spotify), we flipped the script and I was in the interview seat for once. I was asked some of the most common questions we get from potential clients, and let me tell you—it was such a fun, candid conversation! If you’ve ever wondered about the ins and outs of working with Reagan Events or just need a little insight into luxury event planning, this one’s for you.

Let me dive in and share the highlights, straight from the heart.

“Reagan Events—what’s your elevator pitch?”

We started with the big one, and honestly, it’s a question I love answering. What do we do at Reagan Events? It’s simple: “We plan epic parties.” Whether it’s a wedding, a milestone birthday, or a jaw-dropping corporate celebration, we create unforgettable experiences for people who are bold, daring, adventurous, and just genuinely good humans. That’s who we are, and that’s who we do it for.

“How much does it cost?”

Ah, the million-dollar question—literally sometimes! Here’s the truth: “It depends.” I always tell clients it’s like building a house. Do you want a five-bedroom, three-bathroom home or a sprawling estate with custom finishes? Are we tenting a private estate from the ground up or working in a space that’s already event-ready? The key is transparency. We guide you through an initial scope and constantly revisit the budget as we go. Think of it as a discovery process, and yes, it’s a collaborative one.

One thing I want to stress? While we bring years of expertise to the table, we’re ultimately at the mercy of market prices. It’s a bit like a general contractor dealing with fluctuating lumber costs. We’ll always keep the dialogue open, so there are no surprises—and so you can make the best decisions for your day.

Starting Your Journey with Us

When we first start working together, we love to kick things off by simply listening to your story. “Of course we want to hear how you met,” I tell clients, “but we also want to know how you live, how you travel, how you entertain.” We send over our signature initial steps questionnaire—a fun and meaningful exercise that often doubles as a fabulous date night. It’s designed to get you thinking about what really matters to you as a couple and to give us the insight we need to make your vision a reality.

The Design Process: Turning Your Why Into Wow

One of my favorite parts of the planning process is taking all of your inspiration and digging into the why behind it. “Why was that truffle-laced egg brunch in Montalcino one of your most unforgettable moments?” or “Why is a particular tradition so meaningful to you?” It’s in the “why” that we find the soul of your event. From there, my team translates that into those wow-inspiring moments. It’s deeply personal, it’s collaborative, and it’s always magical.

Yes, We Travel Everywhere

One question we hear often: “Do you travel?” The answer is always yes. Most of our events are destination events, and we love that. Whether it’s Lake Como, Napa, or a private estate in France, our passports are ready. Don’t worry if we’ve never worked at your chosen location before—we have the experience, connections, and confidence to make magic happen anywhere. I always tell clients, “Don’t feel like you have to hire someone local just because you think we’ll struggle. We’ve done this before, and we’ll do it again.”

Not Just Weddings: Why I Love Non-Wedding Parties

Okay, I’ll admit it—some of my absolute favorite events aren’t weddings. From private dance parties with DJs that keep the energy going all night to immersive milestone celebrations, I live for creativity and epic experiences. One of my favorite projects? A 60th birthday party we planned in a chic, hidden art gallery accessed by a freight elevator in an urban warehouse district. “Where are we going?” guests whispered as the elevator doors opened into a stunning, unexpected venue. It was unforgettable.

Transparency and Teamwork: How We Operate

Transparency is at the core of everything we do. From live updates on your budget to weekly planning check-ins, we ensure you’re always in the driver’s seat. And when it comes to decisions like splurging on an incredible band, we help you find balance by scaling back in other areas if needed. It’s all about working together to create the perfect event—your way.

What We Don’t Do

There are a few things we don’t handle directly—like assembling welcome gifts or managing room blocks—but rest assured, we partner with the best people to take care of it for you. Think of us like your general contractor. If there’s a task outside our scope, we bring in the experts and oversee it all to ensure perfection.

The Reagan Events Difference

We intentionally limit the number of events we take on—just 6–8 weddings per year—so we can give each client the high-touch experience they deserve. My team and I collaborate on every single event together, and on event days, our team grows to include 5–10 assistants (or more, if needed). As I like to say, “We like our staff the way we like our bars—overstaffed.” This commitment to detail and service is what allows us to create truly extraordinary events.

If you’re recently engaged or planning a special celebration, I’d love the chance to create something epic with you. Where are we going? Greece, London, Napa, Italy—let’s dream big together.

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