Olivia Gibbons & Jason Howick – Historic Dubsdread, 11/23/2024
Photography: Right Up Your Allie
Flowers: Cloudless Sulphur
Music: iRock Your Party
Cake: Everything Cakes
Officiant: Father Richard Walsh, St. Margaret Mary Catholic Church
Draping: W Drapings
Wedding Planner: Dani’s Event Design
Photobooth: The Van Cam
Makeup: Makeup by Taylor Thomas
Hair: Alchemy Orlando
Some love stories begin with a spark, but for Olivia and Jason, it started with friendship over shared shifts at Wine Bar George in Disney Springs. That friendship soon blossomed into romance after their first date in November 2019, and years later, Jason surprised her with a magical sunset proposal on a trip to Jamaica. From cliff jumping by day to saying “yes” by the ocean at dusk, their journey together has been full of adventure, laughter, and heart. When it came time to plan their wedding, they envisioned a celebration that was warm, elegant, and true to who they are—and Historic Dubsdread turned out to be the perfect place to bring that vision to life.
Love Story & Proposal
How did you two meet?
We met while working together at Wine Bar George in Disney Springs. We started off as friends, and it grew into something more after Jason asked me on a date in November 2019.
Tell us about the proposal! Where did it happen and how did it go?
We went on a trip together in Jamaica at the beginning of August 2023. I would have said yes, anywhere in the world with Jason, but saying yes during sunset in Jamaica after a day of cliff jumping, swimming and being in the sun made it very magical.
Wedding Planning Journey
What was your overall vision or theme for the wedding?
We wanted something that was warm, inviting, and true to ourselves. Romantic, elegant, but not uptight.
What made you choose Historic Dubsdread as your wedding venue?
We live just down the street from Dubsdread, and it’s a place where we have spent many lunches on the porch. We had an initial vision of a more DIY approach, but that quickly became overwhelming. After our visit, we felt that Dubsdread provided the best of both worlds, and we trusted the team.
What were your top 3 priorities during the planning process?
- To always remember what we were doing this for. Not to aim for perfection, but to officially start our lives together as husband and wife. The marriage is first; the wedding was going to be fun no matter what because we have wonderful people in our lives!
- To keep the planning as fun as possible. We wanted to carve out a specific time to focus on wedding planning and not have it consume every moment. Cake tasting, menu tasting/decisions, playlist making. We tried to make those activities more into date nights, so not everything turned into a stressful budget talk
- To not get carried away and look at social media too much. There’s so much comparison, and it’s unnecessary.
Did you work with a planner or coordinate the wedding yourselves?
Yes! We are not terribly organized, so after a couple of weeks of planning it ourselves, we decided it would be worth it to hire a wedding planner/coordinator to relieve us of the stresses of planning. Dani was wonderful, level-headed, and made fantastic recommendations. So happy with our decision.
How did you stay organized and manage stress during planning?
With Dani’s Event Design. And lots of help from family and friends.
Wedding Style & Details
Describe your wedding-day look: what you wore and why you chose it.
I wore a dress by the designer Madi Lane. And I loved my mantilla-style veil. I also had some gloves that my grandmother wore for her wedding in the 1960s. I’m obsessed with them. Jason wore a black tux and looked so handsome.
How did you choose your wedding colors, florals, and décor?
We gave our florist a mood board and trusted her with it all. Just loved the rich tones!
Were there any DIY or personalized elements you included?
A couple of things! My sister is a talented artist, and she designed our Save-The-Dates. She was so generous to contribute her talents, and I loved the way they turned out.
For our card box, we used an old wooden wine box we collected while working together at the wine bar. We had a nice time collecting photos from our parents and grandparents of their weddings, too. A small detail, but very personal.
We also played a recording of Jason’s late grandmother playing piano when his parents were little. It was the interlude music for the wonderful speeches from the night—more tears, of course.
Did you have a favorite vendor or must-have detail?
We loved our DJ!! They kept the dance floor full all night long. And I cried happy tears when I saw all the florals.
Wedding Ceremony & Reception
What was the most memorable moment of the day?
Walking down the aisle with my dad and seeing Jason at the front of the church. Or some special songs, dancing and singing along with our families.
Did you do a first look? Why or why not?
Yes! It was mostly for practical reasons. We wanted to enjoy the cocktail hour and the entire wedding reception, so we took our couple portraits beforehand. It helped ease some nerves. And the walk down the aisle was still unforgettable.
What songs did you choose for your ceremony, first dance, etc.?
Our first dance song was a cover of The Promise sung by Sturgill Simpson. Then Sebastian (DJ) played the When in Rome version later in the night, like we requested. It was awesome. My dad and I danced to These are Days by 10,000 Maniacs, and Jason and his mom danced to “Nothing Else Matters” by Metallica.
How did you make the reception fun and unique for your guests?
Our guests really enjoyed the Van Cam. A photo booth with a theme and fun props. The weather was also lovely in November, so guests could find a comfortable place anywhere in the venue- whether it was older guests who wanted to catch up around a table outside or the cousins who wanted to dance all night.
Wedding Photo Tips
Do you have a favorite wedding photo? What’s the story behind it?
So many! We love our photos from the first look, and all the photos with our parents. It’s so beautiful to see the emotions captured and the expressions of pride, gratitude, and pure love from them.
Any advice for couples on working with photographers?
Trust your photographer! Definitely make a thorough list of the shots that you’d like beforehand. Be as easy and breezy as possible because it will translate on camera.
Advice & Reflection
What was your favorite part of the entire day?
When we were seated at our sweetheart table, looking around at all our guests…family and friends who came from all over to celebrate. It was an incredibly gratifying moment.
If you could relive one moment, what would it be?
Probably that one. There was nothing like it. All the love in your life in one room. Once in a lifetime.
Is there anything you would change about your wedding/wedding day?
Not really. It felt hectic in the morning, so I wish I’d done everything to make the getting-ready portion seamless, but life isn’t perfect, and it ended up being the best day ever. There’s so much you let go of as the day goes on because the only thing that matters is that you got MARRIED!
What advice would you give to other couples planning a wedding?
Take it day by day. And feel good about your decisions. It’s very easy to get decision fatigue and to feel pulled in all different ways by many different voices. At the end of the day, you are getting married to your love. It is a beautiful and sacred moment, and the most important decision.
Also, we want to share a great tidbit of advice we got from the couple who helped us prepare for marriage at St. Margaret Mary.
The week prior to your wedding, go on a date night and don’t mention the wedding at all. None of the stresses or anxieties. Just focus on each other and have a nice, simple, meaningful date night. You’ll be reminded of how far you’ve come.
