Expectations vs. Reality: A Retrospective on My Wedding

I’ve now spent two months trying to think of a nonchalant way to say this and I really can’t, so… I just got married!!!!!!!!! On September 7th, my now-husband Gabriel and I had our wedding at Sunset Beach Hotel on Shelter Island, and shortly before that, Man Repeller asked if I would be interested in recording my experience—specifically my expectations pre-wedding and my feelings after—to see what it revealed.

Already a frequent journaler (I love the clarity that comes from looking back on old writing to measure how much I’ve changed), I was grateful for the prompt, particularly because in the months leading up to the wedding it felt as if my brain was expanding to ten times its size in order to keep constant tabs on pressing issues like tablecloth measurements and confetti deliveries. I knew I would struggle to remember what I was actually feeling during this whirlwind of planning if I didn’t write it down somewhere. What follows are my before-and-after takes on said whirlwind, broken down by relevant category. I hope it provides a mixture of comfort, entertainment, and useful information to anyone else who might be in the midst of planning.

First Things First: My Dress and Shoes

My dress, steamed and ready to go! The sparkly veil was a last-minute addition from Kleinfeld Bridal, and I’m so glad I ended up wearing it. I love the back of the dress–you can see the daisies and ribbon we added here.


Before the wedding: I’ve already purchased my dress–it’s by Cecilie Bahnsen. I wrote about it a bit on here before, but I had a relatively easy wedding dress shopping experience. I went to Dover Street Market with both my parents (in my mind, they both have impeccable taste), tried on two Cecilie dresses and ordered the one I liked in white on Moda Operandi the next day. I’m making a few minor tweaks to it with a tailor this week. My tailor works for the Metropolitan Opera, so she really knows what it takes to make a dress look good all night. She reworked the sleeves and back so they stay in place no matter how I move, and she added little daisies (my favorite flower) to the back, plus some velvet ribbons.

My shoes I’ll be wearing are a fresh pair of the same shoes I wear every day: white patent leather Repetto Mary Janes with a 3cm heel. I’ve been wearing some version of little Mary Janes since my early teenhood, and I’ve been on a kick with these Repettos for several years now. In my opinion, they’re the perfect shoe. They have a slight 60s vibe, like my dress. They’re also comfortable. I don’t typically wear heels, and I wanted to be positive that I could dance all night. These seemed like the obvious choice, considering they’ve passed that test many times.

A Polaroid of me right after I put on my dramatic flower crown.

After the wedding: About halfway through the reception, I realized that the entirety of my look was ruined–my husband had accidentally thrown a glass of red wine across the front of my dress, a button had popped off my shoes, my flower crown was drooping, and the family heirloom cameo I wore on a ribbon around my wrist snapped and flew down the stairs into the bar where, thankfully, I was able to find it. I didn’t care. I was so happy to be married that everything else felt inconsequential, and I felt exactly like myself the entire day.

I’ve had the dress cleaned and the shoes repaired. I’ve been wearing my shoes all around town (like I said, they’re my everyday favorites), and the pearl earrings and hair clip I wore have been affixed to me almost constantly since the wedding. Now I’m just plotting when it would be appropriate to wear the dress again. The thought of buying this gorgeous dress just to give it only one day out in the world is so sad to me, which is why I purchased it with the intention of wearing it over and over. (In fact, through the early twentieth century, it was common for a bride to simply wear the best dress already in her closet to her wedding or to repurpose a wedding dress into everyday wear). Gabriel and I privately vowed that we would wear our wedding outfits every year on our anniversary, but mine may make a comeback before then….

The Food and Cake

Local oysters at cocktail hour.

Before the wedding: Sunset Beach is catering the wedding. All the food will be served family style, hopefully fostering an intimate dinner-party feeling. They have the best french fries in the world, and I’ve requested tons of them.

Our cake is by Ladurée. It’s a Marie Antoinette cake with low pale-pink tiers and lots of scalloped edges–basically a cake version of me. The flavor is Ispahan, which is my and Gabriel’s favorite dessert. It’s a French pastry composed of rose macaron, lychee cream, and raspberries. I imagine the flavor will be a bit divisive (some of my younger guests have expressed frustration that there will not be chocolate), but it’s our wedding day!

We are also having a late-night snack bar catered by The Super Snack Store. I found them through Man Repeller, naturally, and I think they are going to be a big hit.

After the wedding: Lots of people warned me I wouldn’t have time to eat dinner at my wedding, but I thought I would at least be able to sneak in at least a handful of french fries. Nope. To be perfectly honest, though, I was running on so much adrenaline I don’t think I would have been able to stomach a proper meal. That aside, it made me so happy to see everyone cozied up in candlelight, talking over beautiful plates of steamed artichoke and mussels. Guests all reported that the food was delicious. I trust their word.

Our cutie pie of a cake.

I did manage to get a slice of our cake, which I am so glad about. It was delicious. Our photographer said it was the best wedding cake she had ever tasted, which seems like a weird flex out of context, but if you’ve ever planned a wedding I know you’ll let me bask in my pride on this one…

When we finally shut off the music sometime in the early morning, Sunset Beach’s chef surprised everyone left standing with a tray of cheese fries and mini hamburgers. It was probably the best thing I’ve ever eaten.

My Hair and Makeup

My sister and I doing our finishing touches side-by-side. Clearly she hadn’t yet brushed out the Shirley Temple curls in the back of my hair!

Before the wedding: My sister, who is my Maid of Honor, is doing my hair and makeup. She’s the only person I’d trust with my appearance on my wedding day. I am really not a big hair-and-makeup person. The one time I had my makeup done professionally for an event (Prom night, 2013), I cried when I saw myself in the mirror, thereby sullying much of the makeup artist’s hard work. In general I’m fairly comfortable in front of a camera, so I’m not too worried about my appearance in photos. I’m more concerned with looking *glowy* and natural in person.

I don’t want to paint a picture of myself as being unrealistically chill, though. I’ve been obsessed with getting my skin perfect (I am a notorious picker), so I’ve been doing laser treatments once a month since February. I’ve also gotten my roots touched up twice in the past three weeks, which is truly wild for me, as I usually like to go a few months between treatments! I suppose my main beauty wish is to not have a stress pimple and to have my eyelid stop twitching (also stress), but both of these things are tenuous as of now. Will report back.

After the wedding: My sister really outdid herself. I felt beautiful and very *glowy*. My curls lasted all through the night and even into brunch the next day. I’m pretty sure I had a pimple somewhere, but we covered it, and at this point I honestly can’t even discern where it was. My eye also stopped twitching! But I spent the whole day crying, so I’m not sure how much that mattered in the end…

My best friend Julia lacing up my dress. My earrings are by Sophie Bille Brahe.

Getting ready was one of the loveliest parts of the day. My sister and I listened to 90s hip hop and drank green tea, and friends flitted in and out to give hugs and report on the shenanigans happening in the groom’s suite. In the last hour or so before the ceremony, my ten “ladies-in-waiting” (a group of little loved ones ages four to 16) all filed in and we all helped each other affix flower crowns. As crazy as it may sound, they kept me calm as we waited for our time to walk down the aisle. We sat on the floor and talked about crushes and did a last-minute dance to ‘Fergalicious’ to get our jitters out. I know that they will always be my sisters and cousins, but it did feel a little like a celebration of the last time I would really get to be a kid with them.

Here I am with all of my ladies ready to go down the aisle. They chose their own dresses, which are mostly a mix of Bonpoint and LoveShackFancy with ballet shoes–except for Charlotte, our ring bearer, who wore a suit and Air Force 1s.

The Ceremony

Before the wedding: Gabriel and I come from very different religious backgrounds, and navigating the ceremony has undoubtedly been the most difficult part of planning our wedding. The two of us have always been on the same page about what this commitment means to us, and we began our conversations about what married life would look like for us long before we were ever engaged. The challenging aspect was turning this private conversation into a very public one–not only committing to one another, but also uniting two families.

Julia leading the hand-binding portion of the ceremony while my grandfather takes a break from his officiant duties. My sister and Gabriel’s brothers stood at the altar with us.

That being said, I’m so excited for our ceremony. It’s the aspect of the wedding that I have the most trouble picturing, as it will be based on words that we are mostly keeping secret from one another until then. It’s funny how you always have this vision of who you will be by the time a big event rolls around, but when it finally arrives you feel mostly the same as always (or maybe that’s just me?). As I type this, the wedding is in nine days, and I don’t feel any more put together or eloquent or elegant than I did when we began this process back in January. If anything I feel more haphazard than usual. I think I imagined that I would feel more like an adult on my wedding day, but I’m also glad I feel mostly the same as I always do.

My grandmother and parents enjoying the ceremony–clearly one of us said something funny!

After the wedding: No one properly explained to me how wild it would be to get up in front of everyone I know and speak aloud my deepest feelings. There are parts of the ceremony that are a little hazy because I was so nervous. There was a moment of comedic relief when I couldn’t find my vows because my loveable, disorganized father had stashed them underneath my mom’s chair instead of giving them to the Best Man like I’d asked him to. Reading our vows was my favorite part of the ceremony. My vows are my favorite thing I’ve ever written, and Gabriel’s were even better. He is a spectacular poet. Our vows were honest and layered and a little bit humorous, and it felt like spreading our hearts out raw for everyone to see, in the best possible way.

My grandfather led the ceremony, and my best friend from college performed the ancient traditional Celtic hand-binding portion of the ceremony. My childhood best friend was witness to our B’rit Ahuvim, a modern Jewish equivalent to a traditional ketubah wedding contract. Immediately afterward, our parents and siblings gave heart-wrenchingly beautiful toasts in celebration. The people we love were more than just witnesses to our union, they were the ones who made it real and official. Fitting, since they are the ones who first taught us how to love.

The Music

Gabriel getting ready to sing the song he wrote for me…swoon.

Before the wedding: Gabriel is a musician, so we’ve known music would be an essential part of our wedding from the beginning. He is playing me a song he wrote at the wedding, and I can’t freaking wait to hear it. I cry any time he gets out his guitar, so I can only imagine what will happen then.

On our RSVP cards we had each guest write down a song request so that we could create a selection of music that was not wholly based upon our eclectic tastes–though we are making some very personal, very non-traditional choices for the music during the ceremony. We have a DJ lined up to mix all the song requests at the after party, but we likely won’t meet him until the wedding night! Hopefully he gets the vibe we’re going for.

Gabriel broke his ankle about a month and a half ago (while I was away for my bachelorette party, oy vey). He’ll be able to walk in time for the wedding, but we haven’t been able to practice our dance because he’s been on crutches. This is making me nervous, since neither of us are, um, super coordinated on the dance floor. My sister, who is an amazing dancer in addition to being a Youtube-worthy beauty queen, was supposed to give us dance lessons, but I guess we’re just winging it at this point.

Gettin’ down during our first dance.

After the wedding: As we hoped, our choice to walk down the aisle to Suicide’s ‘Dream Baby Dream’ really did set the tone for our wedding. People were certainly surprised, but the song is so beautiful that there were already many damp eyes when I entered with my parents (the three of us included). After Gabriel and I were officially wed, we trotted back down the aisle to ‘Doing Things that Artists Do’ by The ILYs with my ladies-in-waiting dancing after us like the little punks they truly are.

Gabriel and I shared our first dance to ‘Hellhole Ratrace’ by Girls. We both absolutely adored the band as teenagers, and it felt so poignant to be dancing to this love song again as a married couple, all those years of longing now fulfilled. We danced the same way we always do–clumsily, goofily, and joyfully–and it was just right. It’s a long song, and a couple minutes in, everyone joined in.

Gabriel designed posters as a special keepsake from our wedding. Here they are outside the dance floor for guests to take home.

The song Gabriel wrote for me was, of course, perfect and had me in tears from the moment he began. His talent will never cease to amaze me. Several of our friends played music and sang for us as well.

Our dance floor music ended up being way more 80s stuff than I expected, but that was great. One of my favorite memories of the night was dancing like crazy to New Order’s ‘Bizarre Love Triangle’ with Gabriel and my uncle. People of all ages stayed up with us well into the night, and the dance floor felt like it was in danger of caving in from all the excitement. The DJ insisted on playing ‘Sweet Caroline’ despite our instructions to avoid any corny wedding songs, but people loved it. Sometimes you just can’t beat making the crowd happy. When the dancing was done, we raced down to the beach with friends to swim in the sea.

The Decor

I had dreamt up a heart-shaped archway, and our friend James lovingly welded this one for us himself (!) out of nautical chain. The Fleurotica team filled it in with pink and yellow roses.

Before the wedding: We’ve adhered to a very specific vision of 1960s-meets-Marie Antoinette and have matched nearly everything to our specific wedding-color Pantone chips of pink and yellow. Gabriel works professionally as a graphic designer, so every aspect of our paper goods and favors have been meticulously designed. I’m mostly just feeling excited to see everything put together in the space, and I’m hoping that I get a quiet moment to admiringly soak in the decor before guests flood in.

Our flowers are by Robin a.k.a. Fleurotica, an extremely talented florist and such a sweet, calm presence—exactly the kind of energy I know I am going to need on my wedding day. We came in with a lot of super specific requests (Froot Loop-colored explosions of fruit and flowers in the style of Dutch Renaissance still lifes, 60s-style daisies sprouting from the ice in the raw bar), and she got what we were going for immediately and topped it with more fabulous ideas. I trust her so much that I am really letting her have free rein with the flowers.

Left: Luscious still life-style groups of flowers and fruit, plus our summery table linens from Heather Taylor Home. Right: Fleurotica’s gorgeous work mingling with menus and our wedding-themed Ladurée macaron boxes.

After the wedding: Fleurotica’s flowers somehow managed to transform the space that I had seen hundreds of times into something that felt completely new. Her flower crowns were these fantastical sculptures that lent the whole ceremony a dreamlike quality. The bouquet, which I initially cared the least about, ended up being an awesome addition to my look with its long neon ribbon. Lots of friends told us that the affair felt like A Midsummer Night’s Dream, which surprisingly was not on our moodboard at all, even though we both love the play! It also seemed like a real missed opportunity for a pun, given that my husband’s last name is Sommer.

The Vibe

Before the wedding: Gabriel and I love hosting dinner parties, so I think we’ve spent a lot more time thinking about the dinner section of our event than the average couple. We want the tables as large as possible to accommodate socializing, and we spent the majority of our floral budget on creating centerpieces, which is apparently unconventional. We aren’t even opening the dance floor until 10:30 pm, because we want people to be able to focus on dinner and then focus on really dancing.

Dinner tables on the upper deck just before sunset.

Finally, I hope the night stays beautifully energized and runs late! Gabriel and I have been working really hard to plan this whole shebang (read: staying up well past midnight every night running through spreadsheets and ironing patches of our crest onto 50 hand-tie-dyed sweatshirts), so the best reward will be to get to dance all night with our loved ones.

After the wedding: I expected a gathering of all our close friends and family from around the world to feel surreal, but I was not prepared for how intense it would feel to have all of them pouring out their love for us. I am still struggling to write about it. I think it’s a human experience that can only be lived (as opposed to described), a rare moment where you can feel the invisible, ever-binding netting of love that brings us together.

The wedding also became such a community effort. The night of the welcome dinner, the remnants of Hurricane Dorian blew over the island, and all of Gabriel’s groomsmen, fresh off the ferry, piled into a truck with my dad to go secure a rain tent over the dinner tables set up on the beach. The next day the sun miraculously came out, but friends and family continued to chip in, doing favors both big (securing our heart-shaped archway in the grass) and tiny (fetching me a BLT from the deli while I had my hair done).

Toasts and tears of joy during cocktail hour.

On a surface level, not all that much has changed since the wedding. Gabriel and I still live in the same tiny studio, we tend to and love each other’s families in the same way we did before, and we are still unsure about what our life together will look like in the coming years. But internally, I feel different after sharing this hugely emotional day. We lifted our love higher by revealing its depths to everyone close to us.

In the hours and days following the wedding, so many people came to Gabriel and me to tell us that we had changed their views on marriage. This was by no means something we expected to do, but it meant so much to us both. No matter how much the very concept of marriage has changed over the past few decades, I think there’s still this very prevalent idea that you have to follow a prescribed pathway or be at a certain stable point in your life in order to get married. Gabriel and I did away with every part of a traditional wedding ceremony that didn’t feel essential to us. When the whole thing came together it was a perfect picture of who we are as a couple: colorful, humorous, and deeply sentimental. It’s often quoted at weddings that love accepts you just as you are, but the wedding itself should also celebrate you as you are. If we encouraged our guests to carry that sentiment moving forward, what more could we ask for?

Photos by Jillian Mitchell.

Ruby Redstone

Ruby Redstone

Ruby Redstone is a writer, stylist, and art historian (no, seriously) from New York City.

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