Do you remember the [second] night of September?

(Originally published on Medium on September 30, 2017)

I think I always will.

About a year ago, I had been asked by one of my closest friends to be her Maid of Honor in her wedding in San Francisco. Under the condition that one day, she would do me the same honor at my wedding, I accepted her proposal.

I was flattered and excited to be able to do this for her. At the same time, I was terrified because I had absolutely no idea what I was doing. Of all the things I did or didn’t do as Maid of Honor, the three I am proudest of are:

  1. Coordinating a 3-day “destination” Bachelorette party in Miami Beach with an appropriately full but fun schedule.
  2. Carrying a 25–30-pound dress, covered in a thick plastic garment bag, in a record-breaking San Francisco heat wave of 100+ degrees.
  3. Delivering a toast that will be hard to top if someone asks me to do give a speech at his/her wedding in the future

Number 1 can be summarized with “beach, booze, and brunch.” Number 2 speaks for itself. Number 3 deserves more detail.

Sometime after the Bachelorette party, I started thinking about the toast and free-writing down everything I wanted to say about the bride. Reviewing the notes and trying to patch them together into a speech wasn’t working out too well: the sentimental anecdote I had prepared was too sad and more about me than about her, and very little of the drafted content of the speech had anything to do with the groom aside from using his name once. On the whole, the toast felt very generic — like someone could have put it on any or all of the 5 websites I had looked at with blog posts titled “How to write a great Maid of Honor toast!”

How do you encapsulate everything you could possibly want to say about someone you love on one of the most important days of her life? On one hand, there is too much to say. On the other hand, there’s nothing to say, because you’re speechless.

About a month before the wedding, I had an idea that caused me to scrap everything that I had come up with for the toast. I decided I was going to channel my Grandmother — my awesome Grandma Toby who recites a rhyming poem she writes for every special events for friends and family — and do something lyrical.

I have the bride to thank for a lot of obsessions —Tom Ford lipstick, the latest one — but the one most relevant to the speech would be Hamilton: An American Musical. She hooked me on the soundtrack in the spring of our second year of business school and turned my initial skepticism of the show into an addiction. I had become one of those Broadway showtune people that generally drove me crazy, living near Emerson College in downtown Boston with its hordes of theater students.

I resolved that I would take a song from the show, rework the lyrics into a wedding toast. If nothing else, I figured 1. Restricting myself to the length of a song would prevent the toast from getting too long 2. Singing a toast instead of speaking it would be a little unexpected and interesting for the attendees (in a good way), provided I didn’t lose my voice or drink too much.

Then it came down to picking the song. Striking from the list the rap battles, the sadder minor key melodies, and any song that was already overused in Hamilton-inspired wedding toasts on YouTube, I decided on the ballad “Dear Theodosia.” It’s a heartfelt gem tucked in at the end of Act 1, in which Aaron Burr and Alexander Hamilton sing to their newborn children, who fill them with awe and hope for the future of their nation. Even though I was delivering this toast to celebrate a wedding and not the birth of a child, I wanted to evoke a similar mix of awe and hope — awe in the beauty of the bride and of the day and collective hope for hers and the groom’s shared future together.

When it comes to most writing I do, I tend to hold out until the final days before it’s due to give me a real sense of urgency and pressure. For this, I forced myself to start a few weeks in advance of when I had to deliver this toast. I sat in the hippiest cafe in Cambridge, MA, hoping the divine spirits of Life Alive would be my muses and bring me some much-needed inspiration. Between that and a session at my +1’s apartment about a week or so before the wedding, I had the toast 99% under lock.

I was really proud of what I’d written, but the night before the wedding, I started getting nervous. At the cocktail event after the rehearsal dinner, a few old classmates expressed their excitement for my speech the following night at the wedding reception. Over a year out of business school and not having gone onstage to perform or public speak in a creative capacity since then, I forgot that my reputation at school had been “the writer and storyteller”. So aside from meeting my own high standards, there were other people’s standards I was suddenly considering when delivering my speech the next day.

Sitting in bed, making final tweaks for the toast, I told my +1 how much my old schoolmates’ comments were psyching me out and how I was afraid I wouldn’t deliver something that their expectations. He had the perfect, perspective-oriented reply.

+1: “Do you think the bride will like it?” 
Me: “Yes, no question.” 
+1: “Then does anything else really matter?”
Me: “Uh…no.”

I woke up the next day and spent the morning with one of the other bridesmaids — together, we survived the jabs of a hundred bobby pins in our hair and multiple coats of makeup to withstand the freakish heat wave in San Francisco. Fully varnished with hairspray and setting spray, eyelashes coated in waterproof mascara, we met up with the other two bridesmaids in the bride’s suite and, hair and makeup done, set off to the venue for photographs and final preparations.

They walked down the aisle, the bride and groom gave their vows and kissed, everyone cheered, and at last, the reception began, at which point I began counting the minutes until I was supposed to give my speech. I’m glad I cut the sleeves on the bridesmaid’s dress so I didn’t have visible sweat stains from the anxiety. I didn’t want to rush the wedding because I was having a great time, but at the same time, 10PM wasn’t coming soon enough.

10 o’ clock arrived, everyone took their seats, and someone announced me on a microphone, at which point I stumbled through an introduction and proceeded to sing for the next three minutes.

Given that the bride started crying on the spot, collapsing into the white, feathery pile of her dress, later telling me to send her the lyrics because she had totally lost it and couldn’t pay attention anymore, I think it was a winner.

If only I were 10 months sooner — I could have beaten this guy to going viral:

Thank you for the privilege, Cary. As I’ve said before and will say again, I’d do it all over again for you.