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The ‘craziest wedding year of all time’: A photographer’s overbooked, overwhelming 2021

Many couples rescheduled their nuptials for this year, but still had to scramble to prevent coronavirus outbreaks

Michael Cassara photographs a Sept. 11 wedding at Flowerfield in St. James, N.Y. (Michael Cassara Photography)
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If 2020 was the year of wedding-postponement misery, 2021 was the year of sweet, sweet delayed gratification — of long-planned events finally coming to fruition and bursting out of every venue that could possibly host one. Couples were scrambling to lock down vendors, prevent coronavirus outbreaks and manage their ever-fluctuating expectations for guest turnout. Guests themselves were exhausted.

Michael Cassara, 35, is a wedding and lifestyle photographer based on Long Island — emphasis on the “wedding,” as nuptial celebrations are famously big and fancy affairs in the region and make up about 85 percent of his annual business. Photographers bore witness to 2021 weddings in all their cathartic, frenetic, superspreading glory — the “craziest wedding year of all time,” Cassara says.

He spoke to The Washington Post about his experiences, including shooting amid social distancing requirements (spoiler: you should make it look as normal as you possibly can), dodging coronavirus droplets in big crowds (a strategy that worked until it didn’t) and pulling way more “doubleheader” weekends than usual.

The following has been edited and condensed for clarity.

His wedding calendar was packed

I shot 46 weddings this year. A normal year is around 30 weddings. Twenty-four of my weddings this year were rescheduled from 2020, and I had already booked 18 weddings for 2021 before covid hit.

My busiest month was September, where I had 10 weddings in four weeks. One weekend at the end of September, I had two weddings, one at Pellegrini Vineyards, the other at the Vanderbilt Planetarium [more than an hour’s drive from each other]. I was driving all over the island, back and forth. I probably did 400 or 500 miles of driving that weekend.

Some were second-, third- and fourth-time’s-the-charm weddings

The most postponements I’ve seen was, I think, three: rescheduled from May of 2020 to July 2020, back when everyone was like, “Yeah, we’ll be out of this in a few weeks,” and then they went from July 2020 to May 2021, then decided in May to reschedule again to November.

The best was the weddings where they had these Etsy signs saying, like, “Our first date! Our engagement date!” And then, “Our wedding date,” crossed off. “Our second wedding date,” crossed off. And now, “Our third wedding date.” I was cracking up. You almost have to laugh at that point, right? You finally made it.

There was double the anxiety this year from my clients. I would get texts from my brides ahead of the wedding, like, worried about the weather. You kind of calm them down, beforehand and throughout the day, and that’s part of the job.

The year began with pre-vaccine, heavily-restricted events

In January, the first wedding I shot of the year was probably the most stringent. There were “dancing squares in effect, where you could only dance with people in your household or the table you were at. The couple could move around the dance floor if they wanted to, and go table to table, but they couldn’t have the guests in the middle of the dance floor. The venue was very strict about it. They were monitoring the whole time. If you did get up from the table, it was only to go to the restroom. You couldn’t go to the bar; servers had to serve you alcohol.

There were a few members of the bridal party who were immunocompromised, and they wanted to wear their masks for photos. But what you try to accomplish as a photographer is: How is this going to look as normal as possible? The couple is going to look back in 10, 15 years and forget there was even a pandemic going on.

But weddings changed after vaccines arrived

Right around April or May, weddings started getting back to normal. I would say 75 percent of weddings I shot this year felt like weddings in 2019. One required that vendors be vaccinated and wear masks this year, but the majority really didn’t care about the risks as much as you would probably think.

Weddings went hard this year. You could tell people were cooped up for a year, and they wanted to get out and party and let loose. This year, I’ve seen everything from people mosh-pit stage-diving off speakers to one wedding where they brought in a gigantic jump rope and the bride and groom were jump-roping. I’d never seen that before. I’ve had grooms break-dancing, guests break-dancing. I’ve seen a nine-foot dancing robot come in, with LED panels and smoke cannons.

There were day-of nightmares

I do recall bridal party members missing the wedding because they had covid. And parents of the bride or groom who had covid but they were adamant about coming to the wedding. They were forced to not come, and that caused a little bit of drama. I’ve also seen other vendors who’ve had to drop out a day or two before a wedding day. Florists, for example: The couple’s floral arrangements were compromised.

I didn’t hear too many stories, at least on Long Island, where the bride and groom got covid, but I heard a few — like the day after, they got tested because they weren’t feeling well and it ended up they probably had covid the day of their wedding. Thankfully that did not happen to me.

When anti-vaxxers want to come to your wedding

And the deluge took an emotional toll

It took a heavy toll on a lot of my friends and a lot of other vendors. My clients were phenomenal, absolutely phenomenal. But with a lot of people who were inquiring, or were scheduling their dates, there was a high level of demand, especially from parents of the brides and grooms. At some moments, it was almost like they didn’t really care that you’re a small business, or that you’re busting your butt for your client. They want results, and they want them quickly. Meanwhile, we were doing double the work that we would normally do for a calendar year.

I know a handful of other photographers who — this broke them. I’m relatively new to the industry, in terms of being a full-time wedding photographer. So I think I still have my mental sanity. But others, they’ve been in this for 20 years. And they’re just like: “Yep, I’m good. I’m done. I’m checking out.”

Not to mention a physical one

We call it the wedding hangover, or vendor hangover — where your body just decides to say, like, “You’re done.” Basically, you just shrink into a chair and collapse for the whole day on Sunday. This year, I invested in a massage gun for my muscles. Great investment there.

I caught the coronavirus at my second-to-last wedding of the year, the one wedding where I probably got a little lax with my mask. Four people got it at that wedding, and it forced me to miss my last wedding of the year. Thankfully, I have a very capable team of photographers that filled in and did a phenomenal job. But in the world we have today, you almost have to plan for that to happen.