I Tried To Crash A Valentine's Day Wedding At The Plaza Hotel

Photo: Sean Pavone | Shutterstock, ozgurcankaya, Jacob Lund | Canva 
Crashing wedding at the Plaza

Every year without fail, a few weeks before this so-called dreaded holiday also known as Valentine's Day, my coupled-up friends start asking in a very somber, concerned type of way: What are you doing for Valentine's Day?

This year, I wanted to have something epic to spit back at them, something that would veer the focus away from me flying solo on a day when it's tragic to do so.

So, I decided I'd crash a Valentine's wedding at The Plaza Hotel in New York City.

How did I know that there would even be a Valentine's wedding at The Plaza on Valentine's Day?

Valentine's Day fell on a Saturday that year, and with only 52 Saturdays per year for brides-to-be to choose from, I had a strong feeling that, on the supposed most romantic night of the year, some bride somewhere had the sense to book the prestigious New York venue for her big night.

But obviously, I needed more information before I was to embark on Operation: Crash The Plaza.

RELATED: 5 Wedding Planning Behaviors That Can Predict The Success Of Your Marriage

Here are the 4 phases:

Phase 1: Ask the experts

Are there experts at wedding crashing? In the professional sense, no, but I was able to talk to a few people in my network who had successfully pulled off blending into a wedding party on a stranger's big day. They graciously offered me a few valuable tips. My friend Steve was particularly helpful since he works in the hotel industry in New York City.



I should mention that almost all of these sources urged me to try a different venue but I had my eye on the prize.

"They're sharp at The Plaza," Steve warned me, "Be on your toes!" He also coached me through calling The Plaza to fish for information on the wedding. I followed his lead and made the call a week before the big day.

"Hi, so sorry to bother you! I'll be attending a wedding at The Plaza on Saturday the 14th and just wanted to confirm what time would be most appropriate to arrive. We'll be surprising the bride's family, we haven't seen them in—"

"Hold please," the receptionist told me.

I waited, got someone new, and recited my speech word for word.

"It would be best for you to get in touch with someone from the event," the receptionist told me, and not wanting to sound suspicious, I thanked them and hung up.

RELATED: 5 Things I Did Right At My Wedding — And 3 Things I Did Wrong

Phase 2: Assemble a wedding party

Even Vince Vaughn didn't crash weddings solo: he needed a partner in crime (P.I.C.) to help him pull it off. Since having a P.I.C. had worked out well (mostly) for Vince in Wedding Crashers, I enlisted a few people who were also free on V-Day and were up for an adventure. Our wedding crasher crew ended up being five people total: two girlfriends, and two guyfriends. A week before the wedding, we spent a night getting our stories straight on how we knew each other (and the bride and groom) and even made up some fun alter egos to go by, just for kicks.

A few days before the event, we took a walk through The Plaza to figure out exactly where we were going, which entrance would be the closest for us to enter to get to the Grand Ballroom, and what stairways (if any) would lead us up to the venue in case the main entrance was blocked off.

When it came to wardrobe, we followed Steve's advice and dressed to the nines, but not in a way that stood out. His exact words to me for pulling off this look were to "occupy the mind of a socialite rich girl who just threw on one of her dresses for this wedding she doesn't want to attend."


Phase 3: Convince everyone we won't get arrested

A curveball was thrown into my master plan when it was brought to our attention that crashing a wedding at The Plaza is an offense punishable by jail time. The Grand Ballroom is private property and we'd be trespassing, making the crime a misdemeanor, punishable by up to a year in jail. Also, we were planning to do this on a holiday weekend, so if we did get locked up we wouldn't be able to go before a judge until Tuesday.

Could we survive two whole days in the slammer?

According to Steve, although he'd seen crashers at events at his hotel before, no one who wasn't being belligerent about not leaving had ever been arrested. His advice? If we end up getting caught, stick to the story that we ended up at the wrong event (apparently it happens all the time in New York City) and get out of there.

We decided to take our chances.

RELATED: How I Got The Wedding Of My Dreams By Calling It All Off

Phase 4: The big day

Wedding Crashers came out in 2005, way before Instagram's geo-location tag made it all too easy to find out what's going on at any given wedding venue. I refreshed The Plaza's geo-tag furiously the morning of the 14th until I found my first clue around noon: a post from a bridesmaid, geo-tagged at The Plaza, of the bride's crystal bouquet.

Photo: Secret Garden/Pexels


I went through the bridesmaid's Instagram to try and locate the bride, hoping for a last name to use when we all arrived just in case we were stopped, and even tried to find her via Facebook on the bridesmaid's account but I came up empty.

As the afternoon went on, more photos were posted, and we realized we were up against a new challenge when it came to blending in: the bride and groom, as well as most of their guests, were all of the same ethnic backgrounds ... and we were not. Which made us much easier to spot.

We worked together to figure out how we were going to avoid standing out and even talked about showing our faces at the cocktail hour so that our appearance later on during the reception wouldn't seem so random. Then at about 6 pm, that same Instagram user who had been guiding our plan gave us a run for our money: she posted a reception photo at a different location.

Now, we had no idea what we'd be walking into when we headed over to The Plaza. We kept refreshing the geotag up until we left for the venue, but no dice.

We got to The Plaza just before 10 pm, hoping that the wedding would be in full swing by then. When we all turned the corner to the hallway leading to the Grand Ballroom, we hit another wall (literally): It was closed off.

At this point, we opted to split up. I went with one of the guys to find out what was happening in the Grand Ballroom, and to figure out how we could get the rest of our crew in. We went downstairs through The Plaza's dining area and came across another smaller event that was just finishing up.

"Can I help you?" one of the people breaking down the event asked us.

"We're just trying to get back up to the hotel," we explained.

"Are you staying at the hotel?" he asked.


Luckily he bought it, and we were given directions that conveniently led us past the area that had been blocked off. We walked up the stairs and got on the elevator that led to the Grand Ballroom.

It was the longest elevator ride of my life.

The doors opened in slow motion ... to reveal an empty ballroom.

No bride had my same genius "Valentine's Day at The Plaza" wedding idea. Seriously: The Grand Ballroom, at The Plaza, was empty on Valentine's Day. 

I later learned that SNL's 40th Anniversary after-party was being held there the next day, so perhaps that's why nothing was scheduled for Saturday. We met our fellow crashers at the hotel's bar and broke the news, which they took pretty well because we were now all dressed up with no place to go. But we made the most of it and ultimately ended up at a dive bar — still decked out in our evening attire. We even spent the night sticking to those fake personas we'd worked so hard to come up with.

Some nights are more about the journey than the destination, and this Valentine's Day proved to be one of those times. Even though we weren't successful, I had a blast spending the last few weeks thinking about how we'd get in, planning out an outfit, and coming up with ridiculous alter egos to stick to. I'd take this whole experience over some cheesy Valentine's Day date any day.

RELATED: Bride's Wedding 'Ruined' By Woman Who Said She's 'Surprised He Married Someone Like You' — & Then Smashed Her Cake

Alex Alexander is a pseudonym. The author of this article is known to YourTango but is choosing to remain anonymous.