Celebrating the Saddest Day of the Year

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As soon as I stepped into the foyer of the Saddest Day of the Year party, I understood that Ana Tantaros had built a whole world for her event. Blue twinkle lights hung from puffy cotton clouds along the ceiling to look like rain. Darkened hallways gave way to rooms full of people and warm pink and red lighting. Everyone wore a name tag labeled with a dark humor phrase from “I lie to my therapist” to “AI is taking over” or “What even is my comfort zone?” 

Although it’s an annual occurrence now in its 12th year, nothing about this event was usual. And as most of us don’t usually have plans on a Monday night, it felt a bit odd walking into a party at the start of the week. However, Ana created a glorious departure from the norm.

According to pseudoscience and popular culture (which, let’s be real: we listen to and follow more than we like to admit) the third Monday in January has been defined as “the saddest day of the year.” A bunch of factors make up the reasons, including weather, the days since Christmas, and the fact that we’ve likely already failed at our New Year’s resolutions. But Ana Tantaros, a Baltimore photographer and proprietor of Side A Photography, latched onto the idea of making a sad day into a fun one.


Tantaros created a world in which the strangeness of the place and the event itself got conversations between people going. It was as if a Halloween Party and a Valentines Day party got together, but retained only the best virtues: creative eccentricity and cheeky humor.  As a partygoer, it seems her goal is to make the event as exciting and off-script as possible and she adds new elements each year. 

Details of Ana’s party go on and on: a phone in a nook upstairs (an actual phone with a handheld receiver) called a phone downstairs housed in an authentic telephone booth. People from upstairs chatted anonymously with guests downstairs, keeping an odd line of dialogue. The party also included a tarot reader in a darkened nook, signature hand-made cocktails, sad-themed photo booths on both levels, and a “sad caption” wall where partiers wrote absurd captions for magazine ads and articles with colorful markers.

Since parties are typically sold to extroverts, people for whom mingling and relating to each other via sharing stories and high-energy is second nature, the host wanted to appeal to the other crowd for her annual party. By creating her signature “anti-social social” event twelve years ago, she’s opened up a world of possibility for bringing people together under less than ideal circumstances.

Since I bring my camera everywhere I go, I took photos at the event just for fun. I chatted with Tantaros about both the 2023 edition as well as the origins and evolution of the Saddest Day of the Year party. 

See a few photos and our Q&A below.


Mollye Miller: Tell me about how you came up with the idea for this party?

Ana Tantaros: Well, the year was 2006. My journalist friend found a press release by a UK Travel company determining the 3rd (or 4th) Monday in January to be “the Saddest Day of the Year.” My sister thought it was a funny anti-social concept for a party, so we built a lopsided cake, and had a few friends over to hang out with somber music. I brought the idea to Baltimore years later, and began adding photo booths and interactive elements. The party grows bigger and more expansive each year.

What is “The Saddest Day of the Year”?

A UK travel company, Sky Travel, said in a 2005 press release that “Blue Monday” falls on the third Monday in January because of factors including: weather, debt, time since Christmas, time since failed new year’s resolutions, and low motivation levels. [Editor’s note: this hilarious, cantankerous 2006 column from The Guardian is the oldest published evidence we can find online to support the provenance of “Blue Monday”] The date has also been reported as the second or fourth Monday in January too, so I went with that for the party to preserve MLK Day.

Why does this day of the year resonate with you?

I’m interested in ways that people connect authentically, and the concept of gathering together “as is” on a day claimed to be the absolute worst—to mesparks a sense of belonging and oneness. The old, “be kind; everyone you meet is fighting a hard battle” quote always resonated with me.

What do you want this party to mean to people?

I want this party, and any event I host, to encourage interaction among people that may not know each other. Or for there to be enough humorous distraction that anyone can be entertained and feel a sense of belonging. The self-deprecation type of humor (I hope) makes it easy for that to happen.


When did you have the first party?

It was in my sister’s dining room. She hosted 4 of us and a baby in a swing. I remember listening to Radiohead and looking at a pathetic cake and thinking this was the funniest idea for a party ever.

Name a few ways the event has evolved since the first one?

The party started in Baltimore as a potluck because I wanted to make friends and was a lousy cook. I told people to come over with sad-themed food contributions and to invite everyone they knew… I built a homemade photo booth that distributed black and white prints, made a lasagne, stocked the fridge with beer, dismantled the furniture and spent way too many hours on an upbeat sad playlist. I was blown away by the creative food contributionsmisfortune cookies, sad-faced cupcakes, a box of jelly donuts, a pizza with a bottle of ranch that said, “must use ranch” etc. 

Blue Monday Potluck became the “Saddest Day of the Year Party,” and outgrew the house so I started having it at venues. The interactive stationsWall of Woes, Post Secret Mailbox, Caption Wall, Sad song request linehave changed over time to include “Bleak Future” tarot readers, the confessional, the phone booth, etc. Every year I try to add or come up with something new.


What are a few new favorite elements to the night?

The phone booth that calls another floor of the party is basically my dream come true. Mike Bowman of Formstone Castle built it and I got the phones from Steel Owl Productions. I miss the analog, tactile days when we set aside time to talk on the phone and I love incorporating that activity in a party setting. I have ideas on how to further the installation with more conversation prompts and/or codes people can dial to listen to pre-recorded messages.

At the most recent party at No Land Beyond, what was your favorite part or surprise of the night ?

OhEASY! When I was waiting in line for the tarot card reader, I saw a pen and paper coming out of a slot in one of the structures I put in one of the rooms. This structure was meant to house the tarot reader, but turned out to be too small, so it was basically an empty house with a door slot, like a mailbox. Two girls were inside and had written questions on pieces of paper, and were handing them through the slot with a pen. Mine said, “when was the last time you cried?” I wrote my answer on the piece of paper and when I returned it, they handed me a carrot through the slot. I love it when people take initiative with the party and either dress in character or host their own experience for other people to participate in. I want more of that!

Tell me about the “antisocial social” aspect. How’d that develop?

Hmmm. I think everyone has times of feeling social and anti-social, and I like having a party where you can be either or both!

You seem to be very anti-boring! What do you dislike about traditional parties and socializing in general?

I’m an off-the-charts extrovert, but don’t always want to talk to peopleespecially when the conversations are empty and the questions are generic. Larry David has a good bit about being at a party and just looking for exits, “Uhhh, I have to go to the bathroom! Uhhh I gotta get a drink … help!” I do feel that way sometimes, and want for there to be a wonderland of distraction that I can move through easily, and strike up a conversation with anyone about what I see, so that’s what I’m trying to do!


What (if any) new activities do you want to add to the party in the future?

To be completely honest: I’d like to get funding to hire artists to build interactive elements (like the phone booth) that people can move through and engage in. Sort of like my favorite museum growing up, the Please Touch Museum. But here the things people do in one space would manifest in a different room or area of the party, and the people receiving it can respond. And I’d like there to be small social tasks—like, do these five things, receive a free drink ticket, give that ticket to someone you don’t know, etc. 

But the first part is building a team to brainstorm it with me. (I hope anyone reading BmoreArt who wants to help me make more creative parties that spark inspiration, thought and conversation will jump on board and help me brainstorm the next one!)

What’s your relationship with No Land Beyond? What do you love about their concept and event space?

No Land Beyond’s mission and outlook falls in line with what I want to achieve with these parties. They engage people and welcome groups of friends to connect through activity and gameplay. I’ve had the most interesting conversations with different people at that bar.

You’re a talented photographer with a successful business, Side A Photography. How does the party fit in with your photography life? The photo booths at the party are awesome and very on point.

Thank you! Side A Photography is primarily an event photography company with a series of photo booths. This means, I go to parties ALL THE TIME! Only, I’m behind the scenes observing, capturing, and following the actionnot necessarily participating in it.

My experience has made me want to further explore and enhance the party-going experience to find ways that people genuinely connect and engage. I built my first photo booth in 2009 for this reason, and it worked! People were cramming into a wooden box with people they didn’t know, while other people called out poses and handed them a prop to hold. I find photography a powerful tool in not only documenting but also creating social connection.


Please share anything interesting you’d like to add about “The Saddest Day of the Year” party, including a story from this year if you wish!

Hmmm… Well, this is the ninth party. My favorite memory is when I set up what looked like a giant wooden lemonade stand and wrote the word “confessional” on it without any instructions.Throughout the evening, people would sit on either side of the confessional, and I received the greatest compliments from that experience. Apparently, there was one guy I didn’t know who sat in that confessional for most of the evening and listened to people. They said his presence was so calming and they felt so glad to talk to him. I like it when things take form on their own.

Oh, and meant to ask about the name tags. Tell me about how those started and your process for creating them.

My sister Elisabeth came up with that ideathe original party idea sparker. I now have 400 of them for this party and have been making them for every party I’ve had in Baltimore. It is a great way to start a conversation, and fun to read and choose one that strikes a chord with one’s personality.

What name tag did you pick this year and/or what was one of your favorites you saw walking around the party?

Oh my gosh… those name tags are a real ego booster because I think they’re so funny (and I wrote them). Mine was “the human condition”… which I felt was a good tag for the host. I enjoyed seeing “Linear thinking? Not my strong suit” and “Lone Wolf.” I saw someone walk over to the table and immediately pick the first tag they saw exclaiming, “YES, THAT ONE,” proudly peeling the sticker back and slapping, “I regret my tattoo” on their vest pocket.


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