Shakespeare, We’re in Love (At Christmastime)

No holiday collection would be complete without a twinkle-light rom-com, like the kind that inhabits the airwaves from October to January (and pops up most Fridays on the Hallmark channel). We all know the movies I’m talking about—big-city gal goes back to her hometown before Christmas, falls in love with the hunky townie from high school, and climaxes in a single kiss as they go for a stroll after the town tree lighting. The male lead is usually exceptional at just one thing: running an inn, construction, app development—hell, I’ve even seen one where the guy was an expert at bird-watching. There’s never any sex and rarely any gay people, but the holiday season fills every inch of the television screen as the beats play out. It’s magical, predictable, like visual Xanax.

Each one is almost exactly the same, and yet every year, there are more and more of them. Some people loathe them, while others like me tune in to each one the machine wants to feed us. Sometimes I’m not even sure if I’m watching one I’ve seen already or if the familiarity of Lacey Chabert building a gingerbread house is warping my brain waves. Watching feels like a warm, familiar hug from an old friend. You know you’re settling in for a few hours of Christmas cheer, with no real-world craziness seeping in. It’s barely even evident what year the films are made because they’re meant to be evergreen. Watching a Hallmark or Lifetime holiday movie from 2003 is essentially the same experience as watching one from 2023.

Despite the fondness I have for these made-for-TV movies, I can recognize the shortcomings. Although there is considerably more diversity in the cast of characters on-screen nowadays, they’re not exactly known for the gay representation. I can count on my hands how many of the literal hundreds of original movies from the past two decades feature LGBTQ+ characters, let alone LGBTQ+ lead characters (fortunately, it is getting better every year). Since there are so few people highlighting my big gay experience, I thought I would do it here in this book. If you don’t see something, write something… That’s the saying, right? Maybe I’m getting my wires crossed, but I’m here and I’m queer, and I’m ready to sweep you off your cynical feet with my own twinkle-light romance!

Fortunately, I don’t have to work too hard to come up with a plot. One of my first (gay) relationships was a twinkle-light romance. Big-city gay falls for small-town homosexual over the holiday season! Technically, we were both in the same city, and the other gentleman was not a hunky construction worker and instead a trained (still hunky) Shakespearean actor, but the beats are (mostly) the same…ish. Now on to our meet-cute!

My first winter living in Chicago proper was tough. Coming from Ohio suburbia, I had left my network of friends behind to make it in a big city, but I wasn’t quite prepared for the extreme weather (Illinois is much windier than Cleveland). I worked my ass off, taking on any job I could to pay my ridiculously high rent and waking up when it was still dark out so I could catch the train to the office where I temped. The cold winds as I waited for the red line were brutal at 6:00 a.m. It didn’t matter how many pairs of long underwear or gloves I wore, waiting for the train sent my body into shock. So much shock that I had a bout of pneumonia that left me briefly hospitalized in month two.

When I finally recovered in late November, I was ready to move onward and upward, determined to leave the bad luck behind me and adjust to my new city. I invested in another layer of long johns and settled into work as a temp at a real estate office. In hopes of being hired full-time after my temp contract ended, I agreed to overtime and volunteered to run extra errands for my boss, the evil Mr. Tiskman, a man who reveled in bulldozing trees for large industrial complexes, a man who survived on energy drinks and extramarital affairs.

“Danny, you’re into artsy stuff, right?” Mr. Tiskman asked one afternoon when he overheard me listening to the Wicked soundtrack at my desk.

“I take some improv classes downtown on the weekends, but—”

“Great, my daughter’s school is looking for a director for her Christmas play. The person they had was caught with booze at the rehearsal.”

There was no question mark attached to his statement, so I was slightly confused when he seemed to suggest I was destined to take charge of this school play without much incentive. Powerful men like Mr. Tiskman have a delusional self-confidence, which always works in their favor. It was a delusion I envied as the meek and cowering closeted twenty-two-year-old I was, trying to survive in a big city that favored grit.

“Are you asking me to…?”

“Take over the school play, yeah. My wife is driving me crazy about it. I can’t hear about it anymore, so please, just do the last couple of rehearsals, and I’ll pay you hourly under the table.”

“I’m not, like, a theater expert. I’m still in level-one improv, and I barely have any free time. I’m still living out of my suitcase after four months!”

“You’ll be fine. I know you listen to that Broadway crap, and the kids are all twelve and under.”

“Wicked is not crap, it’s—”

“My wife will email you details,” he said.

Before I could launch into my explanation of why “Defying Gravity” is one of the greatest American songs of all time, Mr. Tiskman was gone. And days later, I was walking into a private school gymnasium and meeting with Mr. Tiskman’s wife, who introduced me to twelve kids under the age of twelve, all of whom were sugared up from the red velvet cupcakes that the previous director had sent as an apology for no longer being able to work with them due to his drinking problem.

The first rehearsal was a complete blur. The students were doing a Gift of the Magi-esque story about a daughter selling her bicycle to buy her dad a hammer and the dad selling his hammer to buy a bike seat for his daughter. Some of the young children were playing grown adults, while others were children. They claimed to have a script memorized, but no one had a copy of said script, so I had no idea if they were actually reciting the correct lines (and every young mind had a differing opinion about what the dialogue was). I spent most of that rehearsal staring in awe at the chaos around me. I imagine this was how Ryan Murphy felt on the set of Glee.

As the kids were picked up by the parents two hours later, I made plans to visit a bar to unwind. I understood why the previous guy was liquored up all the time; these children were exhausting. Although I didn’t have many friends in the city, that wasn’t going to stop me from getting the drink I’d earned. While seated solo at my favorite watering hole, a place in the middle of a holiday karaoke night, I spotted a cute guy, also by himself, reading. With a Shakespeare play in one hand and pen in the other, he was making notes as he scanned the pages, sipping his hot toddy topped with whipped cream in between underlining. Shockingly, he was able to concentrate as a smattering of out-of-tune homosexuals sang Judy Garland, but alas, he was in the zone, never once looking up to see who was rocking around the Christmas tree. Normally, I would’ve ignored him, spent time on my phone scrolling through Twitter, but something took hold of me. Perhaps it was some reverberating chutzpah from the beautiful trans woman who was singing “Last Christmas” on key.

“I though the point of a bar is that you go when you’re done working?” I shouted from a few seats over.

“Work is pleasure for me,” he replied, finally looking up from his book.

“Shakespeare is pleasure?”

“If you do it right.”

I took a sip of my vodka soda and moved closer to the mystery man who looked like a budget, less-super-but-still-gorgeous Henry Cavill, a ballsy move I chalked up to my last vodka soda. The man put his book down and confidently looked into my eyes.

“I’m Jesse.”

A beat went by before I realized he wasn’t going to ask my name, a power move to match my moving seats.

“I’m Danny. Nice to meet you. I never could get into Shakespeare, too hard to understand.”

“I’m an actor, so—”

“No way! I’m an actor too!” I bragged.

At this point, I never anticipated this man to be more than a possible make-out before bed. My audacious flirting aside, I had never done more than hook up with a guy. I certainly never entertained the idea of a relationship. Flirting was always a means to an end that included sex without the romance and then never speaking again unless it was to kiss after a night of drinking.

“You’re an actor, but you don’t know Shakespeare? It’s the foundation of acting!”

“You’re one of those actors—”

“What kind of actor are you?” he asked.

“Well, I’m teaching right now. Technically, I’m directing a play,” I replied, giving myself entirely too much credit. Jesse didn’t need to know I was barely in charge, my students were under twelve, and I was less hired and more forced by someone who was (sort of) my boss. I was the production babysitter.

“If you’re teaching, you must know Shakespeare. I know of a class you could take—”

“I’m so busy right now. I wish I had time for a class,” I said.

“You’re at a bar, alone, at eight o’clock on a Tuesday, and you’re young. You don’t have time?”

“I mean, technically my nights are free, but I’m—”

“Good. I know of a class, one night a week, seven thirty to ten.”

“No, I, uh, I mean—” I was too slow to find a way out, so I was thrilled when he changed the subject.

“You going to sing tonight, kid?”

Kid? He was barely thirty, a handful of years older than I was.

“No, no, I don’t sing. That’s my gift to society: not singing.”

“So you don’t do Shakespeare, you don’t sing, and you still consider yourself an entertainer?” he asked.

“When you say it like that, I mean, uh, um, I want to be—”

“I suppose those who can’t do teach,” he said with a smirk.

“It’s not like I’m scared of those things. I just—”

“Sure, whatever. Obviously you’re scared.”

“I’m not scared!” I asserted, raising my voice to levels I never had before.

“You’re scared. Everyone can sing a little. You’re just scared to.”

I was determined to prove this man wrong out of spite. How dare he call me scared! I stormed up to the stage, a small platform covered in tinsel and garland, whispered into the ear of the older gentleman in drag running the amateur singing hour, and prepared to blow everyone away with my out-of-tune singing. The opening chords of the melancholy “Miss You Most (At Christmastime)” by Christmas queen Mariah Carey began to play. After just a few seconds, it was evident that my voice was less 1994 Mariah and more dying cat. The worse I got, the more the people cheered. I felt like Cameron Diaz in My Best Friend’s Wedding, getting happier and happier the worse I got. The boos mixed with cheers as I wrapped up the holiday ballad with a smile. When I looked over at Jesse, I noticed he was smiling too, shocked at just how terrible I was at singing and somehow charmed by my tonelessness.

“I told you I wasn’t scared.”

“See what happens when you get out of your comfort zone?”

Even though I’d come out on top, he’d somehow manipulated the act into a win for him. It was impressive and would’ve been more so if he didn’t have whipped cream on his nose from his hot drink.

“Looks like you’re the one who’s a little too comfortable,” I said, pointing to his gorgeous nose.

“Excuse me?”

“You have whipped cream on your nose.”

Rather than wipe it off, Jesse smeared it around his cheeks. His confidence was as contagious as it was infuriating, and it was enough to convince me to show up to this Shakespeare class he raved about.

“You really don’t embarrass easily, do you?” I asked.

“Life is embarrassing. Might as well lean in.”

“So where is this stupid Shakespeare class you were raving about?”

“Here,” Jesse replied, grabbing my arm in the process and writing a phone number on my skin with his pen. “Call Susannah Kline. She’ll save a spot for you. First week is free. And don’t call it stupid ever again.”

“Will do, old man,” I said, matching his energy.

Jesse stood and began to put his coat and scarf on.

“Leaving already? What about your number—” I couldn’t believe the words were leaving my mouth. I had never asked for a number before!

“I’ll see you around,” he replied, keeping his digits closer to the chest than I would have liked. He took the candy cane garnish off his empty hot toddy and started to make his way to the door.

“Wait! You still have whipped cre…never mind.”

Jesse walked back up to my chair, reached across my chest for a cocktail napkin, so close that I could smell his peppermint breath. He wiped his nose inches away from my own face; I could see the creases in his lips, the stubble on his chin.

“Did I get it all?” he asked, looking deep into my soul with his stunning hazel eyes.

My heart was racing, wondering if our lips would meet for a kiss.

“You got it all,” I said as he moved away from the moment.

“I’ll see ya, kid.”

Jesse’s presence left me with a hangover. He was infuriating and intoxicating at the same time. I HATED this man but also fell madly in love.

Less than a week later, I showed up to the first Shakespeare class at the home of Susannah Kline, a woman who looked exactly like she taught drama classes out of her home. The Charlie Brown Christmas tree she had near the window obviously had been up all year, but she’d decided to finally turn on the lights after Thanksgiving. A handful of twenty- and thirtysomethings gathered in her living room. Kelly, a young woman I knew from the building where I worked, sat next to me.

“Hi! Omigod, you work on Monroe, right? I think you’re in—”

“Yeah, I thought you look familiar. I see you at the commissary sometimes. I’m Danny.”

“Kelly. Nice to meet you! I’m an actor. I mean, I work as an assistant, but it’s only to pay for classes like this. Susannah is the best!”

“I’m not really into Shakespeare, but I met a guy who recommended it,” I said.

“You don’t understand—she is the best. People come from all over the country to work with her.”

“For Shakespeare?”

“Yes! No one better in the country.”

“Hm. Cool, I guess.” I shrugged.

Other people filed in, each seemingly more excited than the last to be here. I started to get a contact high from all their iambic pentameter buzz.

“Omigod, omigod, omigod!” Kelly said as her cheeks turned red.

“What? What’s wrong?” I asked.

“I can’t believe he’s here!”

“Who? Who’s here?”

“He plays Edward the Third! I just saw his play last night at the Chicago Shakespeare Company!”

I looked up and there he was…

“It’s Jesse Mendelson!” Kelly exclaimed. The rest of the room gasped as Jesse made his way to Susannah and gave her a big hug. The energy completely shifted; the crowd treated him like royalty.

I was horrified. Just the other night, I was bragging about being an actor and an acting teacher, all to a man who was seemingly one of the greatest living Shakespeare performers.

“Jesse is one of the greatest living Shakespeare performers!” Kelly confirmed.

“Everyone sit, everyone sit! We need to get started! We have a new student joining us, but more importantly, I’m sure you all know Jesse Mendelson. He’s in town from New York, taking a hiatus from his hit Broadway shows to do Edward III at the Chicago Shakespeare Company, and he agreed to come by to show us a few things,” Susannah said to the room.

“Hi! So nice to meet you all. Susannah taught me back when I lived here, and I always try to make it to her classes when I’m in town. This work is my passion, and I look forward to spending the next couple of hours showing you all why.”

Everyone looked at Jesse as if he were Julia Roberts showing up at a Walgreens. Part of me wanted to run out the door and never look back; the other part of me wanted to stand up and brag about knowing Mr. Popular. Before I could decide—

“Danny! You made it. Good to see you!” Jesse said with a wink in front of the entire group.

I melted like a snowman in June. His cockiness was softened, and I was intoxicated by his influence. I was famous by association.

“Omigod, you know Jesse?” Kelly whispered.

“Kinda, sorta, maybe,” I said.

The next two and a half hours were just as much of a blur as my first play rehearsal with the kids; I spent the entire time trying to figure out if I should stay behind to talk to Jesse or sprint out of that drama house as soon as the clock struck ten. The choice was made for me when Susannah wrapped up class by calling for me to stay behind. Something about payment and logistics, since I was joining a group that had already had a week together.

Kelly and most of the others slowly filtered out of the home, and I sat idle while Susannah chatted with one last student who needed some help with his Othello monologue. Jesse ran to the restroom and came back to sit in the empty chair next to me with an annoying grin he had from so many people kissing his ass all night.

“You learn something, kid?”

“Ya know, I don’t think I’m that much younger than you.”

“You sure do act like you’re younger,” he countered.

“How dare you? You’re the immature one who didn’t even tell me you were some big Shakespeare guy.”

We playfully argued like Sandra Bullock and whatever male lead she is starring alongside until Susannah was ready to chat about payment. I hated him even more than I had at the bar, and yet I desperately wanted him to like me. It was pathetic. I was pathetic, but the heart wants what it wants, and mine wanted to prove I could win over this jerk who was also impressive and kind underneath his frustrating (and gorgeous) exterior. My proximity to Jesse got me a friends-and-family discount, so I was able to spend the next three weeks in December learning about Hamlet and company in between kid rehearsals and busy office work during the day. I loved it, even though I was also completely exhausted from all the personal growth I was doing.

Jesse invited me to attend the opening night of Edward III in early December. He offered me two tickets, the best in the house, and Kelly tagged along. He was brilliant; I was so mad. Up until the play, I’d thought maybe he was just okay, that maybe the people raving about his work hadn’t actually seen him perform. Unfortunately, even I could tell he was great. Seeing him onstage was breathtaking. One show turned me into a Shakespeare junkie; I couldn’t get enough. I got to work memorizing a monologue for class, and I even did some fancy acting exercises I learned with the kids as a rehearsal warm-up. Seeing eleven-year-olds do a piece from The Tempest was tough, but I became obsessed with the deceased playwright. There was a child who was originally supposed to play a shop owner in the school play, and I turned his dialogue into iambic pentameter (which ended up sounding more like One Fish, Two Fish, Red Fish, Blue Fish).

The whole time I got to know Jesse (and Bill Shakespeare), I was still closeted. No one in my life knew I was gay. I snuck out to queer bars in the city alone, and I didn’t personally know many folks in the city outside the crowd I was getting to know at work and my extracurriculars. The people closest to me were back in Ohio, and my fear of coming out kept a wall up when I met others, preventing me from getting too close. That all changed, and Kelly was the first person I officially came out to, and it was largely because of my crush on Jesse. She was so impressed that I knew him, it was easy to let her know it was potentially romantic. I was empowered by it.

After Jesse’s premiere, he asked me on an actual date-date, and I panicked. Flirting at a bar or after an acting class was one thing, but a real date seemed dangerous! Jesse was so comfortable in his skin, and I realized that had rubbed off on me. It’s why I had managed to get onstage and sing Mariah in front of strangers at holiday karaoke, it’s how I found out I had a love of Shakespeare, and it’s why I said yes to a night out on the town with a man who was moving back to New York after the holiday season.

Jesse told me that the theater production put him up in a hotel downtown, and he wanted to know if I would come and have dinner with him. Our date night rolled around. I put on my finest wares and took public transportation to the hotel. He met me downstairs, and we had a nice dinner nearby at a quiet pub—the kind of place that only Chicago does right. After our plates were cleared, Jesse grabbed my hand to hold it. My whole body tensed, worried about what would happen when our waiter saw me holding the hand of another man. Before finding out, I yanked my fingers away from him and put my hands under the table. How was Jesse so comfortable being himself in public? Not just himself but romantic! With another man! It was astounding to me.

We finished our cocktails pretty late, and Jesse asked if I wanted to go for a walk around the city. He knew of some cool areas I’d never been that he wanted to show me. We walked around well after midnight and began to explore the streets that were covered in snow from earlier in the week. In urban areas like Chicago, people are always out and about; nothing ever quiets down too much. As we walked through the beautiful downtown, he grabbed my hand again. He grabbed my hand again! Like, he held my hand. In public! We weren’t even surrounded by walls in a dimly lit restaurant. Not only that, but I also held it back this time, and I felt happy inside!

The night turned out to be the first real date I’d ever had. Those evenings in high school and college with girls I pretended to have a crush on were nothing like this; this was what romance was supposed to feel like. It was butterflies and exhilaration. We walked hand in hand under the city sky, his skin keeping me warm. We stopped on a bridge overlooking the river that was lined with twinkle lights, and it began to snow.

“Isn’t the snow magical? The way it covers all the dirt and grime on the streets, making everything look fresh and new,” Jesse said as he looked out over the frozen water.

The moment was too special for me to reply verbally; instead, I surprised even myself by grabbing Jesse’s red flannel shirt, pulling him close, and kissing him as snowflakes fell, melting as they seeped between our lips. A group of carolers walked by, singing and jingling some gold bells, but I wasn’t scared at all. The fear of someone finding out my little gay secret was nothing compared to the thrill of falling in love for the first time.

We had two more amazing weeks together. Jesse came by the school play I directed; he coached me on my Measure for Measure monologue for Susannah’s class.

“Thus stands it with me! Upon a true contract…”

“No, no, no! There’s a rhythm!” he said frustratingly from the comforts of a luxurious penthouse suite bed that his producers paid for.

Jesse had to go back to New York, and I arranged to spend Christmas with my family back in Ohio. We made plans to see each other in the new year, me visiting NYC and him letting me know when he could make it to the Windy City, but the truth is life isn’t always like a picture-perfect Hallmark movie. If it were, the credits would’ve rolled after our first big-city kiss. We never saw each other again. Our relationship wasn’t meant to last, but he was still one of my great loves because he taught me to love myself. He showed me bravery and romance, confidence, and the beauty of a first kiss in the snow.

My love of Shakespeare and the written word continued; plus, I got the full-time contract at the real estate office thanks to the school play going off without a hitch. There were other men ahead for me in the city too: a cowboy, a pilot, and a bartender. I only stayed at the job for a little while before moving to another state myself, something I heard Mr. Tiskman’s wife did too, with a man named Robert (Kelly would update me every few months about all the drama back in Chicago).

A handful of years after my time with Jesse, I was dating someone new, the guy I’m with now, a man I would’ve never met if I hadn’t spent that winter with Jesse getting comfortable in my own skin. I decided, like William S., I would write my own little sonnet to my lost love Jesse in the form of an email. It wasn’t quite as poetic as Romeo and Juliet or Othello, but it was from the heart…

J,

I’ve been meaning to write you for a while, to thank you. I know we barely got to know each other, but you came into my life at a time when I needed it most. I didn’t think I would be able to fully come out. I struggled for years to be myself, and I was instantly attracted to your confidence because I had none. You seemed so sure of yourself, and I had never known a gay person so comfortable in their own skin. Aside from the amazing example you set, you introduced me to Susannah and the language of Shakespeare. My eyes were opened to so many new things. Even though I quickly understood that we wouldn’t be more than friends, I’m grateful for the few nights when I was in a world I had never been. There was a moment when you grabbed my hand when we were walking down the street, a moment I’ll never forget. Your company was great, but more importantly, I realized I could be myself in a world I thought was telling me to be someone else. You did more for me than people I have known my entire life, and for that I thank you. My instinct is to apologize for this hokey message, but instead I’ll try and live in my bravery. I wish you the best of luck and hope for only great things in your future.

“Hear my soul speak. Of the very instant that I saw you, Did my heart fly at your service.”—The Tempest, Act 3, Scene 1

With respect and love,

Danny

That was the end of our love story, a love story that laid the foundation for the romance I was meant for, and it showed me that the heart can fly.