On Stage at Cherry Lane Theater: A Proposal that felt Straight out of a Dream

An elaborate surprise proposal moves from street to stage—where dreams and reality blur at a Greenwich Village theater

The moments after Jeff proposed to Chelsea- rain still falling, engagement ring catching the light

I was nervous for this one. Proposals always have a unique kind of pressure. I would argue (perhaps controversially) it’s the hardest assignment for a wedding photographer. A lot of hurry-up-and-wait-energy and then everything unfolds super quickly. Jeff messaged me the Friday before Thanksgiving. He and his girlfriend Chelsea would be in New York to visit family for the holiday and he decided this would be the perfect time to propose. It was a bit last minute for everyone, but he had an epic vision. He’d picked a popular location in the West Village around the corner from where Chelsea’s parents live. He worked everything out with the theater to use their lobby, booked a guitarist to pretend to be a street musician to reel Chelsea in with her favorite song and he booked a table in the bar for after where her friends and family would further surprise her with a champagne toast.

I started having stress dreams about it two nights before. Twenty years in and this job still exhilarates me. I was worried I wouldn’t be in the right place, or that I would somehow give away the surprise or that I’d be set up to shoot outside and then have to quickly head inside and I’d miss Chelsea’s reaction.

Outside Cherry Lane Theater on a rainy night just before Thanksgiving

Jeff, perhaps more understandably, was nervous too. He and Chelsea live in Texas, but he planned this whole thing the weekend before from a boys’ trip in London. He flew back on the day of the proposal, rushed to pick up the ring from the jeweler, all while fielding concerned texts from Chelsea about why she couldn’t see his location and plotting with her friend on how to get her into place and getting her family and friends to the bar.

Chelsea and Jeff outside Cherry Lane Theater moments after the proposal - still in the dream

Of all the surprises lined up that night, the rain was probably the biggest one. It was the kind of dark, wet fall evening where you simply want to stay warm and cozy and safely inside. Yet I had to admit, the city felt a-buzz with holiday energy. I could feel a crackle in the air. And in so many ways, the rain turned into the hero of the story. What was supposed to happen outside moved inside. And Cherry Lane Theater graciously offered us something no one expected: the actual stage. Not a lobby or back room—the stage itself, in one of Greenwich Village's oldest continuously running Off-Broadway theaters.

Jess proposes to Chelsea on stage at Cherry Lane Theater.

I arrived a full thirty minutes early. I tested my flash I can’t even tell you how many times. Jeff kept running in and out to check on one thing or another. The guitarist was set up outside the door. Random strangers kept popping in causing false alarms and psyching me out. Text updates were alerting us to Chelsea’s impending arrival. I was waiting just behind a massive set of red doors anxiously checking my exposures. Jeff was positioned halfway down the theater steps anxiously checking his phone.

Just engaged on the stage where a century of stories have unfolded

First I heard the music, then I heard the voices. I heard a woman excitedly asking the guitarist how he knew this song. She was saying it’s her song with her boyfriend, but no one’s really heard of it. She said she wants it to be her wedding song but while the melody is beautiful the lyrics are a little melancholy. She asked if she could record him. The word Phosphorescent floated into my memory. I felt a smile at play on my lips. Jeff too had told me it was an obscure song, but somehow it didn’t surprise me that it lived in my heart too. This was “A song for Zula” by Phosphorescent and it had lured Chelsea into the drama of the moment exactly as Jeff had envisioned.

Pure joy - Chelsea shows off her ring outside the theater.

Then everything felt like it sped up again as the guitarist opened the doors and Chelsea burst into the theater.

Chelsea said afterward that she felt like she blacked out once she got inside that theater.  Mysterious things happen with camera gear sometimes that I will never be able to explain. What I will shyly tell you is that against all odds, despite having tested it profusely, my flash blacked out as well. All I know for sure is that the energy travels through my subject and then through me and then through the cameras, and that energy has its own signature. Despite having tested this flash countless times in the moments leading up to this, at the crucial moment, it had a mind of its own. Please don’t miss understand me. The photos came out beautifully. Just not in the way I planned. The surprise of the moment was too massive, too overpowering. The exposure blacked out too, but just for a moment. Chelsea’s shocked smile frozen in time, but the beautiful red door I had planned as a backdrop, totally disappeared into the darkness.

Chelsea's friends and family emerging from the theater bar after having a champagne toast inside.

As Jeff led Chelsea onto the stage, I felt hyper aware of the fact that I was the only other presence in the room. Chelsea had told Jeff she didn’t want an audience for her proposal, and I could tell that even just having me there made herself conscious. She was well and truly surprised. She kept piecing together tidbits of information, trying to reorder her present reality into something that made sense. ‘So that’s why your location was turned’ ‘What time did you get in’ ‘Is that how he knew our song?’ ‘I feel like I’m dreaming right now.’ The setting felt particularly surreal. Can you imagine stepping in from the rain, thinking your boyfriend is stuck in traffic and hours away and instead he's leading you onto a literal stage to propose? I imagine it felt like she stepped out of reality for a moment into the thin space between dream and reality.

Heading to Commerce Inn to celebrate - the dream continuing into the West Village night

She said yes. The ring, two sizes too big, was put on her finger. Misty rainy photos on the cobblestoned Commerce Street were taken. Champagne was had. Her family and friends poured outside for a group photo and then they all filed into Commerce Inn to keep going. I quietly, shakily packed up my gear. It was a quick little shoot, but what a jolt of love and joy that went through me. I called a friend to help me come down from the high of it all. I told her about the flash. I told her about how against all odds one of my batteries died too. I said ‘I’ll never understand why these proposals are so stressful.’ She replied, ‘yeah but would you do it again?’ ‘Of COURSE!’.