Ah, the holiday season! A time for glittering Christmas lights, mugfuls of cocoa, Mariah Carey belting out on repeat, and a peculiar spike in four little words: “Will you marry me?” If you’ve noticed your social media becoming an engagement ring showcase between Thanksgiving and New Year’s, you’re not alone. This time of year isn’t just for mistletoe kisses and pine-scented candle obsessions—it’s also engagement season! Let’s dive into why so many rings are slipped onto the fingers of unsuspecting fiancés during this sparkling time. And don’t I have two perfect stories to exemplify this festive phenomenon?
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The Holiday Proposal Magic: Why So Many Say “Yes” This Time of Year
You could say the holiday ambiance practically demands romance. Here are a few reasons for the engagement season to snowball between Thanksgiving and Christmas:
- Family Ties
The holidays often bring us closer to family—and what better time to pop the question than when everyone is already in town, gathered in one place? Whether your family’s traditions lean toward cozy PJs and cinnamon rolls on Christmas morning or a more sophisticated sit-down dinner, the vibe of loved ones gathering feels significant. Plus, how easy is it to orchestrate a “spontaneous” celebratory champagne toast when everyone’s already around? - Decked-Out Backdrops
From glowing Christmas markets to towering, ornament-clad trees, the visual aesthetic of the season is top-notch. Add a dusting of snow (for those not living in California, where snow is as mythical as a unicorn), and voilà, you’ve got a scene straight out of a Hallmark movie. With such dreamy settings, a holiday proposal will feel like a fairytale moment—complete with twinkly stars and maybe even reindeer in the background (or a really well-placed Santa on the sidewalk). - Holiday Cheer = Yes Energy
Call it good timing, but it’s hard to say no when everyone is brimming with holiday joy. There’s something about December that makes life feel whimsical and magical. The warm fuzzies, the music, the lights—it’s like the whole world conspires to turn up the romance factor. Proposing during such an optimistic time is like having a morale-boosting cosmic sidekick saying, “Just do it!” - Travel Opportunities
The holiday season often ushers couples to bucket-list locations for mini getaways. Whether it’s New York City at Christmastime (more on that soon!), a charming European Christmas market tour, or just visiting a cozy hometown filled with nostalgia, a change in scenery enhances the magic. It’s almost easier to propose when you’re somewhere special. Of course, this also opens the door for some hilarious and picturesque proposal stories…
Speaking of memorable proposals during this engagement season, let me share two tales of true holiday magic: I recently worked with two clients—both named David (yes, really)—who entrusted me to photograph their surprise engagements in New York City this past December. As both their photographer and witness to these joyful moments, I can confirm that nothing beats a New York proposal during the holidays (well, maybe an anniversary shoot as I did for this Indiana couple visiting NYC for Christmas).
Double the Davids: A Tale of Two Proposals in the Big Apple
Two men. Same city. Same engagement season. Same reason. Same name. But two very different proposals. Here’s how each David pulled off their surprise winter wonderland moment.
First David: The “Fake Photo Shoot” Mastermind
First David (we’ll call him David-1 for clarity’s sake) was all about the experience. He likes to make memories feel special and unique wherever he goes—so, naturally, his proposal plan involved an intricate “fake photoshoot.” Isn’t that the hallmark of a good proposal? Layers of intrigue? He wanted to suggest to his girlfriend that they’d do a fun couple’s studio photo session as a date idea. His reasoning? They’d have a bit of creative bonding time, dress to impress, and snap some professional keepsakes. After all, what screams romance more than a well-documented date?
The day arrived, and true to David-1’s plan, both he and his girlfriend turned up dressed like stars on the set of a Vogue cover. Her dress was a stunning seasonal red that shimmered like those Santas in appropriately bougie department stores. His look? Matching elegance with a red-accented vest and sneakers sharp enough to make you double-take.
At just the right moment during the shoot, I directed her to turn and gaze fixedly out a large window as sunlight poured through like golden glitter. Meanwhile, David-1 fished the ring out of hiding—a confidence only someone madly in love could pull off without breaking into nervous giggles. “Turn toward the camera,” I casually requested.
She turned. And there he was.
Kneeling. Ring in hand. Eyes misty. And TOTAL silence on her part before she realized what was happening. (Spoiler: She said yes. Big yes.)
The only catch? His family, who should have burst into the studio with holiday cheer immediately after the big moment, hit a classic NYC traffic snarl and missed the timing. Instead, they joined via video chat and cheered virtually. No matter—David-1 and his brand-new fiancé couldn’t have cared less.
We continued the shoot, now capturing portraits of a newly engaged couple. And let me tell you, these two were stylish. Her red dress and his matching vest and sneakers screamed festive chic. They looked like they belonged in a fashion magazine, so I channeled my inner Annie Leibovitz and posed them accordingly, taking full advantage of the gorgeous sunset streaming through the windows.
Second David: When a Rockette Show Leads to a Rock
Now, we move on to our second David—David-2, who flew all the way in from sunny San Diego with his girlfriend. He is determined to use NYC’s holiday magic for his engagement season proposal. Being a West Coast couple, they’d packed in all the classic seasonal NYC activities, including seeing the Rockefeller tree and, of course, catching the famed Radio City Rockettes. After the Rockettes dazzled their way through kicklines and candy canes, my job began—photographing him proposing in the Big Apple in true holiday style.
The original plan? Some glamorous “paparazzi-style” shots as they strolled back toward their hotel after the show. I’d casually hide across the street, camera in hand, getting candids. However, the best-laid plans of mice and men (and proposal photographers) sometimes go awry. Unfamiliar with the city streets, they accidentally turned down the wrong street, leaving me stationed in the cold, checking my texts like someone waiting for a blind date.
Once I realized they weren’t looping back, I sprinted (and dodged several steaming pretzel carts) straight to their hotel, The Lotte New York Palace. The Rockefeller tree’s overwhelming crowds led us to a beautifully lit, stoic holiday tree just outside the hotel. Classy and private. David-2 got down on one knee, his girlfriend’s joyful shout tearing through the winter air: “YES!!!”. I’m not exaggerating when I say she was over the moon. She literally shouted her excitement to the entire hotel courtyard.
Cue laughter, champagne, and… an entirely unplanned subplot. Marie was so thrilled, she kept spontaneously shouting inside the hotel, “I’M GETTING MARRIED!” Lo and behold, another woman overheard and yelled back, “SO AM I!!!” Two women sharing a moment of pure, unadulterated excitement like soulmates bonding over the happiest coincidence imaginable. Naturally, I snapped a picture of the impromptu holiday sisterhood. Is this a holiday rom-com, or what? Telling you, engagement season!
Between poses under the hotel tree, moments warming hands by the lobby’s heating vents, and FaceTiming their families mid-shoot (at FULL volume, obviously), their excitement lit up the freezing evening. To finish, we circled back to Rockefeller’s iconic Christmas tree for a few last shots. Overhyped? Maybe for tourists. But for two people reeling from a freshly minted engagement, it was the perfect way to end the night.
Holiday Proposals: Pure Joy in a Bow-Wrapped World
This might sound cliché, but being part of these two Davids’ proposals reminded me why so many betrothals happen during this engagement season. The holidays feel monumental, with all the lights, grandeur, and family-orientated vibes lending themselves to big life moments. Some proposals, like David-1’s polished rehearsal-backed photo shoot, have all the quiet magic of intimate planning. Others, like David-2’s joyful sprint through midtown right into a glowing hotel courtyard, feel totally spontaneous, wild, and larger than life.
For both, the heartfelt “yes” and future planning that comes after was made even more special by the holiday cheer surrounding them. How could it not be?
As both Davids and their fiancées bask in the holiday cheer and the magic of their unforgettable proposals, they’ll have countless moments to cherish forever—and what better way to preserve those memories than with custom-made photobooks, perfect for reliving their love story for years to come.
And that’s a wrap on my engagement season chronicles! What do you think? Would you say yes this season, or are you keeping your plans for the OTT heat of Valentine’s Day, another engagement season contestant? Either way, love wins. Every time.
To anyone dreaming of saying (or hearing) those big words this season, soak up the wonder—and don’t be afraid to yell your joy across a festive public square. Who knows? Your future could be a mistletoe away. Marry Christmas, folks! 🎄🎅🏻☃️❆🎀🔔
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