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Candid Moments: A Fall Engagement Session in Downtown Boston

An engaged couple embracing while posing on Acorn Street in Boston

This trip down to Boston in late September to meet up with Ivy and Tyler for the first time turned out to be quite a special one! We had been chatting back and forth with them for several months after they booked us for their November 2024 wedding at The Lace Factory in Connectcut. Quite honestly, before even seeing them walking towards us from afar in Boston Common it felt like we were all old friends. And you always know it's going to be a good shoot right away when you're starting out with those vibes!

With quite an ambitious itinerary planned for the afternoon in order to pack in multiple locations around the city , we decided to head over to the infamous Acorn Street in Beacon Hill. This being the first time any of us had been there, we certainly weren't expecting the incredible 'Instagram vs. Reality' situation going on there! Maybe because it was a nice day, or maybe just because it was a Saturday, there were so many people taking photos and admiring the street that it became nearly impossible to get many great shots without a ton of photobombing from every direction. We quickly moved on and found a side alley nearby that was just as quaint, and more importantly, empty! Tyler and Ivy quickly took this to their advantage and immediately feel right into being their adorable selves, cuddling up and skipping around the block!

As a super fun bonus and a sign that there were plenty of good vibes in the air, a random stranger walking down the street asked if we wanted a free apple cider donut! Uhhh, yes please! And of course these two were just ridiculously cute about the whole thing as they cheersed their pieces and then offered us a bite!

A couple holding out pieces of donut to offer towards the camera

Did we mention this alleyway (whose location we will keep a secret so it doesn't get overrun!) also has a super cool doorway to take pics in front of!? Ivy and Tyler immediately found their spot and started hamming it up for our cameras before slowing down for a moment to get a bit more romatic with their posing.

Close up image of a guy and girl looking at each other with a dark background.
Close up image of a guy and girl embracing as the girl looks directly into the camera and the guy looks down.

Our next stop was Boston Public Garden, but when you're already giggly and having a blast it's hard not to stop for a few shots in front of a giant red neon sign that reads 'FRESH MEATS,' because come on, we're still all little kids at heart laughing at doodoo!

A couple looking at each other and smiling in front of deli with neon sign reading Fresh Meats

A couple kissing in front of deli with neon sign reading Fresh Meats

The Public Garden and Common is such a wonderful location to be smack dab in the middle of a big city like Boston. To be on a busy city street one moment, and then suddenly surrounded by green space in every direction, is a welcome respite from the hustle and bustle. As an added bonus, the stark contrast of nature against massive buildings on the horizon makes for some wonderful images. And of course these two and their nonstop candid moments brought their own little magic to the entire scene!

A very happy couple hugging and smiling wide in Boston Public Garden

A man and woman laughing in front of a pond in Boston Common

It's always incredible to see how effortlessly some couples openly express their love for one another, and we definitely feel like you can tell that Ivy and Tyler are one of those pairs just by glimpsing the moments captured in these photos. A big part of our style is trying to not pose couples too much, instead having them move into a space and letting things happen organically, which creates a much more candid vibe to the images. Sometimes we'll give a prompt to get things going, and sometimes the couple just dissapears into their own little romantic world and forgets we're even these two!

A blurry black and white image of a man spinning a woman around in his arms

After having WAY too much fun and remembering the clock was ticking on daylight, it was time for an outfit change! Thank goodness for the impressively clean and spacious public restroom trailers in the garden, as they provided a perfect stop for Ivy and Tyler to change into slightly more formal attire before we strolled over to Chinatown.

An engaged couple embracing in front of an Asian gate in Chinatown in Boston

Of course now that they were dressed up a bit, Ivy and Tyler began to take the session a little more seriously and focused on making sure things were a tad more formal.

Just kidding. They started chasing pigeons around the streets and played on a playground.

A couple chasing after pigeons on a street in Boston

A man and woman playing on a children's playground in downtown Boston

Our final stop before we ran out of light was the South Station, where we quickly discovered our idea of capturing some epic train station photos wasn't going to happen because the interior was small and terribly lit- not the Grand Central Station look we had envisioned. That being said, we still took the time to snap a few photos before finding a great spot outside of the station with the beautiful entryway in the background.

A couple facing one another and smiling inside the South Station in Boston

As the sun went down we wrapped up the photos and walked back towards Boston Common to drop off our equipment. To cap off an already fantastic afternoon, these two wonderful humans offered to take us out for dinner, which we happily accepted. While we had packed so many adventures into just a few hours, there was still so much for us all to catch up on!

A man and woman kissing underneath paper lanterns in Chinatown in Boston.

Interested in joining us for your own engagement session?! We include them free of charge with both our 9 hour and 12 hour wedding photography packages! Not ready to book for your wedding quite yet? A la carte sessions are $500 and include approximately two hours of shooting, as well as multiple locations as time allows. Most couples also usually bring a change of outfits as well, but that's totally up to you! Reach out to us today through our Contact page and schedule your session!


Greetings, Earthling!

We're Bonnie and Jon, otherwise known as #TeamBonJon, and we're here to document your wedding day, not dictate it. 

We are a wife-husband videography and photography team based in southern Maine, capturing really cool, dope weddings and elopements across all of New England. 

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