Brian’s Nighttime Commonwealth Ave Proposal to Kailen

There’s nothing quite as exhilarating as photographing a surprise Boston Commonwealth Ave Proposal

“I’m picking up the ring on Friday and would like to propose in Boston Comm Ave Mall the day afterwards. Can you photograph the moment for me?”

Yes. Yes. Yes.

So much yes.

I’ve photographed dozens of Boston marriage proposals, however, this is the first where the shoot was completely dependent on something wildly out of my control.

You see, Brian wanted to photograph between Clarendon and Dartmouth Ave on the Comm Ave mall. For non-Bostonians, you’ll know that it’s a street in the Back Bay that is stunningly gorgeous because of its lit up twinkly lights on trees, awesome dog watching, and charming brownstone apartments. Here’s the issue: neither one of us knew when the lights turned on. We knew they turned on after sundown, which was around 4:12 that evening.

I started scoping out the scene at 3:45pm. Around 3:50, the lights on the first three blocks (Arlington, Berkeley, and Clarendon) turned on. Awesome. Promising. At 4:05, all the other blocks (Exeter, Fairfield, Gloucester, and Hereford) turned on…

EXCEPT for my block, Dartmouth.


I’m texting Brian. He and Kailen live on Marlborough St, only a couple streets away. He told her a lie that they would go out to hang out with his friends for a drink, and that’s why they were walking from their apartment through the Comm Ave Mall.

We continued waiting until 4:25pm.

Still not lights.


At this point, my assistant, Phoebe, and I were sitting on a bench, but I start standing, pacing, and muttering under my breath. “Trees, please turn on. Blue light is here and it’s perfect. Please turn on. Please please please.” Little squirrels in the trees stared at me as I talked to the branches that they perched on.


4:27 is now my new magic number, because the lights between this important block turned on and I internally rejoiced.

Brian and Kailen walk down the street, in beautiful wool coats. He knelt down on one knee, and Kailen was surprised with the most beautiful ring and of course, she said yes. 🙂

Congratulations you two. Brian, you were amazing. 🙂

See more Boston Commonwealth Ave Marriage Proposal Photography by Boston Proposal Photographer Nicole Chan

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