Connor & Kaitlin’s Seaport Proposal

Some stories feel especially full-circle, and Connor and Kaitlin’s is one of them.

Our story together actually started last spring, when Kaitlin reached out to book a graduation session for her and her boyfriend, Connor. Both were graduating from law school and wanted to celebrate with photos in the Boston Public Garden, dressed in their caps and gowns. From the moment I met them, I could tell how special their connection was. They’d been together all throughout college, and there was such an ease and sweetness between them—it was impossible not to think, these two are going to make it.

So when Connor reached out in early 2026 to ask if I would photograph his proposal to Kaitlin, I couldn’t have been more excited.

His cover story was a good one: he told Kaitlin they were headed to a family member’s retirement dinner in the Seaport District, which gave them the perfect excuse to get dressed up and take a spring stroll through Fan Pier Park beforehand.

This proposal came with one unique challenge—I’d already photographed them before, which meant Kaitlin would definitely recognize me if she spotted me. We had to get creative.

My secret weapon? My trusty 9-year-old assistant—my son.

Armed with his skateboard, he cruised around nearby while we waited. I showed him a photo from Connor and Kaitlin’s graduation session, turned my back toward the direction they’d be walking from, and told him to give me a signal with his eyes when he saw them coming. (Honestly, he crushed it.)

Then came the moment.

Connor dropped to one knee, and suddenly all the planning disappeared into pure emotion. The two of them were overwhelmed with joy, and my son and I were off to the side absolutely squealing over getting to witness it.

And then came the detail that made all of us tear up.

After Kaitlin said yes, Connor pointed out something incredibly meaningful in her ring—one of the side diamonds had been taken from her late mother’s ring.

Cue all the tears.

After giving them a moment to soak it all in, we spent the next part of the evening taking engagement portraits around the waterfront. My son proudly showed off some of his skateboarding skills along the way, and Connor and Kaitlin were kind enough to let him tag along as an honorary member of the photo team.

But Connor wasn’t done surprising her yet.

Waiting just nearby at Davio’s Northern Italian Steakhouse were all of their closest friends and family. They had been watching the tail end of our session through the restaurant’s grand glass windows—cheering, smiling, and raising glasses from inside. As we walked over, Connor led Kaitlin into a room filled with hugs, happy tears, and all of the people they love most.

What an incredible way to begin this next chapter.

It was such an honor to be chosen again—to go from documenting Connor and Kaitlin’s law school graduation to capturing the moment they got engaged feels incredibly special. As a photographer, being invited back into someone’s story is one of the greatest compliments there is—and I’m so grateful I got to witness another beautiful milestone in theirs.

Connor and Kaitlin—thank you for trusting me (and my little assistant) with such an unforgettable day. I can’t wait to see all that’s ahead for you both.