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Jessica and Christopher, Surprise Engagement Proposal | Boston Engagement Photographer

Updated: Sep 9


Man kneels proposing to woman in yellow dress by waterfront. City skyline in background, chain railing visible. Romantic moment at sunset.

Christopher & Jessica are one of my favorite couples — their love is so sweet and fun, they are so supportive of each other’s career, and you can just tell that they have each other’s back in the little moments and the big ones.


When Christopher reached out to me about capturing the proposal, it was an easy yes (followed by Jessica’s easy yes to his question)!


I’m so happy for these two and I can’t wait to watch your love grow for years and years to come!


Keep scrolling to see some of my favorite photos from their engagement session at the East Boston Waterfront!



Christopher + Jessica | East Boston Waterfront | 06. 18. 2025


Man kneeling and proposing to woman in yellow dress by waterfront. Boston city skyline in background, creating a romantic, serene atmosphere.
Man proposes on one knee to woman in yellow dress by waterfront, Boston city skyline in background, chain fence, soft sunset light.
Man kneels proposing to woman in a yellow dress by the waterfront. City skyline and sunset in the background. Romantic and emotional moment.
A couple smiles at each other by the waterfront with a cityscape in the background. Black and white, emotional, serene setting.
Couple touching foreheads and smiling brightly by a sunlit waterfront. Woman's ring visible; warm, joyful mood. Background is slightly blurred.
A couple smiles by the waterfront at sunset, with city skyline and boats in the background. One wears a yellow dress, the other a blue shirt.
A couple embraces by the waterfront at sunset. The man wears a dark shirt, the woman a yellow dress. City skyline and boat in the background.
A couple embraces by a waterfront at sunset, smiling. The city skyline and boats are in the background, with warm golden light.
A hand holds a diamond ring by a waterfront, with blurred buildings in the background. Black and white image, creating a sentimental mood.
Couple in loving embrace at sunset by waterfront. Man in blue shirt, woman in yellow dress; calm, romantic setting with soft light.
A couple smiles by the water, with city buildings in the background. She wears a white dress and an engagement ring. Black and white photo.
A couple stands by a waterfront at sunset. She wears a yellow dress, resting her head on his shoulder, and they both smile warmly.
A couple holds hands walking by a sunlit waterfront. She wears a yellow dress, he a dark shirt. Both are smiling, evoking a joyful mood.

Boston couples: if you recently got engaged and are looking to capture this momentous occasion, fill out my contact form and let's chat! Click here to get started!

 
 
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Taylor Rossi Photography offers headshots, event photography, family photos, engagements, & intimate weddings in Boston, MA and beyond.

Taylor Rossi Photography is an LGBTQ+ and Woman-Owned business. All are welcome here!

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