Ali and Dan’s Downtown Boston Engagement Session

Brittny Drye Founder + Editor-in-Chief of Love Inc. Magazine | On-Air Wedding Expert | LGBTQ+ Inclusivity in the Wedding Industry

Makayla Jade Photography captured so many sweet moments in this downtown Boston engagement shoot. College sweethearts Ali and Dan took pictures through Beacon Hill and Back Bay, making sure to stop at the Charles River Esplanade where Dan proposed. I just love the way that Dan holds Ali's face tenderly as he kisses her, the loving gaze that they have for each other, how Ali fits perfectly in his arms — such romance in this shoot, you guys!

The Love Story

They met in college at the University of Michigan (go Wolverines!) during a party at Dan's fraternity. “Even though we were both under the influence of some college fun, we instantly had a connection and quickly became best friends,” says Dan. Their friendship grew through Greek life during the school year until one particularly eventful spring break in Cancun. After that, they never left each other's side. “Our best friend's brother picked us up at the airport with a sign that read ‘Mr. and Mrs. Hassing' as a joke, who would have thought it would become true five years later?!” laughs Ali.

The Proposal

Because they had designed Ali's ring together, she knew a certain question was going to be asked soon. The night before, Dan started a fake fight to throw Ali off … and it worked! The next morning, Ali went to meet up with friends for brunch and, for the first time in weeks, she hadn't done her hair or makeup, and didn't care what she looked like because she didn't think dan was going to propose. “Of course, this is when it all happened!” laughs Ali.

When Ali arrived at brunch, the surprises started pouring in. Unbeknownst to Ali, her best friend had flown in, and after many happy and excited tears on the street corner, she gave Ali a note from Dan directing her to have brunch with her friends and then go back to their apartment. This was the first of many notes sending her on a scavenger hunt throughout the city, reliving special moments of their relationship. The hunt ended at the Charles River Esplanade with Dan on one knee.



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