Jesslyn + Bobby | Roarin’ 20s Lawn Party: Surprise Proposal

About three months ago, I was asked to ‘save the date’ for a surprise proposal at The Roarin’ 20s Lawn Party at Castle Hill on the Crane Estate in Ipswich, MA. This request was particularly near and dear to my heart — not only because I love love and was given the chance to photograph such an amazing moment between two people, but also because it’s two people I love dearly and am lucky to call my friends.

When Bobby shared his plan to propose to Jesslyn, I knew it was going to be exactly what she always wanted: a big surprise and surrounded by friends to celebrate this amazing milestone with them. I could barely contain my excitement then, but I am even more excited that it finally happened and I get to share this love-filled post now!

So, fast-forward to July 31st: We arrived around 3:30pm and spent a few hours enjoying the 20s music and outfits while Bobby scoped out the perfect scene to surprise his lady. Once I got the cue that it was time to make a move, we headed up the hill to ‘take a big group photo with the castle in the background’ before the sun went down. Little did Jesslyn know that the group photo would turn into one of the most memorable moments of her life.

Spoiler alert: she said YES! And now, before I get too sappy, here’s some of my favorites. Congrats and best wishes to Bobby and Jesslyn as they start this next chapter of their life-long journey together:

BobbyJesslyn_SurpriseProposalPhotography01 BobbyJesslyn_SurpriseProposalPhotography02 BobbyJesslyn_SurpriseProposalPhotography03 BobbyJesslyn_SurpriseProposalPhotography04 BobbyJesslyn_SurpriseProposalPhotography05 BobbyJesslyn_SurpriseProposalPhotography06 BobbyJesslyn_SurpriseProposalPhotography07

BobbyJesslyn_SurpriseProposalPhotography08 BobbyJesslyn_SurpriseProposalPhotography09 BobbyJesslyn_SurpriseProposalPhotography10 BobbyJesslyn_SurpriseProposalPhotography11 BobbyJesslyn_SurpriseProposalPhotography12 BobbyJesslyn_SurpriseProposalPhotography13 BobbyJesslyn_SurpriseProposalPhotography14 BobbyJesslyn_SurpriseProposalPhotography15 BobbyJesslyn_SurpriseProposalPhotography16 BobbyJesslyn_SurpriseProposalPhotography17 BobbyJesslyn_SurpriseProposalPhotography18 BobbyJesslyn_SurpriseProposalPhotography19 BobbyJesslyn_SurpriseProposalPhotography20 BobbyJesslyn_SurpriseProposalPhotography21 BobbyJesslyn_SurpriseProposalPhotography22 BobbyJesslyn_SurpriseProposalPhotography23 BobbyJesslyn_SurpriseProposalPhotography24 BobbyJesslyn_SurpriseProposalPhotography25 BobbyJesslyn_SurpriseProposalPhotography26 BobbyJesslyn_SurpriseProposalPhotography27 BobbyJesslyn_SurpriseProposalPhotography28

6 thoughts on “Jesslyn + Bobby | Roarin’ 20s Lawn Party: Surprise Proposal”

  1. Susan Hunt
     ·  Reply

    This was a perfect post, it truly reflects the emotions and happiness throughout that day. Overwhelmingly beautiful words & captured moments! Great job Jenna!

  2. Jamaris
     ·  Reply

    Entirely love this????

  3. Kathleen Hazen
     ·  Reply

    Beautiful moment beautiful pictures. Congratulations!!!!

  4. Susan Koning
     ·  Reply

    Omg. this is awesome. I am Bobby’s Mom…. I would love to get a copy of these if i could…Thank you so much !

    • Jenna Burpee
       ·  Reply

      Hi Susan – sorry this took so long to respond! If you would like copies, please email me directly: and I will take care of you! Congratulations 🙂

  5. Beverly
     ·  Reply

    Such a beautiful romantic love story. May you both be blessed with a long loving life as this fairy tale story! Bobby you did a great job. Now as you start a new life together with all your loving friends & family enjoy every loving moment! ????CONGRATS ????

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