Waterfront Engagement Photos in Downtown Annapolis | Caroline & Dan

February 27, 2018

Caroline and Dan met us on one of the warmest days for what they thought would be winter waterfront engagement photos in downtown Annapolis. We walked around the State House, down Maryland Avenue and then drove down to the City dock in Annapolis for sunset engagement photos.  Caroline’s plaid scarf and Dan’s navy half-zip were perfect outfits for a more casual look!  These two had so much chemistry together and it makes photos easy when two people have so much fun being around each other <3

aroline and Dan met in the small town of Parkton, MD at Hereford High School.

Caroline was a freshman and had a crush on the popular, attractive, athletic, funny, senior boy- Dan. Dan definitely noticed the beautiful, dark haired freshman girl as their paths would cross at some of same parties since Dan’s younger brother and Caroline were same age and had some of the same group of friends. Dan and Caroline both felt that there was a connection from their early ages, but as many high school crushes would have it, the timing just wasn’t right…. yet!

Fast forward through “life”. It was not until many years later, one summer night after a Baltimore Orioles baseball game that timing was finally on their side. They ran into each other and instantly reconnected.

and Caroline reminisced about the past and the memories of each other. Caroline told him about her senior boy crush and he told her how he has always loved her. Caroline said when she looks back on it, she doesn’t know if they had dated back in high school, if they would be where they are today. She said “I may not have seen him in the light that I do now.”

After a few years of dating and building a life together with their friends and families, Dan decided to propose to Caroline at her family’s restaurant by the pond- he even included their dog, Harper! Dan chose this particular spot since it held a special place in Caroline’s heart with lots of memories of her and her Grandmother growing up.

Caroline and Dan’s paths may have traveled in different directions for a little while, but it is clear that everything happens for a reason when it comes to these two!

“Dan is most attractive, caring, and loveable man I have ever been with” – Caroline

“I can’t begin to explain how lucky I am to have found someone as special as Caroline. I love her more everyday” – Dan

Looking forward to their wedding with Elizabeth Bailey Weddings at their private family farm and restaurant later this fall in Upperco, Maryland, Friendly Farm Restaurant (Hopefully soon to be wedding venue!!!!)

Annapolis engagement photomaryland state house engagement photomaryland state house engagement photolace navy dress engagement outfitlace navy dress engagement outfitstate house engagement photolace navy dress engagement outfitstate house engagement photosunset engagement photoannapolis engagement photoannapolis engagement photoannapolis engagement photoannapolis engagement photostate house engagement photostate house engagement photoannapolis engagement photoannapolis engagement photomaryland avenue engagementmaryland avenue engagementengagement ring on a dockcity dock engagement sessioncity dock engagement photoswaterfront dock engagement photosengagement photo locations annapoliscity dock engagementdock street engagement picturesannapolis engagement picturesengagement pictures in annapoliswinter engagementplaid scarf engagement outfitscasual engagement outfitengagement photos on a pierengagement photos by the waterchesapeake bay engagement pictureschesapeake bay engagement pictureschesapeake bay engagement photoschesapeake bay engagement pictures