Diane and Charlie

Image 6 of Diane and Charlie

How We Met

In December 2015, my coworker brought his roommate, Charlie, to our company holiday party in Philadelphia. We clicked pretty immediately, realizing we liked the same music, food, activities, & hobbies – but I wasn’t interested in having a relationship. Throughout that first year of friendship, we hiked together, went to concerts together, ate out together, drove to the beach together, ate many hot wings together, and more.

Image 1 of Diane and Charlie

Image 2 of Diane and Charlie

Our friendship snowballed and by November 2016, we found a cheap all-inclusive Punta Cana vacation and decided to go together (“as friends”, yeah right!). By the end of our first vacation, we were officially boyfriend & girlfriend. One month into the relationship – one year after we first met – the “L” word was shared. Since then, we have enjoyed countless spontaneous trips, restaurants, concerts, hikes, rock climbs, kayak adventures, recipes, and many, many drives to the beach. He was always more than my boyfriend, he was my best friend first and foremost.

Image 3 of Diane and Charlie

Image 4 of Diane and Charlie

Image 5 of Diane and Charlie

How They Asked

We decided to save up and splurge on a vacation to Greece for May 2020! Leading into May, and unbeknownst to me, Charlie was spending countless hours while I was traveling for work searching and customizing a ring. We booked a spot on the cliffs of Santorini with a hot tub overlooking the sunset on the Aegean- this is where Charlie was going to propose.

Image 7 of Diane and Charlie

I promise, I had NO idea (mostly because “I’ll lose the ring traveling internationally” made perfect sense to me – he lost his glasses floating in the ocean last week!) Due to COVID-19, Charlie’s plans were altered. Instead, he drove me down to Anna Marie Island on a random Tuesday night, walked me to the edge of the island during sunset, said he wanted to spend the rest of his life with me, and got down on one knee. I stared back blankly, out of pure elated SHOCK, but YES, YES, YES!

Image 8 of Diane and Charlie

He told me later, he didn’t want to wait another year for us to reschedule our Greece trip to make me his fiance (my heart!). He thinks a proposal at sunset on a random Tuesday night was his backup plan, but I think it’s the most “Diane & Charlie” proposal ever! We both love spontaneity, the beach, and making the most out of every day – even random Tuesdays in the middle of a workweek.

Image 9 of Diane and Charlie

Due to the pandemic, we didn’t have a photographer to capture the moment, my nails can’t be properly painted, we aren’t able to celebrate with family & friends, but – it was absolutely PERFECT. I get to spend the rest of my life with my very best friend. (And of course, we ate hot wings the next day together to really celebrate).

Image 10 of Diane and Charlie

Special Thanks

James Allen
 | Ring