The first time we met was back in 2018 at a Sandy Neck Beach bonfire, when Maddy (our officiant!) tried to set us up. Only catch? David wasn’t single. So, that was that. A year later, we crossed paths again at Anejo in Hyannis. David was finally single… but this time, Alyssa and Maddy tried setting him up with Fiona (yes—our bridesmaid Fiona). Needless to say, that one didn’t stick either. Then came New Year’s Eve 2020 at Sissy K’s in Boston. Alyssa asked about David again, and Maddy wasted no time playing matchmaker. After midnight, David mustered up some liquid courage, walked over, and said, “Where did Maddy go?” One spilled drink, one selfie, and one New Year’s kiss later—we finally got it right.

After a little encouragement (and some help typing) from our groomsman Nate, David finally sent the text that started it all: “Haha okay so I’ve been wondering if you could deal with me at a bar in Boston… do you think you could do it again and let me take you out to dinner?” On January 7, 2020, we went on our first date — or as David liked to call it, his Cape Cod Tour Guide Experience. Never mind that Alyssa also grew up on the Cape. We spent the chilly winter day walking hand-in-hand to the Chatham Lighthouse, stopped by the Chatham Beach Shack (where David heroically saved a little injured bird), and wandered over to Gray’s Beach — not realizing it’s where Alyssa’s grandpa’s ashes are spread. It felt like a little sign from “Papa,” especially when a kiss happened at the end of the boardwalk. The date ended at Colombo’s, where David learned Alyssa is a very picky eater. She “accidentally” dropped her fork so she could pack up the rest to go (the sauce was way too chunky). Chunky sauce, a saved bird, a sentimental kiss — and somehow, that first date sealed the deal.

After a few more Cape Cod adventures and visits to each other’s colleges, David finally decided it was time to make things official. Alyssa introduced David to the movie To All the Boys I’ve Loved Before and casually mentioned how she’d always wanted a love letter like the ones in the movie. David, being the thoughtful guy he is, took the hint immediately. On March 1, 2020 he surprised her with roses, chocolate, and a handwritten love letter that ended with: “Will you accept this rose?” Of course, there was even a rose sticker — his special touch — since he knew Alyssa watched The Bachelor. And just like that, Alyssa said yes. The Netflix love story officially turned real-life romance.

On March 26, 2020, David and Alyssa exchanged another round of love letters — because apparently, they were already living their own rom-com. David’s letter ended with three little words that changed everything: “I love you.” He even added a whole extra page listing all the reasons why he loved Alyssa. Alyssa’s first reaction? Total panic. She was nervous but managed to say it back — even if she was a little taken a back. Sensing her nerves, David decided to give her some space and didn’t say it again right away. Fast forward to May 24, 2020 — they were at David’s apartment in Bridgewater, just enjoying the night, when Alyssa started feeling that magical moment again. She wanted to say it this time… but before she could, David looked at her and said “I love you” first. It was like he read her mind. Alyssa instantly lit up, said it back (for real this time!), and that was it — the nerves were gone, the love was real, and the rest is history.

After making it through a global pandemic, the end of college, two years of long distance, career changes, moving in together, and all the chaos that comes with your 20s — we can officially say we’ve been through a lot. Somewhere along the way, there were three “promise rings” But on 10/27/24 he finally gave her the real deal. After everything we’ve been through, we promised forever — for real this time.