Two years, lots of Bruins games, and an adopted black cat later (we love you, Mia!), it was time for Derek to attempt the impossible: surprising Kathryn Quaglia.

After speaking with Vito & Melanie over FaceTime to receive their blessing, he began making preparations. The problem? His detail-oriented future fiancée would notice every single time he would turn off his location. Nonetheless, after two trips to the jeweler, he had the ring.

(She definitely didn't search for, and find, the ring box a few days later.)

Coincidentally enough, it was Derek's responsibility to plan their two-year anniversary date. Taking the reigns, he laid out the plan: a brief drink at The Anchor for nostalgia's sake, followed by an appearance at a private event at Pier 6, and capped off with dinner for two at Dovetail. It was a Charlestown extravaganza!

But on their two-year anniversary, Kathryn would surely be suspicious of this agenda. Leaving some flexibility in the timing and even enlisting Dave's help for the private party's dress code, Derek gave it his best shot to maintain his cover.

When Saturday, April 1, 2023 finally arrived, these two lovebirds were both sweating it out. Kathryn had her suspicions, especially after seeing a TUMS wrapper in the trash can and concluding that Derek was a nervous wreck, too.

They Ubered to The Anchor for the nostalgic drink, only to find that it was closed.

Now or never, right? "Let's just take a selfie over here," Derek pivoted.

As Kathryn tried to get into position, Derek followed up with a correction. "We're not takin' a selfie, Bucko."

She had known it was coming, and now she knew it was happening.

"RIGHT NOW?"

Those were the two words that slipped out amidst Kathryn's rush of emotion.

From a knee, Derek began with three words.

"Kathryn Michelle Quaglia..."

She did, in fact, say yes!

​

A little while later, we were on our way to Pier 6 for the real event—the surprise engagement party with lots of family and friends, waiting to celebrate the newly engaged couple.