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Deana & Massimo

Saturday, August 2, 2025 • Windsor, ON, Canada

Deana & Massimo

Saturday, August 2, 2025 • Windsor, ON, Canada

11 Years Ago, It Started With A Wedding

Picture it, a warm summer evening in July of 2014. Massimo arrives at the Ciociaro Club to bartend a wedding with over 700 attendees not knowing he was about to meet with the girl who would change the course his life forever. Deana, after day of excitement and celebration arrived at the Ciociaro Club for her brother's wedding reception, it was that night where she would lock eyes with her real life "Leonardo Di Caprio." Unfortunately, due to Massimo not picking up on the right signals, he missed out on his chance with Deana which would lead to 8 years of chasing for a second chance.


In August 2022, after back and forth conversations and missed connections on Hinge and Bumble, Massimo decided to do something he had never done, he slid into the DM's (direct message) on Instagram. Finally he would get his chance to talk Deana. They decided that drinks at The Bourbon Tap and Grill was the perfect way to take the first step toward forever. Who would have thought that after 8 years, these two hopeless romantics would spend the next 7 hours talking about everything and anything until the bar closed.


So began the next 2.5 years filled with wine tours, countless adventures (Niagara, Las Vegas, Chicago, Montreal, Toronto, just to name a few.), globe trotting culinary adventures without leaving the kitchen, and dozens of unfinished tv series and movies.


On the 16th of March 2024, Massimo decided to take the next step toward forever. He got down on one knee on one of the windiest days of 2024 at Viewpointe Winey to propose to his Deana.

First Photo Together

December 04, 2022

First Photo Together
First public appearance

December 15, 2023

First public appearance
First sporting event

January 24, 2023

First sporting event
Frist road trip

February 20, 2023

Frist road trip
First birthday together

March 25, 2023

First birthday together
First wedding attended together

July 02, 2023

First wedding attended together
First wine tour

July 21, 2023

First wine tour
Memory

August 16, 2023

Memory

September 16, 2023

Memory

September 23, 2023

Memory

September 30, 2023

Memory

December 02, 2023

The day she said YESSS!!

March 16, 2024

The day she said YESSS!!