Matthew and Deena
How we met
I met Deena around Fall in 2015 after I had moved back to Central Illinois. I actually found her on a dating app (which that shall not be named) and we started texting back and forth for a few weeks. I thought we had quite a bunch in common so I invited her out for wine one night. Apparently, Deena thought from my picture that I was “ultra handsome” and that hydration is important, so why not! Deena had a fear of talking too much but I tried to match up to her talkativeness which I thought was cute. I think I wooed her with my extensive knowledge of useless information because after that night, we were basically inseparable.
How he asked
After a year and a half of dating, we decided that we wanted to move in together when we moved into the city of Chicago from the west suburbs. At that point, I already knew that I wanted to be with her for the rest of my life. Deena had a hunch that I was going to propose to her this past Summer but she didn’t know when. I thought I’d catch her off guard if I did it the day we moved in together. I wasn’t entirely familiar with the area so I hired a local photographer, Yasmin from La Bella Portraits, to help me plan the perfect proposal and get some pictures of it so that we can hang them in our new home. So with Yasmin’s help, I decided to propose at Montrose Harbor with the Chicago skyline as the background to symbolize our new life together as an engaged couple in our new home.
The day arrived when I was going to propose, and I was getting nervous because the weather said it was going to rain that day. It was also the same day we arrived in town so I took her out to brunch after we had dropped off our things in our new apartment. After brunch, we made our way to the Montrose beach so that we can check it out and so that Yasmin can easily spot us as we’re walking. As we were just walking and talking from the beach, to the pier and harbor, my stomach was all up in knots from being nervous. As soon as I felt we were in a good spot in front of the skyline, I dropped down to one knee and asked Deena to marry me. At first she didn’t believe me, but then she said yes!
After the proposal, we had some more engagement pictures taken and I asked her if she expected me to propose today. She said she honestly had no clue that I was going to propose today because of our hectic schedule but she’s glad I did.