Kerry and Oscar
How We Met
We met at a mutual friend’s housewarming party on their infamous “comfy couch”. We had shared this mutual friend for years and had even gone to the same college and lived a block away from each other but never met before this moment.
We ended up sharing an Uber ride home since we lived in the same neighborhood. The next morning Oscar accidentally met my mother while she was helping me move out of my current apartment (in Hoboken, NJ) and back into NYC. My Mom mistakenly assumed Oscar was hired to help me move out and poor Oscar politely carried all of my furniture and clothes in and out of the apartment for hours on end. Eventually, after feeling awful that this guy I just met was helping me move out all of my stuff – he said he needed to head out. As my Mom tried to offer him some cash, I was incredibly embarrassed. But Oscar was a gentleman, asked for my phone number and I expected to never hear from him.
Hours later, he texted me something along the lines of “It sounds like you had a tough day” and asked me out for dinner. We had our first date at Onieal’s in Hoboken. A week later, I moved back to NYC and we began this “across the river” relationship. Each of us carting our stuff back and forth on the PATH train, subway and ferry until 1.5 years later when Oscar started looking for apartments in Jersey City, NJ. He involved me in the whole apartment hunting process and I knew wherever he’d land would eventually be our home together. From that point on, Oscar asked me to move in and I left my NYC home (for ~6+ years) for our new home together in Hamilton Park, Jersey City, NJ.
How They Asked
After 2.5 years of being together, Oscar decided it was time to start the proposal “process”. He started thinking of the perfect, intimate, most meaningful way to propose. He already knew the ring I wanted after a fun ring shopping experience. And, he knew I wanted my siblings and his brother involved and that I wanted to be surprised. Somehow he came up with this idea to get a painting of us made. Oscar went on Upwork looking for local artists who would be able to paint a photo of us together, with him proposing in it. He picked particular outfits we’d be on that day that he knew we always had on hand. Once that part was taken care of, he started to rope in the siblings.
He started off with getting my sister to make up an excuse to come to Jersey City at 4 PM on a Sunday (she said her boyfriend’s friends would be around for Sunday Funday football). I somehow fell for that, despite the fact that my sister rarely visits the area. She then had my younger brother said he also wanted to join in on the fun. That was likely the only major thing that could’ve thrown me off, as my brother is nearly 9 years younger, he never wants to hang with us. From there, she asked Oscar to “plan a fun day” for us – little did I know Oscar had already planned out the whole day on an extensive Google doc. And about a 1/2 hour before we were supposed to paint, Oscar’s brother and his fiance texted us asking if they could join. This wasn’t out of the ordinary as we hang out with them on the fly regularly.
Oscar had hired a local Paint and Sip company to come to our local park (Hamilton Park, Jersey City) to have us all paint fall pumpkins together. I was completely fooled by this idea and did not do my hair or makeup or really wear a particularly lovely outfit. I had just gotten a facial done and was totally unprepared.
After the painting of the pumpkins commenced, the host of the Paint and Sip said he’d like to pick a winner for “best pumpkin”. I thought the prize was a coupon for it to be framed. My little brother proceeded to hold up this huge piece of a cardboard easel (which was the determined prize) and he opened it – to my surprise it was Oscar proposing to me in the painting.
Lo and behold, I was completely shocked. Please enjoy all of the videos/pictures that occurred afterward.
99% of Oscar’s plan went well, except for the fact that I ended up drying clean the red dress in the painting the DAY before my engagement (as I had no idea I’d need it so soon). Poor Oscar did not realize this until right before we left for the park but played it off well.
We spent the rest of the evening getting dinner at a local restaurant on the park, my sister and future sister-in-law painted my nails and helped do my makeup and we made enough Facetime phone calls to kill a fully charged phone battery.