It was senior year at SH and I had just went on a school trip to Tijuana Mexico with some fellow classmates, but also with some girls in Jill's class, 1 year below me. It was a great trip and we all bonded over our philanthropy. One of the girls on the trip did end up spilling some tea that perhaps there was a nice young girl in her grade named Jill who might or might not have her eye on me. I knew who Jill was and was automatically intrigued, I mean how could I not be, she's a stunner. So while sitting on the steps of the new gym shooting the shit with Rob Carlson, she happened to walk by. We spoke briefly and realized we might be at the same party later that night. We did end up crossing paths that night and we danced and had a blast. On our ride home (from a friends mom as we both didn't drive yet) it was relatively quiet, but then the driver got a phone call, and Jill went in for the kill! She kissed me and well, I haven't been able to get rid of her since! LOL
It all started in high school at SHCP. Jill was a junior at the time and had told one of her friends that she thought this 3 sport athlete name Cole was a total hottie. Fortunately for Jill, her friend had a big mouth and Cole caught wind from this gossip girl. She clearly was on his radar yet he still hadn’t found a chance to make his move. Later, before winter break, Jill found herself sitting on the steps of their high school gym until a mutual friend, Rob Carlson, or as we call him Hot Rob, walks up and sits next to her on the steps. He then asks Jill, “hey have you met my friend?". To Jill’s surprise, Cole walks through the doors and FINALLY introduces himself. Thanks Rob, you’re a real one! Jill then invites Cole to a Christmas party she’s going to that same evening and with Cole’s smooth reply, "I just might make a special guest appearance." From there, the rest was history.
Christmas was always a special time for both Cole and Jill. Their favorite thing to do together was going into Union Square and looking at the Christmas tree lights and watching the puppies in the window. December of 2019 was an extra special Christmas year because Cole and Jill had a son who was a little older and got to see the magic in all that Christmas has to offer. To Jill’s knowledge, it was their yearly tradition to go into Union Square but now sharing this tradition with her growing family and then.... With some careful planning and some white lies told and carefully planted with the help of the one and only Lauren Lagomarsino, I was able to pull off the proposal at the Xmas tree with friends and family, followed by a dinner at one of our favorite restaurants, John’s Grill. Mission accomplished.