It’s December 12, 2019. The people of Boston were gearing up for the next three months of cold, frozen gray slush while eagerly chatting about Tom Brady once again in the playoffs. No one had ever even thought about disinfecting their groceries or worried about running out of toilet paper. Truly a wonderful, magical time in Massachusetts.

After a late night of working in Copley, Ty headed over to Lolita’s. It was here on this frigid night in Back Bay in a basement bar that he would meet Kyra for the first time. They shared many margaritas, looked at embarrassing driver’s licenses, and excitedly chatted the night away. Eventually, Ty walked Kyra to the train where she would play the night over in her head and think on about how great that Long Island (pronounced Lawn-guy-lan) guy was the whole ride to Needham. Little did either of these chilly, star crossed, soon-to-be lovebirds know this was the last First Date they would ever go on.

Two weeks had gone by and they had already been on two more dates and sent hundreds of texts and Instagram DMs with deep and insightful comments like, “omg this is so you”. Ty then decided to leave a vacation in Nashville and come back to Boston for NYE where he met Kyra at a house party. It was here he was sized up by the scariest and most formidable people to ever brunch in Southie, the former graduates of Needham High, aka Kyra’s friends. Somehow, Ty must have passed their test of approval as he and Kyra got to watch the ball drop and take their first ever photo together (see the timeline for embarrassing proof).

A few more weeks of grabbing drinks at Bell in Hand, ice skating, and seeing a concert at the House of Blues, and Kyra was off for one of her many, MANY, trips around the world. It was only after a month of FaceTiming in different hemispheres and coming back from Southeast Asia that Kyra would ask the question most millennial men in Boston in their 20’s dread, “What are we???” It was on this day, February 29th, that Ty would make the greatest decision he has ever made and proclaim to Kyra that he would be honored if she would be his girlfriend. The two, positively giddy, began doing what every Type A relationship does and planning out all the cool activities and bars and dates they would go on in March of 2020…and the rest is history.

Accommodations

Newport Marriott Hotel & Spa

Air bnb

Wyndham Newport Hotel