Clear Cut Couples: Jenny and Jay

Jenny and Jay met on Hinge two weeks after Jenny had moved to Charleston from Manhattan. They were immediately shocked by the number of seemingly odd connections in the paths that brought them together… Jenny was named after Jenny Lake in Jackson Hole, WY; Jay had worked there as a ski instructor and it was his favorite mountain to ski in the country. Jenny had spent childhood summers visiting family on Martha’s Vineyard, just a few miles away from where Jay was born and raised on Cape Cod. 

It turned out that Jenny was a sorority sister of Jay’s close childhood family friend at Elon. All of these connections kicked off the beginning of their journey!

Their first date was at Elliotborough Minibar in Charleston. They shared drinks and chatted during Open Mic Night. The rest is history! They have been together for 3 years since then. Little did Jenny know that Jay would be playing live for her there in a few months’ time.

They have shared countless incredible memories over the years. They’ve been lucky enough to visit their favorite places, Jackson Hole, Cape Cod, and Martha’s Vineyard, and explore new places together - seeing Taylor Swift in Milan and touring Piedmont last summer was definitely a highlight! Outside of travel, adopting their golden retriever, Hootie (@hootiethegoldenpup) a year ago has been a huge highlight of their relationship. Finally, being blessed with some amazing friends and family that they have been able to spend a lot of time with over the past couple years.

Sunday 7/27, Jay managed to surprise Jenny with a beach proposal in her hometown in Connecticut. He had the ring in his possession for all of 24 hours. Knowing Jenny was thinking it was going to be the following weekend at the earliest, Jay took advantage of being in Jenny’s hometown with her parents present. It was a quiet proposal on her favorite beach with just the two of them. They celebrated with her parents and Jay’s mom, who made the 3-hour car ride down from Cape Cod to join Jenny’s parents for the surprise.

It was a huge surprise! Jenny’s reaction was a resounding YES and the ring exceeded her wildest dreams. Jenny was shocked to hear that she had “seen this stone before” and it was the exact one that had been featured on The Clear Cut over a month earlier.

They are aiming to get married in September of 2026. Likely in Charleston or Cape Cod! Congrats you two! We are SO happy for you!