Clear Cut Couples: Ali and Jake

Like many young New Yorkers, Ali and Jake met on a very romantic dating app, Bumble 😉. They have a common friend so they were able to do a little bit of recon before their first date.


Their first date was at a cozy speakeasy above Five Guys in the West Village. It’s still one of their favorite places! What they both expected to be a drink or two ended up being a five hour date with no shortage of cocktails or questions. They have been together for over six years since then! “He was worth the wait,” says Ali. AWW! They have shared countless incredible memories over the years. They fell in love eating, drinking and laughing their way through many cities, including their home, NYC. Their first trip together was to Savannah, Georgia where they learned that they loved traveling together despite the fact that Jake likes to get to the airport 5 hours early (LOL).


One of their favorite trips is always heading upstate to Hudson, NY. They try to make a long weekend trip every year, so it holds a special place in our hearts. A special moment for them was moving in together in Williamsburg. They had the best time making their apartment their home & love spending time together there, even through the pandemic in such close quarters.


On Christmas morning, Jake surprised Ali by driving down to Annapolis, Ali’s hometown. When Ali returned from church, she saw a sign hanging on the Christmas tree that said “want to hang with me forever? xoxo Jake” Jake popped the question, Ali said of course & then they spent the day celebrating with friends and family.


It was a total surprise! Ali never expected the proposal to happen in Annapolis or on a holiday, but Jake knew it was important to have the families there for the big moment. They couldn’t be happier that they got to spend that special day with the people that matter most to them.


They said, “We both haven't stopped staring at the ring. It’s perfect!” As for their wedding, they are hoping to enjoy the engagement bliss for a bit but plan to have the wedding in Annapolis at some point. Congrats you two! We are SO happy for you!

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