Our Story
October 15, 2022
First Date
After matching on 'The League' and rescheduling their first date three times (a strong start in modern romance), Jeff and Karen finally met at The Auction House on the Upper East Side — and it was immediately worth the wait. Over drinks, they discovered one uncanny connection after another. By the end of the night, it felt less like a first date and more like a long-overdue reunion.
January 29, 2023
Becoming Official
Despite a semi–long-distance setup and constantly conflicting schedules between trips, holidays, and work, Jeff and Karen decided to make things official. Soon after, they met each other’s parents and sisters — a crucial step, considering they both see their families approximately every waking minute.
July 15, 2023
First Trip Together
For their first big trip together, Jeff and Karen set out to explore the breathtaking beauty (and occasional chaos) of Croatia and Florence. Between stunning coastlines, hilltop views, and endless pasta, they also managed to collect a few “relationship-building” memories — a bout of food poisoning, lost luggage, and even a surprise reroute to Munich. Somewhere between the peaks and valleys (literal and figurative), they learned a few key lessons: Jeff discovered that hiking uphill in 95° heat is never a good idea, and Karen learned to double-check that they’re on the right boat before a sunset cruise.
July 20, 2024
Moving in Together
Not long after, Jeff and Karen took the next big step — moving in together. For Jeff, it was a major apartment upgrade (finally, a place with actual sunlight and an elevator). The transition was surprisingly seamless: Karen had real furniture, Jeff contributed real kitchenware and appliances, and somehow it all fit — both the stuff and the relationship.
March 25, 2025
Engaged!
After months of planning, Jeff finally popped the question in Central Park at proposal location #3. The proposal took longer than anticipated due to a 15-minute detour to watch street performers and having to bypass the first two locations because of tourist swarms. The best part came right after: celebrating with friends and family who made the day even more unforgettable.