It all started in Aspen. While Sam was there for work, he saw and commented on a picture of Jess taken in Aspen. Hours later they matched on hinge and Sam worked up the courage to ask Jess out for drinks. She said yes. Their first date took place on 2.10 after Jay’s birthday dinner even though Jess considered cancelling due to a full tummy. Jess and Sam had a great first date at Goodnight Sonny in the East Village. And so the romance began.

Knowing Jess' dream has always been to go to Blue Hill at Stone Barns, under the guise of Sam’s birthday, Liz and Alex decided to "surprise" Sam with a picnic lunch for his birthday present. Upon arrival at BHSB, Jess’s initial reaction was verbatim, “wow, what a missed opportunity for an engagement!” Little did she know that was just the plan. While Sam was trying to whisper sweet nothings saying how much he loves her and the life they have built together, Jess was focused on taking in the historic, beautiful farmhouse and scenery. It wasn't until Sam bent on one knee that Jess fully grasped her dreams were all coming true. and Jax's too :)