After a rocky "first" meeting, Henry and Clare attempt to reset with a second date, but she still struggles to rectify this version of Henry with the man she's known – and loved – all her life. To help her better understand the difference between this 28-year-old and the man she'll help him become, Henry takes Clare back to the most formative moment of his childhood.

Clare hosts a couples' dinner party to introduce Henry to her roommate Charisse and best friend Gomez, but when it's crashed by another Henry and his girlfriend Ingrid, deeply held secrets are revealed. Meanwhile, Clare remains determined to make her 18th birthday and fated 152nd meeting with Henry in the clearing unforgettable.