With a boring wedding, attended by a guarded woman and a spontaneous man, starting a series of shared recollections of past heartbreak, Which Brings Me to You has all the elements needed for an early aughts romcom, releasing at a time when Y2K is trending. The original novel’s epistolary format is interestingly translated into flashbacks told in one whole day, with Will and Jane visually popping within the sequences as the two get to know each other through their past heartbreaks. It’s a unique idea, but the execution feels lackluster, with the dialogue and direction that can’t be saved through Lucy Hale’s or Nat Wolff’s efforts. There’s certainly something here about romance being a possible avenue to open up, but Which Brings Me to You doesn’t build the chemistry to get there.

With the source material, flashbacks are inevitable, but each sequence doesn't feel like separate revelations to learn more about Will and Jane– Instead, they feel like disconnected sets of multiple mistakes in love, without either of them actually learning anything. And to distract you from this, the film spends more on decent, but also tonally disconnected, soundtracks, rather than focusing on solidifying the duo’s characterizations or forming their relationship.