The Prince of Hearts/Jacks + Ironic Twist π
The answer? Until there's no turning back.
As much as I think Jacks tries to deny it, he is looking for a Happily Ever After just like Evangeline. It might not be the perfect picture that Evangeline envisions her Happily Ever After, but it still concerns requited and unconditional love.
The Prince of Hearts represents broken hearts and unrequited love for other people. But to Jacks himself it also means he's doomed to suffer the same fate.
I want to go further into his characterization because I think he as a character who has a lot of subtleties to unpack. I'll start in the rough order of the timeline of all three books (two of the Caraval trilogy, and OUABH)
Spoilers to Legendary, Finale, and Once Upon A Broken Heart.