First, I believe this idea has promise-

-However, I am not sure what a “Quest for redemption” looks like. I know what a quest for a magic sword, or a quest to defeat the gods look like, but I’m drawing a blank at a quest for redemption.

Also if he’s on a quest for redemption you should tell us what he is seeking redemption from.

What did he do to need redemption and what must he do to get it.

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Here would be an example of what I’m talking about:

“After falling asleep on watch and allowing the enemy in the gates, a viking prince must hunt the barbarian invaders and save his sister who they’ve captured.”

We know know what (In my example) he did to need redemption and what he must do in order to make amends for his mistake.
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Hope that helped, good luck with this!

I just read you re-write, I like the “Happily ever after” part. The logline still needs a little something. We need to know why this is her last shot at love. (Or at least why she believes it’s her last shot at love)

“After a gypsy prognosticates she has one shot at true happiness, a woman who’s, “Unlucky at love” embarks on a date-from-hell with her foretold, one shot at happily-ever-after, hanging in the balance.”

Hope that helped, good luck with this!