here's a new attempt. should i go back to bed, or just open a new bottle of wine?
Driven by nightmares and determination, naive and ill-equipped Jester Lewis resolutely confronts an alien menace. But can he summon the courage to face his budding love for Stark?
Better. I would probably drop the ill-equipped as it a) doesn't have enough context and b) is largely implicit in naivety.
The second sentence is a curveball. it undermines the strength of the first by changing the direction entirely, and introduces a character in the last word for whom we have no context.