Some thoughts: In a dry place, humectants can work the opposite way, pulling moisture from your skin or hair out into the air, or from deeper layers of your skin out to the surface so you may need something more occlusive; and when my skin is feeling sensitive, mechanical exfoliating (,like your loofa) always makes it worse, but chemical exfoliation (like a toner with glycolic acid) usually no problem.
I can’t think of a best moment, though I’ve had a life that has gotten better over time, lots of good & great moments, none stands out as best.
Which leaves the worst moment, so I guess as an individual point it made a bigger impact.