I'm half an inch taller than you (5'11.5" morning height) and have never used lifts. However, I'll often throw on boots particularly if the girl is over 5'7".
How's the comfort of lifts?
I am 5'8 and I have 2 pairs of "lift shoes". They are not "dressy" but also not casual. Sort of a boot looking dress shoe if you will and they go perfectly when worn with nice jeans from Buckle or AE and a button up untucked shirt.. Sometimes I wear them, sometimes I dont. If a chick is 5'6 or 5'7 I will wear them as they put me up around 5'10 or so.
They are actually comfortable. When I first bought them it felt a little weird because your on the balls of your feet more so than walking in normal shoes but its easy to get used to them.
As for the question about how a woman feels about you being a little shorter the next morning-
I could care less because they rarely see me the next morning as I am not into spending the night with chicks. I will say that plenty of time those shoes have came off around them after the date and I have yet to see any chick notice or say anything if they did notice.
Regardless of your height, if you want to wear them, wear them. Do what YOU want.