You're asking the wrong person...but I"m answering anyway! LOL. Michael Buble for sure!! But I say that because I love his music enough to suffer through sitting in nosebleed seats despite being absolutely terrified of heights! :o
In all fairness, as I'm hopelessly fanatical about M.B. and you may not be, I guess it boils down to are you more interested in comfort and a pleasant experience on the town with your man, versus seeing and hearing an act you haven't experienced before.
I guess you need to ask yourselves, what do you hope to gain from your date together? Memories and a predictible but solidly good evening at Wicked, or a chance at something different, probably fun, but probably not perfect as far as accommodations not entertainment goes (however his music can be romantic and that might make up for the less than romantic seating).