The John Hancock dining room faces East and somewhat south as I recall (the ladies bathroom faces directly south and you walk in and apparently walk right up to the window thinking it is a mirror the wooooow window 96 stories up! many women come back ashen faced and say they hugged the walls!).

The lounge I recall is on the same floor as the restaurant (sky deck is the floor above) and the lounge faces south, north and WEST for sunsets!

Take her there for a bottle of Dom at sunset . then have dinner reservations as others suggest.

Sears Tower only has an observation deck . no drinkies!