Here are the few lines I'm thinking about:

  • "you look stunning today, I barely recognised you"

  • "wow, you look amazing when going out"

  • "you must get hit on all the time here"

  • "wow... You're a insert profession, a cute one at that"

  • "I can't believe he left you, must be crazy"

Or anything else along these lines. Some stronger than others. In other words you are implying she's attractive to you, but you are not saying it outright. The point I guess would be to gauge her reaction without risking rejection. Do you think these comments are endearing, fun, neutral, awkward or creepy?

If these are bad, could you suggest alternatives, or do you think one should just be more direct?