I've tried flirting, but have not found where my W's boundary is (for me) between what she interprets as unacceptable pressure and what is just light fun.
I have to admit that I have also never developed a talent for the sort of light, "so ambiguous that it would be acceptable in an office or with a friends wife" style of flirting that this would take.
But...
Joking with her about the "Exotic Bikini Wax" that we saw on a spa treatment menu ("are you going to sign up for that one...")is OK and gets a smile.
Saying "Wow! you look really HOT tonight tonight" as she heads out the door is not OK and gets a distressed look of unhappiness.
Me 42, W 39, S8, S6, S2 M 11y, A & ILYBNILWY 11/08 Walking away from a bad situation.