First, let me state that I know shitting where you eat is one of the Cardinal sins; however, the client I am about to reference will no longer be my client after her next appointment.

That being said, is there anything I should be taking into consideration before I ask her out? She’s had about six appointments with me over the last year and has shown IOIs each time, which even led my receptionist to point it out after my client’s last appointment. I haven’t asked her out previously due to 1) I had a girlfriend and 2) I would never plate a client.

I’m thinking of saying something along the lines of “I know this probably wildly inappropriate, but would you like to grab a drink Friday night?”