Congrats on a year! Sounds like you had a case of "what now?". I want to thank you for your post because I'm learning that I need to plan for the end of next May. Especially since it's going to fall around a long weekend and when everyone is having their beginning of the summer parties. Seems to be a common theme that this happens around anniversary points in time.
Interesting about the bartender. They have a job to do and as long as a person doesn't appear intoxicated their only business is to set that drink on the bar that you asked for. It was really refreshing to hear what he had to say to you. I'm glad that you made the decision that you did.