I'm going to lunch with a college educated man (a classmate) whom I would like to get to know better. Lunch came about because we'd emailed several times about discussing events for an upcoming college class reunion. I was able to get the final piece of info that we needed and emailed him. He called last week and asked me to go to lunch. He seems like a take charge kind of person, which I like. He asked what I like to eat and what time I'd like to go. He said he'd call the day before to confirm with several restaurant choices. I have no problem with conversation, but I don't want to be overly desperate. Since we are meeting to discuss "business" should I casually ask about my portion of the check when it comes or will this turn him off? Or, at the end should I say "the next meeting is on me." I really want this to work. Any tips? -Lunch Liasion

Dear Lunch Liasion,
The only way you're going to offend him is by insisting on doing things your own way regardless of his viewpoints. As you are both casual acquaintances it would be proper to offer to pay your portion of the bill. What I have done in similar situations is just ask while we are deciding what to eat if they want to get separate checks to make the bill paying easier. This lets the other person know you are willing to pay for your half, and gives them the opportunity to offer to pay for the entire thing. If they do offer to pay, a quick and sincere, "Are you sure?" will suffice for the "mandatory" quibble. The biggest benefit of getting it clear during the order process is you're able to relax and enjoy the rest of the meal without worrying over how to handle the bill paying etiquette.

With Love,

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