Dear M.,
First let me say that I absolutely HATE the separate check idea. As a professional I can't tell you how many times I use to go out with a group of (usually) women and have people bickering over who had this or that. It was frustrating and embarrasing. So I came up with a plan that has worked well for years. It requires some organization, but you seem to be on top of that.
When you are expecting participants to pay for their own meal and/or share the cost of the guest of honor’s meal, there is NOTHING inappropriate in being crystal clear, if fact it will be appreciated. It also helps if you can plan the menu ahead, get the restaurant to give you a price per person including tax and tip. Give people a choice of meat, fish, chicken, vegetarian etc, (dinner should include soup or salad, coffee/tea and dessert). If you wish to include wine (1 bottle per 4 guests), make it clear.
EXAMPLE:
Event: Dinner With Jennifer
Where: Frankie and Johnnies
1111 Main St.
Ourtown, USA
Phone: ###-###-#### (Restaurent phone - incase someone gets lost or can't attend at last minute)
Date: Feb 14, 2009
Cocktails: No Host Drinks at 7:30 PM
Dinner: 8:00 PM (Cost Per Person - $42.00
price covers dinner, wine, tax/tip and Jennifer’s dinner)
Ladies, Please pay separately for any additional alcoholic beverages.
(Make sure your waiter knows the game plan)
RSVP: M. D. - ###-###-#### by this date _______