Sweetest woman in the world is retiring after a forty-year career as switchboard operator & receptionist. Asks can she have her send-off party at the Midtown Olive Garden, her favorite restaurant. The President of the company (legendary 80 year old denizen of NY theatre world) says no, there are better places & does she mind if we have Italian elsewhere. She says ok. The President of the company then suggests I will find that better place and make everyone (approx. 50
people, including him/his wife/their invitees/receptionist's extended family/etc.) happy.
The restaurant doesn't necessarily have to be located Midtown, but should be easily accessible via subway & in Manhattan. Ideally it would have a private room, a very good Southern Italian catering menu, and an easygoing ambiance. Carmine's has come to mind, though I'd like to do better for her if I can--somewhere small, intimate & excellent would be ideal.
Obviously this is much a sociological as culinary challenge, but any suggestions would be appreciated.