However, my hours of research and some bar scoping paid off and I of course wanted to share my insight with you in case you are looking to plan a similar event.
190 1st Avenue between 11th and 12th streets
Tree has been a longtime favorite of mine for their year-round garden, outstanding service, and simple yet elegant food. They could not have been easier to work with and assured me that they accommodate large parties often. They even do weddings! As such, I simply made a reservation for 18 people via email (which changed to 15 the day of with no penalties) and they allowed us to order off the menu--no required price fixe and no deposit whatsoever. It was like living in event dream world!
As for food, I'd highly recommend the "Sunday Morning" flatbread ($16), duck meatloaf ($22) and Cookies and Cream Panna Cotta ($7).
Here we all are at dinner:
133 Avenue C between 8th and 9th streets
For after dinner drinks I wanted to find someplace close to the restaurant without the college and post-college vibe that plague many East Village bars (not that there wasn't a time and place for that in years prior!). A friend and I did a Monday tour of 4 bars in the area and settled on The Summit Bar for it's clever but not rip-roaring expensive cocktail menu, the friendly bartenders, and (again) the ease with which it was to make a reservation. The long, skinny bar can section-off either the front or back areas, and I chose to go with the front because it is surrounded by tables which makes it semi-private and is close to the bar. All I had to do was call up a couple weeks in advance and let them know how many people--no deposit necessary and no penalties.
I would highly recommend both the Sutter's Mill ($12 - Buffalo Trace Bourbon, Cinnamon Agave, Pineapple, Lemon) and The Guv'nor ($12 - Famous Grouse Scotch, Buffalo Trace Bourbon, Toasted Cardamom Infused Agave, Japanese Yuzu Juice, Orange Juice) cocktails.