Lots of anti GP sentiment out there.I was surprised to see her on the cover and agree with another post that the editor's letter indicated that he thought there would be some backlash and wanted to get out ahead of it.That said I like the new Bon Appetit style.It took some
getting used to going through the previous issue on Italy.But I really enjoyed the writing,recipes and also the cooking tips such as how to prepare better pasta.I found the issue to be enjoyable to read and very informative.Lot's of recipes/techniques that I will try.I haven't entirely read this month's isssue,including the much maligned GP article.So can't comment on that but I do like the new style and thought last months content was excellent.

Your "friend" sounds like he has an incredible sense of entitlement, to the point where I would reconsider my friendship.I've been to group birthday dinners at restaurants many times and often the spouse or bf/gf pays for everyone.I've never been involved in a situation where the guest of honor issued the invitations,but it seems extremely tacky to me for the birthday boy to ask a bunch of friends out to celebrate and expect everyone to pick up the tab.Throw in the fact that his gf isn't helping to pay for at least part of the dinner and I would then decline the invite. It seems to me the fairest way to pay for the evening would be to split the tab by the total number of people in the party.This way everybody benefits from the two free dinners.The gf should at least pay for her portion if not her portion and his.

My brother and SIL live in New Paltz and my wife and I love going to visit them.In addition to beautiful scenery there are lots of good food options.Our favorite place is The Village Tea Room.The name is a little misleading.It has much to offer beyond tea service.We had dinner
there and the food and service were excellent.A very charming restaurant.My second choice is the Harvest Cafe.You can eat indoors or out depending on the season.It's located at the Water Street Market,which is a good place to wander around,The market has The Cheese Plate(self explanatory) and the Mudd Puddle is a good place for breakfast or just coffee.We've also eaten at Barnabys,which is a converted movie theater.There are many other restaurants in town that we haven't tried that look good.

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Mudd Puddle
10 Main St, New Paltz, NY 12561

Mark Joseph in the Financial District.Excellent food and service,although because of it's location it may be a little quiet on the weekend.But one of my favorite steakhouses.Also, Wolfgangs Midtwon.Located in the East 30s.Not as much of a fan of the Wolfgangs Downtown.

I had a cocktail that was called a Tensation that used Goldschlager.The approximate recipe was 2 oz Gin(the restaurant used Tanqueray 10),1/2 to 3/4 oz Pomegranate Molasses(could try with Pomegranate juice or grenadine instead),3/4 oz fesh lemon juice and 1/4 oz or so of Goldschlager.It was a very nice drink and the Goldschlager gave it a nice cinnamon flavor.Although at 1/4 oz a drink it will take years to go through your bottle.It's also not bad with Bourbon and Apple cider,either warm or as a cocktail.It can be useful in small amounts in mixed drinks.Especially this time of year.

Since you like cranberry juice,why not just add some vodka which is distilled to be flavorless.It's called a Cap Cod or Cape Codder,but most people just order it as a vodka and cranberry.You could specify a vodka brand such as Ketel One and cranberry, Grey Goose and cranberry,etc.

I've heard the bar at Porterhouse is nice and fairly quiet for a steakhouse,but haven't been myself.Some work friends like it very much.Places I have been that I think would work for a first date are Star Lounge at the Ritz Carlton and the bar/lounge at Southgate(which is in the Essex Hotel).Some restaurants in the area with a nice bar are Quality Meats (West 58th),The bar at the Modern (West 53rd), Ruth's Chris (West 50th), Beacon (West 56th),Piano Due (West 51st),
Thalia (west 50th).Other options are the various bars at the Plaza Hotel,Hudson Hotel bar and Library,

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Quality Meats
57 W 58th St, New York, NY 10019

Star Lounge
222 W 23rd St, New York, NY 10011

The only one on your list that I've tried is Le Compte and it's very good,although I've only used it as a mixer,but like it very much in a Sidecar variant.

I had a Singapore Sling last night and it was very good.Cherry Heering in a Blood & Sand is excellent also.Cherry Heering on it's own may taste like cough syrup ( haven't tried it straight) but it's a very good mixer in some classic cocktails.I don't know how it compares to Bols Cherry brandy.

Neither one is ideal for a wide variety of food choices.But both areas give you access to a few good dining options within walking distance and both are close enough to the subway that you are 10 to 15 minutes away from lots of excellent options.I would just go with whichever hotel looks better.Good food is easily accessible from either location.

I'm not a Carpano fan even though that seems to be the cocktail drinkers favorite.It has too much of a vanilla flavor for me, which I'm not big on.I've gone through two 1 liter bottles( at $30 a pop) and my opinion hasn't changed.My favorite cocktail is a Manhattan,with a Negroni (using Aperol rather than Campari) not far behind and I don't enjoy Carpano in either.Although when tasting sweet vermouth individually I do like Carpano more than most others.My favorites are Vya,followed by Dolin.Of the most easily findable I like is M & R.

When I've been there we've only had drinks and appetizer type dishes at the bar,which we've enjoyed.The dinner menu may be pricey.

So where did you end up going?

Not sure how to categorize it.Seasonal American I guess.Not a huge menu,but a mix of pasta,seafood and meat.We've been there a couple of times and sat at the bar.They have a good cocktail list, and interesting wines by the glass as well an extensive wine list.Everything we've had to eat has been very good(ravioli,lobster roll type dish,mac & cheese).There are several different areas.A lounge downstairs(haven't been) and the bar upstairs that overlooks(it's a step or two up from the floor) the main dining room. The space itself is pretty ccol and unique.When you come in off the street you walk through a narrow hallway that has small tables,chairs and bench seating.You can sit here and have drinks and small plates type food.You walk into the main dining area and it has a large vaulted ceiling with a large mural of trees on the back wall.It seems like the mural is backlit.It is an interesting room ,and the food/wine/drinks are good.It's pretty pricey but not outrageous.

It's tough to top Gramercy Tavern for great cocktails and food.Some other places are Gotham Bar and Grill, Piano Due (West 50s) which has a beautiful bar/lounge.High ceilinged room with a large bar in the center and a mural that wraps around the room.It is on a separate floor than the dining room.Also my wife and I have enjoyed drinks and food at Butter(East Village).

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Gramercy Tavern
42 E 20th St, New York, NY 10003

Gotham Bar and Grill
12 East 12th Street, New York, NY 10003

Piano Due
151 West 51st Street, New York, NY 10019

2nd the Thalia suggestion.Ate there before seeing Wicked with my wife and mother-in-law and we all enjoyed it.Nice atmosphere,good food and a variety of choices.As mentioned they have a burger and also house made pasta and a good seafood selection.

I ate at Il Gattopardo last spring and liked it very much.Very good food and service.We ate in the back area that has a glass ceiling.Very nice.Had drinks before hand at Beacon.A nice combo.

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Il Gattopardo
33 W 54th St, New York, NY 10019

A few others come to mind depending on what you consider old school. Some of these are from the 1970s/80s,but seem very NY to me.You mentioned you like the idea of jackets for the gents so maybe the 21 Club.
Steak: The Old Homestead, Delmonicos
Italian:Il Mulino,Patsys, Campagnola
Romance: One if By Land(this is bound to get some negative responses).
Chinese;Shun Lee Palace
80s heyday but still going strong: Gotham B&G,Aureole
Looking at your original post you already mentioned 21 and One if By Land.Sorry bout that.It helps to read the question first.

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21 Club
21 West 52nd Street, New York, NY 10019

Old Homestead
56 9th Avenue, New York, NY 10011

Campagnola
1382 1st Ave, New York, NY 10021

The Oyster Bar at Grand Central.Preceded by drinks somewhere on the Grand Concourse( I like Cipriani) and post dinner drinks at the Campbell Apartment.If that's too much drinking skip the Campbell Apt.

Sausage

I've eaten here several times and have really enjoyed it everytime.It can be pricey,especially with drinks as you mention but the food is good and I really like the decor/atmosphere. There are three separate dining areas.Four if you add in the wine cellar,which looks like it's setup for private parties.On the ground floor is a nice dining room,with a high ceiling and the tables are nicely spread out. Walk up the stairs and there is a bar with lots of table space for dining or drinking.Then on the top floor is another dining room.The way the restaurant is laid out each space is separate and distinct from the other ones.The food is good and service has always been excellent.My wife and I dine in Huntington often and this has become one of out favorite places to go.

Thalia at 50th/8th. Ate here pre-theater on a Sat. night and really enjoyed it.Good food and cocktails.Nice room. The menu is diverse with pasta,seafood,meat,etc.
Bar Americain - I believe it's 52nd/btwn 6th and 7th. I haven't eaten here recently,but went a couple of years ago before a concert at Radio City and the place was bustling.

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Bar Americain
152 W. 52nd Street, New York, NY 10019

The Lake House is very nice but a bit pricey.Entrees run high $20s to $30s.The poster asked for moderately priced places.Two restaurants that I like that are fairly close to your Aunt and Uncle are (1) Mamma Lombardis.Italian restaurant in Holbrook.The food is good,portions are huge and prices are reasonable.
(2) Porter's on the Lane in Bellport. Varied menu,good food,nice atmosphere,very good service.A bit more expensive than Lombardi's but should be less expensive than Lake House.

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The Lake House
240 W Main St, Bay Shore, NY 11706

I assume that you were coming into NYC this past weekend but if that's not correct there are several Italian restaurants that have very good food ,a nice casual atmosphere and relatively reasonable prices:
Pepolino ( Tribeca); Aurora ( Soho); Cacio e Pepe ( East Village); Il Gattopardo (West 50s) and Crispo ( West Village).

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Crispo
240 W 14th St, New York, NY 10011

Il Gattopardo
33 W 54th St, New York, NY 10019

Pepolino
281 W Broadway, New York, NY 10013

Cacio e Pepe
182 2nd Avenue, New York, NY 10003

I like Il Cortile, Angelos and Da Nico. Of the three I think Il Cortile has the nicest interior.

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Angelo of Mulberry Street
146 Mulberry St, New York, NY 10013

Da Nico
164 Mulberry St, New York, NY 10013

Il Cortile
125 Mulberry St, New York, NY 10013

Jane....Crispo.

As Kathryn suggested,Keens would be a good choice.A little bit of a walk to 36th/btwn 6th&7th.
Although it would likely run more than $200 for your group.
Becco,a Theater District Italian known for their pasta and very reasonable pre-theater prices. For burgers 5 Napkin burgers.In addition to a burger the menu has a pretty eclectic mix,including sushi and they serve beer,wine and drinks if needed.
Red Eye Grill may also be good for everyone. North of the Theater District at 56th near Carnegie Hall.It has a lively atmosphere and a varied menu.A good selection of seafood but also a burger,steaks,sushi.Something for everyone.

For the past couple of weeks I have been going through a new purchase " Mix Shake Stir:Cocktails for the Home Bar", a cocktail book based on recipes from Danny Meyer's excellent NYC restaurants.In addition to wonderful service and food,his places are known for their cocktails.This book has quickly become one of my favorites to flip through.The presentation is great with chapters such as Classics,New Classics,Elegant Sips and it has a chapter on cocktails for a crowd/party as well as recipes for interesting bar snacks.Most recipes are accompanied by beautiful photos.Along with "Art of the Bar",it is the most visually inviting cocktail book I own.It doesn't have the breadth of recipes that Joy of Mixology does,but it certainly has enough recipes to keep you happily mixing for a long time.I can't recommend this one highly enough for someone looking to entertain creatively at home or someone who wants to greatly improve their ability to put together delicious drinks.The only drawback is that some of the more creative recipes require homemade syrups or infused liquor or some not commonly owned liqueurs/ingredients. The homemade recipes are pretty easy to follow ,but there are enough other recipes that don't require anything too esoteric.I think this one has something for just about everyone.

Two places come to mind.(1) Quality Meats - Steakhouse on West 58th St. Meat-centric obviously but with some decent seafood options.Hipper decor/clientele than the typical steakhouse.(2) Bar Americain - Bobby Flay place on West 52nd St. Southwestern skewed "American Brasserie". Good bar,active room.I've only eaten here once,a few years ago.
Not sure what it's like now but it may be a good place for another date.

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Bar Americain
152 W. 52nd Street, New York, NY 10019

Quality Meats
57 W 58th St, New York, NY 10019

A few blocks walk to the west are (1) The bar/barroom at The Modern.It's at the Museum of Modern Art,West 53rd btwn 5th & 6th Avenue. Good drinks/food and a pretty cool setting.it's usually bustling but you would feel very comfortable there on your own.(2) Beacon restaurant, west 56th btwn 5th 6th Ave. Good variety on the menu with most entrees cooked in their wood oven.
Also I reccommend a 10 minute walk about a dozen blocks or so downtown to Cipriani Dolci at Grand Central.This rec. is really for drinks.I haven't eaten there,although they do serve food. It's located at the west end of Grand Central overlooking the Grand Concourse.One of my favorite places to have a drink or two while taking in the hustle and bustle of commuting NYers.There are other restaurants overlooking the concourse, Michael Jordan's Steakhouse and Metrazur, if you would prefer to have a meal there.

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Metrazur
Grand Central Terminal, New York, NY 10017

Cipriani Dolci
89 E 42nd St, New York, NY 10017