My older son turns 18 this year and heads off to Miami of Ohio. Sadly, he will not be home on his birthday, as classes begin that week. While discussing what he'd like for his birthday, we heard "I want to eat in a real Manhattan steak house". No argument from me.
There are plenty to choose from. Keen's, Smith & Wollensky, The Palm, Peter Luger (technically Brooklyn, but one of the originals), The Strip House, Sparks (I worked across the street from Sparks in 1985 and heard the shots that killed Paul Castellano - we all thought it was a car backfiring), Del Frisco's and The Old Homestead are all top notch. After some discussion, the choice was The Old Homestead as this is a classic, original New York steak house.

Each time the boys come to New York, I make them navigators. Subway maps are analyzed and paths charted. We rode the subway up to my office, spent a few hours working, then walked 50 blocks to the restaurant to meet my wife.
When we walk in New York, I like see if they know the section of the city we are walking through. It's a test to see how observant they are, or test their memory. It's also a great way to learn the history of Broadway (an old Indian trail), how many squares it runs through and their names (4, Union, Madison, Herald, Times) and experience the hustle and bustle of a major thoroughfare. We passed Lincoln Center, Columbus Circle, Madison Square Garden (hasn't been in Madison Square for years), the Post Office, the Hotel Chelsea and the Chelsea Market on our route.
To the boys it was a "Bore Tour" with dad, just a long walk to get dinner.
Upon arrival at the restaurant, we had some time before my wife would get there. We waited at the bar and I noticed a person eating dinner next to me, so I whispered to my son. He leaned over to take a look and his eyes lit up.
It was Kevin Connolly from the HBO program Entourage, not a show I watch, but I am familiar with his work.
I don't bother celebrities, so I avoided speaking to him. That changed when he ordered a second plate of whatever it was he was eating, and commented how delicious it was. I had to find out what he was eating, and asked. Kobe bacon, he replied, and he was losing four years of his life eating it. I laughed, and we struck up a conversation, which my boys joined. We didn't once mention the show, who he was, or ask for a photograph. I thought that would be a little too crass, even though he was a very likable fellow. He left minutes before my wife walked in, with a cheerful farewell and wave. My sons were very pleased...until the bartender told us he loved having photos taken. Missed opportunities happen, but I don't worry about them. We were being polite and trying to respect his privacy, I can't feel bad about that.
My wife arrived, and we were taken to our table, where the boys filled her in on their brush with celebrity. Then the talk turned to the steak house itself and the food we were to order.
The Old Homestead is what you think of when you think steak house, and I've eaten there several times. It went through a renovation four years ago. When I first ate there in the 80's, the first floor was a huge room with dim, smoky lighting and lots of wood. Today, it's got three floors of dining and new tin ceilings and paneling. It has an updated style, close to the original decor, though I miss the old style New York chop house. It's remained true to the feel and look, just newer and cleaner looking.

The meal was excellent. Mashed potatoes, onion rings, and the recommended Kobe bacon, all on the side. For entrees, my younger son had a Gotham steak on the bone (ribeye) while my older son and I ordered the 22 oz. on-bone filet mignon. This is really just a Porterhouse cut in half, since filet implies no bone. It's become a popular offering. I was introduced to it four years ago and I've become a fan of the bone-in filet. Medium, of course. My wife ordered sea bass, and cleaned the plate.
My wife had a glass of Cabernet from Argentina, Vicien 2009 with her meal. I had a pint of Old Homestead Amber Ale, which is brewed upstate for the restaurant at a microbrewery.
As birthdays go, it was a success on many levels. The boys enjoyed themselves and the meal, and there was plenty to discuss on the ride home. It was the kind of experience he'll be sharing with his new friends in a few weeks. I was pleased that they got more exposure to New York, enjoyed a great chop house, and had one of those rare experiences which make for great stories with friends.