Not sure if it’s too late, but I am new to HO, and just found this thread.
You mentioned interest in steak and fries — I suggest Le Crocodile in Williamsburg. They also do an excellent roast chicken and fries. Overall great French bistro food. Great ambiance too.
For Steak Au Poivre, I might consider Red Hook Tavern in Red Hook. They also do a very unadorned, very good, and rather expensive burger.
Staying in Red Hook (my neighbourhood), I see you’re already familiar with Hometown BBQ. Bar Mario opened quite recently, and offers good, traditional, Italian. Sunny’s Bar doesn’t have food, but you should go there one evening for their live music night. Sensational NYC vibe. Grindhaus is an unclassifiable cafe/bistro/restaurant owned by a truly colourful character who lets her chef run riot with flavor combinations. I always find a meal there ‘interesting’. Seaborne is an under-the-radar cocktail bar serving very good drinks (no food).
Someone already mentioned Somtum Der, which indeed is a nice alternative to Ugly Baby. If you really want to go to Ugly Baby (the spice levels are crazy but I admire the chef’s uncompromising standard), then try the Penang Curry — it’s IMO the most manageable in terms of spice levels.
I also suggest La Vara and its sister restaurant Saint Julivert for superb seafood cooked in very modern and inventive ways. I’ve basically never had a bad meal at either.
Finally, also suggest Place de Fetes for neo-bistro/wine bar/inventive modern American vibes and food. Menu changes often, but always interesting and, more importantly, delicious.
You mentioned Dhamaka — the same restauranteur runs a place in Brooklyn called Masalawala, focused on Bengali food. Kind of a limited menu, non-existent vegetarian choices, but both the wife and I loved it.
I saw Pecking House mentioned — second that it’s great fried chicken. For a different style, try Rowdy Rooster in Manhattan — counter ‘Indian’ fried chicken spot run by the same Dhamaka guys.
Hope that helps.