Im goint to NYC with my boyfriend (his first time there) to celebrate his 24th b-day. I wanna take him to a nice (not too expensive <$100), romantic, cool restaurant or bar/lounge. Any suggestions? (we're staying near Times Square)

Before somebody else does may I suggest that you repost this question and make your thread appropriate to you question such as "NYC romantic restaurant for birthday celebration".
That way your thread will catch the eye of Fodorites who are familar with NYC restaurants.

I think you have to decide whether you want a restaurant, a bar, a lounge or all 3.

The Times Square area is not known for "coolness." Most of the cool places are downtown although there are a few trendy hotel bars in the area. The Blue Fin restaurant in the W Times Square hotel is good (if you like seafood and sushi) with a good bar too, but it's loud, so not what I'd call romantic.

Zanzibar is a bar, lounge & restaurant. It's in the area known as Hell's kitchen, just west of Times Square. Read about it here
http://nymag.com/listings/bar/zanzibar/index.html

If you'd like to go to a restaurant first and then a lounge, Candela is a nice romantic restaurant near Union Square that's not too expensive.
http://nymag.com/listings/restaurant/candela/index.html

West is a bar/lounge on the Hudson River with nice views, good drinks and romantic atmosphere.
http://nymag.com/listings/bar/west/index.html

I think you'd like going to The View revolving restaurant at the top of the Marriott Marquis. We went there for drinks recently, and it was quite "cool." There is also a restaurant on the level above/below ( ? ), but the buffet in the lounge looked quite nice, and many people were partaking. It looked like a lot of appetizers, salads, and wonderful desserts.

The view at the View is great, but the food is not and it's pricey. Great for a drink, but go elsewhere to dine. It's not at all "cool" as in trendy.

What was it Gekko said yesterday? That Columbus Square is the hotbed of coolness?

LOL!

Thank you for the tips!
Has anybody heard of a place called Sugar?