Dear Irving on Hudson is a perfect place to get to know someone who might become more than a friend one day. The views are great, the cocktails are well-made, and there are little "seating stations" (made for two) that will make you feel like you're in your own little bubble as you try to figure out what the day's colors on the Empire State Building mean. This sister bar to Dear Irving takes up both the 40th and 41st floors of the Aliz Hotel Times Square, so there's plenty of space for big groups too. Most of the seating is indoors, but there are multiple open-air balconies. If none of the house cocktails sound appealing, order a bartender's choice. (You'll have to provide some details about what you're looking for.) If your date requests "something chocolatey and milky," then you'll know this is probably your last date together.