147 West 43rd Street
You have a bit of a dilemma on your hands. You have finally met that awesome girl (or guy) and want to treat her to a night on the town. Maybe take in a Broadway show at 50 percent off (see NYCheapskate.com's other deals), or a movie on 42nd Street. First, you need to eat. Where can you go in midtown that won't break the bank, but also won't let on that you're a cheapskate?
You can stay classy, and even romantic, by taking her to Tony's Di Napoli, a long-time favorite of the Broadway theatre crowd. This family-style restaurant means you can score a pasta dish for $18 to $25 -- the kicker is that each dish serves 2-3 people! You can literally have a semi-upscale date at this bustling Times Square establishment for under $40. Hell, skip the booze and you can make it under $30 for two!
Try the chicken scarpiello for $19.95, or salmon ala vodka for $26.95. The portions are generous, and they'll give you decent bread as an appetizer. Tell Tony that NYCheapskate.com sent you, and you won't get any kind of special treatment.
(Note: Secondary UES location at 1606 Second Avenue)
Amazing deals on apartments are lurking right around the corner, if you know where to look, and when.