Meet Prince Charming (1999)

Jonathan Jack Harris is a waiter who hopes to start a newspaper called The Tribeca Times after the part of Manhattan where he lives and while struggling to find advertisers and stories decides to do one on Internet dating services so he joins one and seems to have found a great match maybe even a soulmate He doesnt know its actually his apartment block neighbor 29year old magazine editor Samantha Feld who only rolled into the thing because her friend and coworker Jen thinks she needs a man and threw a party at Samanthas place with whom he clashed from the start in daily life as they consider eachother noisy and inconsiderate Yet when they meet after email bliss together and nothing but failed dates with others