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 soul-mate. He doesn't know it's actually his apartment block neighbor, 29-year old magazine editor Samantha Feld -who only rolled into the thing because her friend and co-worker Jen thinks she needs a man and threw a party at Samantha's place- with whom he clashed from the start in daily life as they consider each-other noisy and inconsiderate. Yet, when they meet after e-mail bliss together and nothing but failed dates with others...