At least they get off to a good start - introductory membership to the Mile High Club in a toilet cabin thousands of feet above Middle America.
But after that, any spark between Emily (Peet) and Oliver (Kutcher) appears to go into freefall when they can't seem to make any connection.
An impish Goth, she's happy sloshing away an afternoon with a bottle of bourbon while he's got firm goals and a career path mapped out.
Three years after he's scribbled down his phone number after their one date, Emily - emerging from a broken relationship - gives him a tentative call.
It turns out he's not a captain of industry after all but living with his mum and his bolshie sister…and only to happy to spend New Year in Los Angeles with Emily.
However, come the morning he's off to San Francisco to make his fortune running a website selling nappies.
Over the next few years we follow the loose couple as they move jobs, change partners and run into each other only for circumstances to pull them apart.
Director Nigel Cole showed he could craft a quality comedy with Calendar Girls but this script - from newcomer Colin Patrick Lynch - struggles to stay afloat.
Kutcher, fresh from his impressive show in Guess Who, demonstrates again he's a leading man of some subtlety and Peet engages, even if all she's required to do here is act goofy and neglect to wear a bra.
It aims to be a sort of When Harry Met Sally for the dotcom generation, but rather than build to an emotional climax is runs out of steam well before the final reel.
Perhaps, it just goes to show if you are going to fall in love…try to get the dialogue right.
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