Sidewalks of New York (2001)

The romantic fates of seven New Yorkers interweave as their lives and loves ebb and flow to the pulsing rhythms of the city they share. Tommy is a "bridge-and-tunnel" guy who yearns for a stable relationship after his breakup with a longtime girlfriend. Tommy gets counseling from the macho Carpo, but cruising the bars with Carpo is not what Tommy has in mind. Then Tommy encounters the gorgeous Maria, a spirited young teacher; sparks fly, but Maria is still smarting from the breakup of her teen marriage to Benjamin. Benjamin, in turn, has transferred his affections to sexy Ashley, a 19-year-old student and waitress. Ashley has her own affair going with married older man Griffin, a dentist whose blooming midlife crisis has not gone unnoticed by his beautiful wife Annie. Things come full circle when Annie, a real-estate agent, shows a loft to Tommy, kindling a flirtation that threatens to turn into full-blown seduction.