I ll Take You There (1999)

Bill Baylor (Reg Rogers) is struggling to make ends meet in his Manhattan real-estate business when his wife and best friend run off together, thereby flushing Bill's personal life directly into the same toilet his career has been circling. The down-and-out New Yorker finally gets a brief pick-me-up when his sister sets him up on a blind date. But happiness is fleeting when Bill realizes his date (Ally Sheedy) is an old college friend with whom, surprisingly, he no longer has anything in common. After Bill rejects her, though, he seems to have gained a stalker. This quirky comedy from writer-director Adrienne Shelly is about the unlikely events that can put major life changes into motion.