Lover's Knot (1995)

Steve Hunter (Billy Campbell) and Megan Forrester (Jennifer Gray), unbeknownst to them, are being guided and "advised" by one of Cupid's caseworkers (Tim Curry), who has been struggling to get Steve and Megan together for many lifetimes. Cupid might actually have a chance this lifetime if it weren't for John Reed (Adam Baldwin), Megan's old boyfriend, who is determined to get her back. Add to this the conflicting advice of Steve's roommate, Nigel Bowles (Mark Sheppard) and Steve's temptation for Cheryl (Kristin Minter), a sensual coed, and it begins to look like this is one more lifetime Steve and Megan won't spend together.