Next Stop Wonderland (1998)

Love is the destination.

Dumped by her loser boyfriend, Erin's love life hits rock bottom when her overbearing mother places an embarrassing ad in the "personals" section of a local newspaper on her behalf. Erin's disgust turns to curiosity as she searches for the right guy in a hilarious series of disastrous dates. Meanwhile, a lonely ex-plumber named Alan clumsily searches for his dream job while narrowly missing one chance meeting with Erin after another.