Here is an offbeat little 1998 gem for you rental folks. Written and directed by Brad Anderson ("The Machinist"), it features the prolific Hope Davis ("American Splendor, "About Schmidt" and "Infamous") and the always dependable Philip Seymour Hoffman ("Capote," "Before the Devil Knows You're Dead" and "The Savages"). The rest of the cast is comprised of B-level actors, although Alan Gelfant certainly wormed his way into my heart.
Boston-based Davis is devastated because she is being abandoned once again by her boyfriend, political activist Hoffman, who is leaving her to fight a new real estate development on an Indian reservation in Arizona. She is a nurse who had started Harvard medical school but abandoned her plans to become a doctor when her father died. Her mother, played by Holland Taylor ("Baby Mama" and "The Wedding Date"), has adjusted to widowhood and is living it up with a series of lovers and wants to see her daughter set free, as well. To that end, Mom places a personal ad for her in the local newspaper, much to Davis's dismay.
Cut to four young men -- two of them brothers -- who are partying together and philosophizing about whether or not their lives are foreordained. This scene is interspersed with one featuring Davis and some of her hospital co-workers holding pretty much the same conversation, with Davis taking the position that random events would interfere with anything foreordained.
This is a sanitized "Sex and The City" depicting the singles dating scene with all its tawdry disappointments, along with welcome scenes of both Davis and Gelfant actually working at their jobs. Davis in the hospital and Gelfant as a plumber for his father's firm, but volunteering at the local aquarium and studying to become his heart's desire: an oceanographer. Both are reluctant to date and both are vigorously opposed to the pretense of personal ads.
The scenes after she finally starts to listen to the responses to her ads are very funny. You get to see each caller in all his dismal glory as he creates the improbable picture of who he WANTS her to visualize. In the meantime, our hero is the target of an aggressive classmate who uses every ploy in the book to pretend he is actually dating her, e.g., she borrows his lecture notes after class then meets him for dinner to return them.
Of course Hoffman returns after a successful but ultimately disappointing trip. They have stopped the greedy developers but now the Indians want to build a casino, so Hoffman is back in Boston working as a pizza deliveryman. Obviously he wants to move back in with our gal.
I loved the soundtrack which featured Astrud and Joao Gilberto ("Girl from Ipanema") along with other Bossa Nova selections. By the way, Wonderland is a greyhound race track on the same transit line as Logan Airport, both of which figure into the story.
You have The Case of the Missing Puffer Fish, the inept aquarium guard, and there are a couple of through lines which are very clever and ultimately very satisfying. See if your rental folks have it available. I hope they do!