Lieberman in Love is a 1995 short film (barely, it got under the 40-minute AMPAS cutoff by thirty seconds) directed by Christine Lahti.
Joe Lieberman (no, not the former Senator!) is a 50-year-old widower, picking up the pieces nine months after his wife died. He's also rich enough to spend an apparently indefinite amount of time in Hawaii and say "price is no object" when shopping for Hawaiian condos.
Joe (Danny Aiello) is in fact spending an indefinite amount of time when he approaches Shaleen (Christine Lahti) at the hotel bar. Shaleen says politely but firmly that her time is expensive—in other words, that she's a prostitute. Joe is retreating in embarrassment when Shaleen points out that he was going to spend money on her anyway in hopes of sex: instead of spending the money on a fancy dinner for two and wine, why not just pay her directly and be sure of sex?
So he does. In fact, he becomes one of her regular clients. Joe, apparently wealthy enough to retire to Hawaii at age 50, starts shopping for condos. His real estate agent is a golden-haired beauty named Karen (Nancy Travis). Joe finds himself falling for Karen, but Karen is married. So Joe enlists Shaleen the hooker, paying her fifty thousand dollars to seduce the husband and break up Karen's marriage.
Based on a short story by W.P. Kinsella, who also wrote the novel that was the basis for Field of Dreams. One of only three films directed by Christine Lahti, who spent most of her career as an actress on TV shows like Chicago Hope.
- Anguished Declaration of Love: Joe, gobsmacked after he finds out that Shaleen paid Karen fifty grand of her own money to get lost, says "Is this a declaration of love?" Shaleen, tears streaming down her face, says "So what if it is? So what?"
- Betty and Veronica Switch: It seemed like sweet and innocent Karen was the Betty and cynical prostitute Shaleen was the Veronica—they're even color-coded that way, with Karen's blonde hair and Shaleen's dark reddish-brown. But it turns out that Karen is a money-grubbing schemer. Shaleen picks up on this and gives Karen $50,000 of her own money, the money that Joe paid her for the job, so that Karen will get out of Joe's life. (Karen soon scams $50K more out of Joe.). Why did Shaleen pay Karen to go away? Because Shaleen is the real Betty and has fallen in love with Joe.
- The Big Damn Kiss: The Anguished Declaration of Love is followed by The Big Damn Kiss, which is followed by Joe pulling back and realizing that it's the first time they ever kissed. Shaleen, shocked, says that hookers don't kiss—and then kisses him again.
- Dogged Nice Guy: When Joe can't get pass first base with Karen he plots to artificially engineer this situation. He will get Shaleen to seduce Karen's husband so that Joe can swoop in and console Karen afterwards. He eventually finds out that he misjudged the situation badly.
- Flashback: Joe thinks that Shaleen double-crossed him by taking $50K from him to break up Karen's marriage, then—according to Karen—demanding $50K from Karen to get out of her husband's life. A flashback reveals what really happened: Shaleen, who has figured out that Karen is a schemer looking to bleed Joe for money, offered her the $50K that Joe gave her in return for Karen going away.
- Karen's failure to pick up on Joe's Shirleen/Shaleen I Never Said It Was Poison blunder with names foreshadows that Karen actually knows Shaleen's name and is lying to Joe.
- Shirleen has a candid talk with Joe in the beginning about men spending money indirectly to have sex with women—taking them out, buying them dinner and candy and flowers—when they might as well spend it directly on sex. The ending reveals that Karen was scamming money out of Joe indirectly.
- High-Class Call Girl: Shaleen is a high-end hooker and she's not at all ashamed about it. Joe, who's pretty rich, becomes a regular client.
- Hooker with a Heart of Gold: Shaleen denies this specifically, saying "I don't have a heart of gold." Until the end, of course, when we find out that she does.
- Hula and Luaus: The first shot of the movie is the shapely backside of a hula dancer as she shakes it at a luau—pan over to the fat butt of the tourist jiggling next to her. Near the end of the film, Shaleen and Joe stumble into another luau as Shaleen explains what went down with Karen.
- I Never Said It Was Poison: Averted. When a weeping Karen tells Joe about how someone named "Shirleen" seduced her husband, he automatically corrects her, saying "Shaleen." Karen totally misses this—or maybe she doesn't miss it. The ending reveals that Karen not picking up on the name was Foreshadowing.
- Malicious Misnaming: Karen keeps calling Shaleen "Shaboom", even after Shaleen corrects her and threatens to punch her if she does it again.
- Off-into-the-Distance Ending: Ends with Shaleen and Joe, having admitted their love for each other, walking away down the beach.
- Swiss Bank Account: Shaleen has made enough money as a High-Class Call Girl that she's socked it all away in a Swiss Bank Account and anticipates that she can retire before she ages out of hooking.
- Time Passes Montage: A series of scenes where Joe is shown saying "no" to various condos. (He's clearly more interested in time with Karen.)
- Unproblematic Prostitution: As Shaleen explains, she's good at it, the men are satisfied, she makes a lot of money and she's going to retire young.
- Vacation Episode: A rich widower retiring to Hawaii finds himself in a love triangle.