When JACK GOES BOATING debuted at Sundance earlier this year, the audience gave it a standing ovation. It’s easy to see why. As a story that’s really three stories in one, JACK GOES BOATING lifts you up and sends you way back down again with its sweeping narrative of two friends and two sets of lovers, one old and doomed and one fresh and new. It starts with Jack, played by Philip Seymour-Hoffman, who also makes his directorial debut with a script based on Robert Gloudini’s play of the same name, which Hoffman also starred in. Jack’s friend Clyde (John Ortiz) sets him up with Connie (Amy Ryan), his wife’s co-worker. Connie is a timid, delicate, mouse of a woman, with insecurities so obvious they make her the victim of multiple instances of sexual harassment, even assault. She’s one of those women, coming upon middle-age, still unsure of who they are, making her an eligible candidate for Jack, who drives a limo and lives in his uncle’s basement.

What they have in common is that they’re both stuck in a rut but want to better versions of themselves. Jack is trying to get a better-paying job at the MTA and Connie steadily improves as a telemarketer for group grief counseling sessions. When they meet it’s as awkward as you might expect, ending in Connie’s near nervous breakdown in the bathroom. But Jack and Connie find a warmth in each other – a need to comfort and be comforted – and slowly, very slowly, they managed to coax those feelings into the makings of a meaningful relationship.

One of the relationship’s first caveats is that Connie wants Jack to take her out on a boat. Jack doesn’t know how to swim, but as it’s winter he has several months in which to learn. Clyde offers to teach him, and so begins relationship number two. During the swim lessons the two men are remarkably gentle with each other. Jack is open to the new experience of swimming and Clyde is kind, sympathetic and encouraging. Their time spent together naturally brings them closer, even if they have different ways of showing it. Clyde is effusive (I love you man! My man Jack! I love you!) and Jack is more reserved. It’s not long before Clyde opens up about his deteriorating relationship with his wife, Lucy (Daphne Rubin-Vega), and after Clyde reveals Lucy’s numerous past misdeeds, Jack can’t help but become involved, though it’s clear he’d prefer not to.

Even though Clyde and Lucy’s spiteful, resentful relationship provides a good contrast to Jack and Connie’s brand newness, and even though Ortiz gives a knock out performance, it starts to weigh the three-part balance down in a direction that’s distracting to the film’s main stars: Jack and Connie. Because their relationship is so fresh and delicate and light, it’s easily overpowered by Lucy and Clyde’s drug-induced all-night, all-out scream fest. Is this supposed to make what Jack and Connie barely have yet seem more special? Instead it invites skepticism, so that when Jack and Connie walk off together in the final scene leaving Clyde behind them, they’re cloaked in a shadow of doom rather than awash in the bright ebullience of a relationship as of yet untainted by past misdeeds. They’ve spent the whole film being warned of the evils of relationships, and as they walk away, arm in arm, you want to warn them shout after them “Good luck. You’re going to need it.”