Cameron Crowe’s Singles wasn’t popular enough to be an unambiguous inspiration for the TV mega-hit Friends. But, looking back, the pieces are there.

The 20-something leads of the 1992 film, Crowe’s follow-up to 1989’s Say Anything, all live in the same quirkily set-dressed building, hang out at the same hip coffee shop (where at least one of the group works) and have an entwined romantic history. There’s even a courtyard fountain where ensemble leads Campbell Scott and Bridget Fonda hang out, mirroring Friends’ splashy opening credits. Plus, both casts of attractively witty and romance-seeking Gen-X-ers are all resolutely and homogenously white.

But looking back through Crowe’s filmography reveals telling influences of their own. The film, intermittently framed by characters speaking their clever thoughts directly to camera, calls up Woody Allen (complete with Hannah and Her Sisters-style interstitial chapter titles). And his 1999 collaboration with a humorously wary and cantankerous Billy Wilder on the career retrospective book Conversations With Billy Wilder, the writer-director cemented a career-long obsession with Wilder’s ever-present, often far more successful search for the perfectly bittersweet line of comic dialogue.

Here, Crowe’s main mouthpiece is Scott’s Steve, a mid-level government employee whose professional drive centers on creating a Seattle gridlock-alleviating “supertrain” — and who also heads out each night to hear the nascent grunge scene’s finest at the city’s hippest clubs. Singles’ soundtrack was ultimately the mammoth success that Singles itself was not, with Crowe’s lifelong pursuit of music scene legitimacy and film soundtrack playability providing a prescient glimpse into the Seattle sound that would take over the nation later that year. After sending his commuter rail proposal up the chain of command, Steve’s called “a realist dreamer” by his impressed immediate boss, a signpost to Singles’ overall vibe of young professionals who work within the system but can still make time to dance to live Alice in Chains.

Later, after a breakup with his on-and-off love interest Linda (Kyra Sedgwick), she wryly tells Steve, “You always say the perfect thing” — another trait that Crowe’s script lays on the engaging Scott, an interesting actor then at the crest of his mainstream rom-com charisma. In Crowe’s films, that quest for the perfect, Wilder-style killer line has curdled over the years. (The cloyingly clever mush of Aloha and Elizabethtown are prime examples, but there’s plenty of eye-roll-worthy speechifying as far back as Jerry Maguire.) Steve here emerges as Crowe’s ideal romantic, perturbed by failed romance but still prone to the sort of grand gestures and poetically self-serving pronouncements that have marked Crowe’s male protagonists. “If I had a personal conversation with God, I would ask him to create this girl,” Steve beams about Linda, to the requisite admiration of his friends.

Luckily for Singles, Scott, like Say Anything’s John Cusack, brings enough natural charm to offset scenes where Steve, attempting to win over the accidentally pregnant Linda with a proposal, pronounces, “Someone who really cares about you must scare you to death.” Sedgwick — never more appealing as battle-hardened environmentalist Linda — is repeatedly charmed by Steve’s oft-presumptuous wooing, as are viewers conditioned to accept that borderline paternalistic romanticism is okay as long as it arrives with a good turn of phrase.

Watch the Trailer for Cameron Crowe’s ‘Singles’ 

Singles’ other major drawing card is a gamine young Fonda as coffeehouse waitress and lapsed architecture student Janet, who’s segued from a past romance with next door neighbor Steve to a swoony, partially reciprocated infatuation with downstairs neighbor Cliff Poncier. Played by a remarkably assured and goofy Matt Dillon as the also-ran grunge frontman of wannabe Mudhoney rival Citizen Dick, Cliff can barely keep his attention on the adoring Janet in favor of his adoring groupies and Citizen Dick’s fraught battle for Seattle scene legitimacy. “We’re huge in Belgium and in Italy!,” he proclaims, attempting to rally his stoner bandmates (including Eddie Vedder and Jeff Ament, right before forming Pearl Jam), Cliff’s pitch-perfect grasper’s cluelessness delivered with just enough genuine desire to be comically affecting.

Singles tries to build out from its core of protagonists, but the ensemble approach never quite comes together. Other residents of the impeccably quirky apartment complex include Jim True (a decade before tracing one of television’s most compellingly unlikely redemption arcs as The Wire’s Roland Pryzbylewski) as hipster maitre d’ David Bailey. With a beret and a soul patch, the character’s hazy claim of living life “like a French movie” is never fleshed out by Crowe, hinting that several subplots were jettisoned along the way. Sheila Kelley’s Debbie is perhaps the most overtly Friends-esque of the group, her foray into then-trendy video dating playing out with a decidedly deflating sitcom vibe. (In a cameo, director Tim Burton accepts a bribe to direct her ultimately silly and pretentious video, a dating service employee’s breathless pronouncement that he’s the next Martin Scorsese an in-joke that only becomes less accurate with time.)

The film’s shaggy structure ultimately latches onto Steve and Linda’s story, with Janet and Cliff’s more knockabout relationship coming in a respectable second. In addition to a pregnancy scare, Scott and Sedgwick’s on-and-off couple contends with a car crash, a resulting miscarriage, a monthlong ocean separation (while Sedgwick studies the lingering effects of the 1989 Exxon Alaska oil spill), and, in Crowe’s clumsiest roadblock to their inevitable reconciliation, Sedgwick’s tape-devouring answering machine. For Crowe, Steve’s drunken late night phone call (from the graffiti-strewn phone booth of a club where Soundgarden is playing “Birth Ritual”) is Singles’ mission statement, a bleary but still cleverly constructed grand romantic gesture where the heartbroken Steve blurts an impassioned, “You! Belong! With! Me!” while angry clubgoers attempt to batter down the door. Like Lloyd Dobler with his boom box, this is Steve as crushed but indefatigable romantic, hurling his exposed heart at a woman and expecting her to take it in and nurture it.

Sedgwick’s Linda does just that, naturally, with a long-delayed visit to the apartment where a disheveled Steve wallows in empty pizza boxes and misery. (His idealistic passion project is slapped down by Tom Skerritt’s cameoing Seattle mayor, heaping another disillusionment on Steve’s already aching shoulders.) “I was just nowhere near your neighborhood,” Linda bashfully announces, her own cleverness merely an echo of the line Steve first employed to first win his way into her apartment. Meanwhile, Janet’s journey to win over the forthrightly noncommittal Cliff takes the form of a proposed boob job. When she’s talked out of the unnecessary cosmetic surgery by none other than her own plastic surgeon (a winning Bill Pullman, pulling off a Scott-like sleight-of-hand by making his subsequent pass at Janet less creepy than it should be), Fonda makes Janet’s sprightly self-actualization a lightweight but worthwhile arc of empowerment. That she winds up back with a repentant Cliff (after he finally remembers to say “Bless you” after she sneezes in the elevator), is the sort of feel-good ending that never quite feels right, but Fonda and Dillon are both so engaged and appealing that we’re conditioned by that point to let it slide.

Back to the Friends comparison: Singles, for all the efforts of its talented cast, is gentrified romantic drama. Crowe’s dedication to showcasing his Seattle locale (he’d fallen in love with both it and Seattle native rock legend Nancy Wilson) and its music scene make Singles feel lived-in, even as its attractive, self-sufficient young cast moves through it more like tourists. (Steve’s oft-mentioned obsession with departed SuperSonics star Xavier McDaniel results in an obtrusive but humorous mid-coitus McDaniel cameo.)

Like its influential soundtrack — including a fine score and two excellent songs from the post-Replacements Paul Westerberg — Singles functions as a sincerely assembled time capsule of a time and place, even if the film’s staying power hasn’t been as indelible.