Plus One (2019)
If 'When Harry Met Sally' got a modern, millennial makeover, it would look a lot like 'Plus One'. Long-time college friends Ben (Jack Quaid) and Alice (Maya Erskine) decide to be each other's platonic dates for a seemingly endless summer of weddings.
The setup is pure rom-com, but the execution feels fresh and surprisingly real. Their banter is sharp, profane, and laugh-out-loud funny, masking a vulnerability that fans of Nora Ephron's writing will recognize. The film brilliantly captures the chaos of being single when everyone around you is pairing up, but its true heart lies in the slow-burn realization that the person you've been complaining to all along might just be the one you've been looking for.
Sleeping with Other People (2015)
This film takes the central question of 'When Harry Met Sally'—can men and women be just friends?—and pushes it to its raunchy, modern extreme. After losing their virginity to each other in a one-night stand in college, Lainey (Alison Brie) and Jake (Jason Sudeikis) reconnect years later at a sex addicts meeting. Realizing they're both serial cheaters who sabotage their own relationships, they forge a platonic friendship built on radical honesty, establishing a safe word for when things get too tense. The dialogue is relentlessly witty and refreshingly frank about love and sex, but underneath the humor is a genuinely heartfelt story about two flawed people trying to become better for each other.
Enough Said (2013)
From director Nicole Holofcener, who many consider an heir to Nora Ephron, comes a romantic comedy for grown-ups. Julia Louis-Dreyfus stars as Eva, a divorced masseuse who is dreading her daughter leaving for college. She meets Albert (a wonderfully warm James Gandolfini), another divorcee in the same boat, and they begin a sweet, funny, and realistic courtship. The problem? Eva’s new client and friend, Marianne (Catherine Keener), is constantly complaining about her awful ex-husband… who turns out to be Albert. The film skips the flashy romance for something more grounded and mature, focusing on the insecurities and baggage that come with finding love in middle age. The dialogue is smart, the performances are incredibly touching, and it has the same intelligent, heartfelt core that makes Ephron's films so beloved.
Before Sunrise (1995)
While it's not a traditional 'friends-to-lovers' story, 'Before Sunrise' is essential viewing for anyone who loves the conversations in 'When Harry Met Sally'. The entire film consists of two strangers, Jesse (Ethan Hawke) and Céline (Julie Delpy), meeting on a train and deciding to spend one magical night walking and talking through Vienna before they part ways. The movie is almost entirely dialogue, but it’s utterly captivating. They discuss life, love, death, and everything in between, their connection deepening with every shared thought and vulnerability. It captures that rare, electric feeling of meeting someone you can talk to for hours, where the intellectual and emotional intimacy is the main event. It’s the romance of a truly great conversation, spun into a classic film.
Always Be My Maybe (2019)
This Netflix hit perfectly captures the 'what if' feeling of reconnecting with a childhood friend. Sasha (Ali Wong) and Marcus (Randall Park) were inseparable as kids in San Francisco until an awkward teenage encounter led to a major falling out. Sixteen years later, Sasha is a celebrity chef and Marcus is a hometown musician, and their worlds collide when she returns to open a new restaurant. The film is a hilarious and heartwarming exploration of the friends-to-lovers trope, grounded by the undeniable chemistry between its leads. It beautifully explores how people grow apart and whether they can find their way back to each other, all while being genuinely funny and featuring a now-legendary cameo from Keanu Reeves. It’s a love letter to friendship, food, and second chances.
