Sideways

My thoughts

I first saw it back in high school but didn’t understand much at the time—only watched it because others said it was good. This time, it felt more enjoyable. I invited Nami to watch because it’s about wine, and we had a serious conversation about wine. The protagonist seemed like a nerdy loser, while Jack was a flirty, sociable guy—I still don’t get how they’re best friends. The ending felt hopeful. Overall, I liked it; it was sweet and charming.

Summary (full spoilers)

• Miles, a depressed, divorced writer and wine lover, and his friend Jack, a soon-to-be-married actor, set off on a weeklong trip through California’s wine country.
• Miles hopes for quiet wine, food, and reflection; Jack wants one last fling before settling down.
• They meet Stephanie (a wine pourer) and Maya (a waitress). Jack pursues Stephanie without revealing his engagement; Miles and Maya connect more meaningfully over wine and life.
• Miles accidentally reveals Jack’s engagement to Maya, causing anger and betrayal. [3])
• Stephanie learns Jack is engaged and violently assaults him. Jack spirals, losing his wallet (with the wedding rings) and entangling Miles in a risky retrieval attempt.
• At Jack’s wedding, Miles encounters his ex-wife, now remarried and pregnant. Disillusioned, he leaves quietly.
• Alone, Miles drinks his prized 1961 Château Cheval Blanc from a Styrofoam cup. Maya leaves him a voicemail praising his manuscript and inviting him over. The film ends with Miles driving back and knocking on her door—open to hope, but uncertain resolution.