I don't necessarily like wearing lipstick; I just think it's

Host: The apartment was dimly lit, filled with the soft hum of an old turntable spinning a warped record that crackled like memory. The walls were cluttered with old posters — Bowie, Velvet Underground, a half-torn flyer for a band that never quite made it. A single lamp cast amber light across the chaos: guitars, empty bottles, paint-smeared Polaroids, and an ashtray overflowing with small, poetic failures.

Host: Jack sat on the couch, strumming a guitar out of tune, his hair messy, his jeans torn just enough to suggest both rebellion and routine. Jeeny leaned against the window, a cigarette balanced between her fingers, the city stretching out below like a restless constellation. On the coffee table between them, a smear of dark lipstick gleamed under the lamp — the only deliberate color in the room.

Host: On a page torn from a music magazine, the quote sat scrawled in the margin, a kind of accidental philosophy.

“I don’t necessarily like wearing lipstick; I just think it’s funny to do. I think the darker the better, but it’s whatever my girlfriend Kiera has in her purse.”
— Mac DeMarco

Jeeny: “You’d probably agree with him,” she said, her eyes glinting with mischief. “You’ve always believed irony is the only honest emotion left.”

Jack: “Irony’s just self-defense,” he said, plucking a string. “The armor of our generation. You act like you don’t care so no one can prove you do.”

Jeeny: “Maybe. Or maybe irony’s just another way of saying we miss sincerity but we don’t trust it anymore.”

Host: The record skipped slightly, a small imperfection that somehow made the song sound more alive. Jeeny walked over, took the tube of lipstick from the table, and rolled it open. The color was a deep, almost bruised purple — the kind that dared to be noticed.

Jeeny: “You ever wonder why things like this — lipstick, eyeliner, glitter — make people so uncomfortable when they see them on a man?”

Jack: “Because it blurs the line. And people need lines. They need to know where everything belongs.”

Jeeny: “And what happens when something doesn’t?”

Jack: “They laugh. Or they hate it. Usually both.”

Jeeny: “Maybe that’s why Mac calls it funny. He’s not mocking it — he’s defusing the threat. Humor’s how you survive being misunderstood.”

Jack: “You sound like you’ve rehearsed that line.”

Jeeny: “I’ve lived it.”

Host: The city noise below — the sound of engines, sirens, distant laughter — rose faintly through the cracked window. It mingled with the hiss of the vinyl, the soft sigh of night air. Jeeny sat beside him now, her eyes catching the light, the lipstick still in her hand.

Jack: “You really think it’s just a joke to him? Wearing lipstick?”

Jeeny: “No. I think it’s permission. To play. To blur. To exist somewhere between ‘should’ and ‘why not.’”

Jack: “Play’s dangerous. People think the world’s too serious for that.”

Jeeny: “And yet the world’s dying from a lack of it.”

Host: She leaned forward and handed him the lipstick. He looked at it, skeptical but curious — like someone staring at a magic trick he half wanted to believe in.

Jeeny: “Go on,” she said.

Jack: “What, you want me to make a statement?”

Jeeny: “No,” she said. “I want you to stop needing one.”

Host: He hesitated, then — almost in defiance of himself — twisted open the tube. The smell was faintly sweet, absurdly innocent. He smeared the dark color across his mouth in one unsteady motion. It was uneven, imperfect, raw.

Jeeny smiled.

Jeeny: “There,” she said. “Now you’re beautiful and ridiculous at the same time.”

Jack: “Feels wrong.”

Jeeny: “It’s supposed to.”

Jack: “Why?”

Jeeny: “Because beauty always starts with discomfort. You have to break something first — expectation, ego, fear.”

Host: The record ended. The silence that followed was heavy, not awkward — more like a moment of awareness that neither of them could quite escape.

Jack: “You think that’s what Mac was getting at?” he asked finally. “That the act doesn’t matter — just the freedom behind it?”

Jeeny: “Exactly. Lipstick’s not rebellion. It’s play. And play is freedom disguised as humor.”

Jack: “So when he says it’s ‘funny,’ he means it’s sacred.”

Jeeny: “Sacred in the way silliness is sacred. In the way laughter is a rebellion against shame.”

Host: He looked at his reflection in the window — the city lights shimmering over his faintly smudged mouth. He looked both foolish and human, and for the first time that night, utterly unguarded.

Jack: “You know,” he said, “it’s strange — how something so small can feel like confession.”

Jeeny: “That’s the power of art,” she said. “Even when it’s borrowed from your girlfriend’s purse.”

Jack: “You think it’s easier for artists to live like that — without borders?”

Jeeny: “Easier? No. But they understand that identity isn’t a prison; it’s a playground.”

Host: The lamp flickered slightly, casting their shadows long against the wall. For a moment, the two of them looked like reflections caught between worlds — half-serious, half-satirical, all alive.

Jack: “You think people ever stop needing permission to be who they are?”

Jeeny: “Only when they realize no one else ever had it either.”

Jack: “That’s grim.”

Jeeny: “That’s freedom.”

Host: The turntable spun to a stop with a final click. Outside, the wind shifted, carrying the faint scent of rain and possibility.

Jeeny reached out and wiped a small streak of lipstick from the corner of his mouth, her thumb leaving a dark smudge on her skin.

Jeeny: “See?” she whispered. “Art. Temporary. Messy. True.”

Jack: “And funny.”

Jeeny: “Always funny.”

Host: The city lights flickered through the window, dancing across the lipstick tube, the guitar, the faces of two people who no longer cared where irony ended and honesty began.

Host: And as the record’s silence filled the room, Mac DeMarco’s words seemed to hum through the air like a soft laugh — both absurd and profound:

“I don’t necessarily like wearing lipstick; I just think it’s funny to do. I think the darker the better, but it’s whatever my girlfriend Kiera has in her purse.”

Host: Because sometimes humor is the purest form of truth —
the kind that doesn’t preach or defend,
the kind that dares to exist in the space
between mockery and meaning.

Host: And in that absurd, beautiful blur,
Jack and Jeeny sat —
two souls painted in contradiction,
proof that the darker the color,
the truer the laughter,
and the freer the heart that wears it.