I want to be a cool mom.

Host: The suburban evening hummed with the low drone of distant lawnmowers and the scent of grilled meat drifting through the breeze. The sun sagged into a burnt orange haze, painting the rows of identical houses with a strange, cinematic melancholy.

In the driveway of one such house, Jack leaned against his car, a faint smirk curling under his five-o’clock shadow, watching Jeeny unpack a box marked “Teen Stuff — Keep.”

A faint pop song bled through an open window, and from somewhere inside, the laughter of a child — thin, bright, and too brief — sliced through the air like a memory.

Jeeny: “Do you remember what Tori Spelling once said? ‘I want to be a cool mom.’”

Jack: (half-laughing) “Yeah, I think I saw that on some magazine cover back in the 2000s. Glitter fonts, pink headlines, the works.”

Jeeny: “It’s funny, right? But there’s something underneath it. Every mom I know — hell, every parent — wants to be understood, not just obeyed. ‘Cool’ isn’t really about fashion. It’s about connection.”

Jack: “Or about approval. Let’s not sugarcoat it. ‘Cool’ means liked. Parents are supposed to guide their kids, not audition for them.”

Host: The light shifted, falling across Jack’s angular face, catching the faint trace of a scar along his chin. Jeeny straightened up, brushing dust from her jeans, her brown eyes warm but defiant.

Jeeny: “You sound like my father. He used to say, ‘I’m not your friend, I’m your parent.’ And guess what? He never understood me. I followed his rules, sure — but I never talked to him. Ever. That’s not parenting; that’s governance.”

Jack: “And yet, you turned out fine.”

Jeeny: “Did I? Or did I just learn to hide who I was to avoid his disapproval?”

Host: The crickets began to chirp, soft but insistent, weaving their song into the thick heat of the evening. A dog barked down the street, and the world felt both still and trembling — as if something unsaid hovered between them.

Jack: “Look, Jeeny, kids don’t need their parents to be cool. They need boundaries. They need someone to tell them no. If you start caring about being liked, you lose the moral high ground.”

Jeeny: “The moral high ground? That’s not parenting, that’s power. Maybe being a ‘cool mom’ isn’t about being liked — it’s about being approachable. So your kid doesn’t have to lie to you to be seen.”

Jack: “You can’t have both. Respect and popularity don’t live in the same house.”

Jeeny: “No — but love and understanding do.”

Host: A streetlight flickered on, buzzing faintly, casting a halo over the driveway. The air thickened with the smell of hot asphalt and honeysuckle.

Jack: “I get it, you want to be the kind of mom who your kid can talk to about anything. Drugs, heartbreak, failure, all of it. But you can’t force that kind of trust. Trying too hard just makes it worse. The more you try to be cool, the more awkward you look.”

Jeeny: (laughs softly) “You sound like you’ve lived that.”

Jack: “My mother tried. After my dad left, she dyed her hair blue, started using slang she didn’t understand, bought me concert tickets to bands she hated. I didn’t talk to her for a year. It wasn’t the hair, or the slang — it was the desperation. Kids can smell that a mile away.”

Jeeny: “Then maybe the problem wasn’t her trying — it was her fear. She didn’t want to lose you, Jack.”

Jack: “And in trying not to lose me, she did.”

Host: The pause that followed felt like a held breath. Jeeny’s eyes softened, her expression shifting from defiance to understanding. The distant hum of the highway filled the gap, a long, low echo of time passing.

Jeeny: “You know, it’s easy to mock the idea of being a ‘cool mom’ when you’re not the one living with a teenager who slams doors instead of speaking. Sometimes, being cool just means being safe — a place where your kid’s chaos won’t get them punished.”

Jack: “And what happens when your kindness turns into permission? When cool becomes careless?”

Jeeny: “Then you course-correct. But at least your kid knows you’re human. Isn’t that the whole point? To raise humans, not obedient shadows?”

Jack: “You’re romanticizing it. Parenting isn’t therapy. It’s war — fought on the battlefield of discipline and love.”

Jeeny: “Then I’d rather fight it with humor and honesty than with fear and rules.”

Host: The night deepened. Fireflies blinked lazily above the grass, their tiny lights like the remnants of forgotten dreams.

Jack: “You want to be a cool mom. I get that. But maybe the ‘cool’ part doesn’t matter. Maybe it’s about being real. Someone who doesn’t pretend to have all the answers.”

Jeeny: “Exactly. Cool isn’t a look — it’s a presence. It’s the trust you build when your kid sees you not as a statue, but as a story still being written.”

Jack: “So, you think vulnerability is the new authority?”

Jeeny: “Maybe it always was.”

Host: A car drove by, its headlights washing across their faces — his stoic, hers earnest, both haunted by the ghosts of childhood and parenthood. The light passed, leaving them in a dim stillness that felt almost sacred.

Jack: “When I was twelve, I got suspended for fighting. My mom came to pick me up. She didn’t yell. Didn’t say a word in the car. Just drove me to a bookstore. Bought me a copy of The Catcher in the Rye. Said, ‘Maybe this will make sense to you someday.’ That was the coolest thing she ever did.”

Jeeny: “Why?”

Jack: “Because she saw me — not as a mistake, but as a person trying to understand the world. That’s cool. Not pretending, not forcing, just… seeing.”

Jeeny: (softly) “So maybe she was a cool mom after all.”

Jack: (smiles) “Yeah. Maybe she was.”

Host: The wind shifted. The smell of rain lingered faintly on the air, like an old memory returning. Jeeny smiled, placing the box down gently, as though setting down the weight of an entire generation’s expectations.

Jeeny: “You know what I think, Jack? Every parent just wants one thing — not to be feared or idolized, but to be remembered kindly.”

Jack: “And maybe that’s what cool really means.”

Jeeny: “Yeah. Not trendy. Just kind.”

Host: The porch light flickered as they both looked toward the house, where a small shadow — a child’s silhouette — darted across the window, laughing.

Jack: “Guess your kid’s still awake.”

Jeeny: “Good. Maybe she’ll see I’m out here trying to be cool.”

Jack: (grinning) “You’re getting there.”

Jeeny: “No. I’m just being here.”

Host: And with that, the laughter inside grew louder, spilling through the open window — a reminder that the true measure of cool isn’t in being perfect, but in being present.

The night sighed, the stars blinked awake, and for a fleeting moment, the world — messy, loving, real — felt exactly as it should: beautifully unfinished.