Could My Grandma’s “Cookie Jar” Relationship Theory Be The Answer to Getting More From Men?

It was me, my sister Jilly, and my grandma at the kitchen table—the same one that had seen decades of card games, birthday cakes and family gossip. Jilly was mid-rant about her friend, who had been “seeing” a guy for three months without a single real date.

“She swears she’s in love with him,” Jilly rolled her eyes. “But he’s never once taken her to dinner, never even bought her a drink.”

Grandma chimed in with her signature Brooklyn accent: “Hang on, he’s neva taken her to dinner? What do they do, braid each other’s hair?” 

“I mean, she basically just hangs out at his apartment,” Jilly continued. “Netflix, takeout, maybe he’ll walk her to the corner for coffee in the morning.” 

I clocked the still dumbfounded expression on Grandma’s face. “It’s called a situationship, Gram,” I clarified. “You don’t have the label of ‘boyfriend-girlfriend’... It’s what usually happens when a girl wants more from the guy—like with Jilly’s friend.”

Grandma huffed. “Gimme a break.” Then she held up the ceramic cow-shaped cookie jar beside her. “You see this? Men are just like boys with a cookie jar,” she lifted the lid and popped an Oreo in her mouth. “They can’t resist reaching in for something sweet. And the first time they sneak a cookie, maybe you let it slide. But do that two, three times, and suddenly they’re emptying the jar behind your back. You’ve got nothin’ left for yourself.”

From there, the conversation segued into gossip I can’t divulge. But later that night, I got to thinking: how many cookies do we let slide in dating? And when do those harmless snacks turn into something that leaves you starving?

It doesn’t start with the obvious. It starts small—sometimes so insignificant you barely register it. But over time, the jar starts to empty. Here’s a breakdown of how it plays out (pulling from the typical situationship blueprint): 

• Week 1: He cancels plans last minute. “Work’s crazy,” he texts. You’re annoyed, but hey—life happens. You reschedule.
• Week 2: He texts “wyd” at 11:17 p.m. on a Thursday. You respond. You even go over. You tell yourself it’s spontaneous.
• Week 3: He hasn’t planned a single date, but he’s happy to tag along to things you organize. Concert at Brooklyn Mirage? Cool. Friend’s rooftop party? Sure. He never offers, but he never says no either.
• Week 4: He says, “I’m bad at texting,” and you take that as law. Three-day gaps become standard. You stop expecting the “how was your day?” or “what are you up to this weekend?” texts. 
• Week 5: You start booking dinner reservations. You choose the gift for his niece’s birthday. You remind him to call his landlord and bring cold medicine when he’s sick. He calls you “thoughtful.”
• Week 6: He forgets your presentation is today. Doesn’t ask how it went. But he does send you a TikTok of raccoons fighting over a hotdog.
• Week 7: You finally ask him, “What are we?” He says, “I’m just not great at relationships.” You don’t take it as a hard pass, so you thank him for being honest.
• Week 8: You’re now rationing your own needs like it’s wartime. “Don’t be too sensitive.” “Don’t bring it up again.” “Don’t scare him off.”
• Week 9: You look around and realize: you’re the one refilling the jar while he helps himself whenever he pleases.

This cycle only exists because we let it. Per Grandma, it’s because “Men will get away with as much as you allow them to.” She explains, “If you keep lettin’ ‘em take a cookie, they’ll take a cookie. If they steal one, they’ll always go for another. And another. They don’t stop until the jar is empty—or until you swat their hand away.” In other words, most men aren’t sitting and plotting how to emotionally deplete you. But if you don’t call out the behavior—if you continue to let silent disappointments slide—they’ll assume they’re doing just fine. 

Which brings me to the core disconnect: women are taught that boundaries might scare someone off. We smile. We swallow the annoyance. We tell ourselves it’s too early to say something—or that maybe we’re being dramatic. But men are taught that boundaries don’t exist until someone’s yelling. It’s no wonder that most are shocked when we boil over after months of withholding. To us, “I can’t do this anymore” is the result of all the resentment we’ve pushed down. But to them, it’s the equivalent of swapping the chocolate chip cookies for oatmeal raisin without warning.

So here’s what I’ve learned, both from Grandma and some hard-earned fieldwork: you set the bar for how someone treats you. Not with dramatic ultimatums, but with silence. Every time you bite your tongue instead of naming what’s wrong, you reinforce the behavior. Every time you say “it’s fine” when it’s absolutely not fine, you’re sending the message: go ahead, my lid is open.

Yet, when you speak up, everything shifts. Maybe you tell him, “I hate it when plans are canceled last minute.” Or maybe you say, “It’d be nice to eat dinner outside of your apartment.” In fact, I’ve actually had fun with setting boundaries in my later twenties. Instead of reciting a this is how you make me feel soliloquy, I’ve texted everything from “Take me off your bootycall mailing list” to “You do realize normal civilians eat before 11 pm, yes?” In my experience, adding some bite thins out the herd. You can’t set the wrong boundary with the right guy—and when you say it with confidence? It doesn’t kill chemistry. It creates it.

It all goes back to Grandma’s theory: men will always try to reach into the cookie jar. Maybe they’re wired that way—curiosity, convenience, hunger—it’s in their DNA. But the right guy won’t pout when you swat his hand. He won’t call you crazy for having a lid. He’ll take the redirection, figure out what your favorite cookie is, and ask how you like it served. And for you, naming what you need shouldn’t be a threat—it should be a reset. It shines a light on who’s capable of stepping up for you, and who’s sticking around for easy access. 

Ultimately, sweetness is yours to give. Keep your jar full like Grandma would—and remember: “Just because someone wants a cookie doesn’t mean they’ve earned one.”