Pillow Fort - Episode 22 - Losing Your Phone & Being Too Nice

Aimee just cannot understand how Roo free-boobs it so much. The no-bra, sweatshirt life is simply too hot for her to handle. This naturally leads to a discussion on the struggles of bra shopping and finding something that actually fits.

Roo recaps her cruise—specifically, all the endless food and restaurants on board. This inspires Aimee’s grand idea: all of society should be run like a cruise line. You pay a fee, and you get food, a place to sleep, and medical care. Roo, however, immediately pokes holes in the plan. The reason cruises work? No kids. The second you add kids into the mix, the whole party—and society itself—falls apart.

Speaking of cruise chaos, Roo lost her phone in the Bahamas, and her location is still pinging from there. Aimee is convinced this means real Roo never actually returned, and she’s now talking to alternate reality Roo. But Roo reassures her—she’s free-boobing, so it must be the real her.

Roo also talks about the nightmare of losing a phone while traveling, dealing with multi-factor authentication when you don’t have a device, and the frustration of banks flagging or closing accounts when you’re out of town. This reminds Aimee of when she used to drink a lot and would lose her phone on a monthly basis.

Aimee lets Roo know that she missed her while she was gone, but Roo clams up—because she physically cannot accept love. Which leads perfectly into Aimee’s topic: Being Too Nice to People. Aimee has always defaulted to being nice, but people constantly mistake it for romantic interest. She just wants to be kind! But in stand-up comedy—especially in Florida—niceness is often seen as a weakness. She struggles to find a middle ground between being genuinely herself and not getting taken advantage of.

Roo solves the mystery of why men always think you’re hitting on them if you’re nice: because no one is nice to men.Generations of men were raised by men who were mean to them. Women, at least, are socialized to be somewhat nice to each other, but men are taught to be tough and detached.

This leads to a deep dive into how people react to kindness. If Aimee is too nice, people shut down. If Roo receives a compliment, she instinctively downplays it because she was taught not to be arrogant. Women in general are often conditioned to shrink themselves—don’t be too confident, too boastful, too anything. On the flip side, people also assume that if someone is overly nice, they must want something.

Aimee, being naturally nice, is drawn to people who have no problem telling others to f** off*. But both she and Roo agree—if you’re in a city, you cannot be too nice. You have to assert dominance, avoid eye contact, and keep yourself safe. It’s like the contrast between the cutthroat world of stand-up comedy versus the kind, nurturing world of improv. It all comes down to balance—finding the people you can truly be yourself with versus navigating the world outside.

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