Pretty Padded Room

Illustrated by Mary Galloway. My boss is pretty blatant about playing favorites — and I'm not one of them. She's especially chummy with two

Illustrated by Anna Sudit. My friend and roommate has recently turned into a mean drunk. Most days of the week, she’s great to be around, and I love

Illustrated by Anna Sudit. My boyfriend and I graduated last year, and I felt lucky that I landed a great job. Meanwhile, my boyfriend told me he got into

Illustrated by Madelyn Somers. Ever since my sister and her girlfriend broke up last year, she’s been super depressed. I know it was hard on her, but

Illustrated by Tania Lili. My girlfriend’s parents are very involved in her life. She’s an only child, so I get it, but she talks to them every

I made the mistake of accepting a friend request from the receptionist at work. She’s always very talkative early in the morning and can never take a

Photographed by Ruby Yeh. My new roommate (ahem, life partner) is super messy — I'm talking leaving bowls of food and beers out messy. On all ot

My boyfriend announced he wants to have a threesome…with a guy. We’ve talked about threesomes before when talking dirty, but I always assumed

Illustrated by Sydney Hass. A friend asked me to be a bridesmaid in her wedding but we’re not that close, and I don’t have the money for all th

I just had sex for the first time with a guy I’ve been going out with for a while. It was...well, let’s just say it was inexplicably, catastrophically

Illustrated by Mary Schafrath. I’m working at a start-up that I really believed in when it first launched. One year later, it’s the same bureau

Illustrated by Sydney Hass. I'm black, and most of my friends are white. It's been like that my whole life, and there's never been any major

Illustrated by Ammiel Mendoza. A few months ago, I was promoted at work, and now I'm making more money than my boyfriend. It wasn't an issue unti

I just turned 32, and I'm pretty sure I've never had an orgasm. I enjoy sex, but it never has that "wow" thing for me that it seems to for everyone else. I

My husband and I double date with another couple often. She’s super flirtatious in a way that makes me uncomfortable. Last time we hung out, she was aski

I lent money to a friend about three months ago and she still hasn’t paid me back. She has a job and it wasn’t a huge amount so I’m not sure why she

One of my best friends recently told me I have “selfish tendencies.” She gave me a few examples and I actually understood where she was coming from and

I’m a newlywed and newly pregnant and should be over the moon, but I’m miserable. I’ve been so sick since about three weeks in that I’ve become a n