“How much is your rent and how can you afford this place?!”
This has probably happened to you before. You meet someone cool and normal. And then one day they invite you over to their apartment and you discover they are seriously rich. They live in a luxury building with a doorman, and have a one bedroom apartment all to themselves. You’re left standing there clutching your coupon to Chipotle with your mouth wide open. “But they’re so normal. They wear Urban Outfitters and drank PBR with me at that party in Bushwick once.” The rich live among us sometimes in secret. Not everyone feels the need to be grandiose about their wealth. They just want to blend in! When you find yourself surprised by someone’s lavish apartment, do NOT ask, “How much do you pay for rent…if you don’t mind me asking?” General rule of thumb: If you have to precede a question with, “if you don’t mind me asking”, chances are you shouldn’t be posing the question in the first place. “How can you afford this place?” is not only a dumb question (how else do you think someone under the age of 30 can afford a plush apartment?), it’s totally rude! The only suitable response to that illegal question is, “You haven’t heard? Money grows on trees now! There’s a great money tree on 12th street that I pick at the end of the month for rent. It’s amazing.” Money is touchy, babe. And people who are on the DL about their big finances usually don’t want to talk about it. Respect.
“How far along are you?”
I thought this question was only asked in bad romantic comedies, but no, it happens IRL too. One day I accompanied my friend to Saks Fifth Avenue in San Francisco so she could buy an $8000 dollar bottle of perfume, and the sales lady totally asked how far along she was in her pregnancy. I was shocked but also not really. The sales people at high-end department stores are usually old ladies who have blown through their trust fund and are very bitter about having to sell things they used to be able to afford. So they end up saying really fucked up passive-agressive shit to customers. The thing is that my friend didn’t even look pregnant. I mean, she’s Real Women Have Curves because she’s Spanish, but in no way does she look like she could be with child. Anyway, the question totally took the wind out of my friend’s shopping sails. The perfume counter lady ended up getting really embarrassed and threw in 200 samples of perfume to smooth things over. In fact, I’m wearing one of the scents today! But for future reference, you should never assume anyone is pregnant ever. I don’t care if it looks like someone’s about to pop out a child through their vagina in a grocery store, it might just be a tumor in their stomach.
“Are you gay?”
It actually stuns me that people ask this question like it’s asking, “How are you?” If you meet someone and they haven’t revealed their sexuality via a comment about the same sex or something similar, you can’t just be like, “Are you gay?” because they might be in the closet or even worse, actually straight (they’re never actually straight though). It’s best to just ask their friend because they’ll know the 411 better than anyone else. In some cases, they may be like, “Yeah. He’s totally a homo but he hasn’t come out. We all know though.” and you have to accept it. Don’t try to ask in some backwards ass way either. If someone is suspected of being gay, they’re hyper sensitive to it and aware of what you’re doing when you spend ten minutes gushing about what a babe Ryan Gosling is. They will spend those minutes sweating bullets and eyeing the door so don’t do it.
“Has anyone ever told you that you look like *insert ugly celebrity here*?”
All celebrities are not created equal. I learned that the hard way when I told my best friend she reminded me of Hilary Duff. Unbeknownst to me, Hilary Duff is widely perceived as a hideous gargoyle with poor fashion sense—not a beautiful movie star. Oops. People have different ideas of beauty. Bearing a striking resemblance to Jessica Simpson may cause someone to jump for joy while making another throw up their dinner. Personally, I think if someone’s a celebrity, they have to at least be attractive to somebody. A truly ugly person would never be in the public eye. And if by some fluke accident they are, their ugliness becomes a part of their celebrity (See Susan Boyle). So think before you ask because a compliment could be taken as an insult.
How old are you?
This question is usually fine for anyone under the age of thirty, but it gets a bit touchy after that. Why? Maybe it’s because we live in an ageist society and people always want to look a decade younger. This is nothing new. What is interesting, however, is the stigma that comes with being young. A 21-year-old will be having a great conversation with someone who’s 29, and suddenly feel shy when asked to reveal their age. I don’t know, dude. When is someone ever the right age? 25? 
