How do I get my books back from a former friend and ex-lover—is the appropriate channel through his new girlfriend? Am I being rude or difficult if I tell people on a conference call that I can't hear them? If I REALLY want to pay for dinner, should I start a Venmo war with my dining partner? Or should I just run after our server and pull her ponytail until she runs my card? Plus: Alyssa teaches us how to divine someone's dream sandwich.

How do I let the rest of my party know I don't intend to share my dessert? Can I abandon my wife in line and use TSA PreCheck when we travel as a couple? Who should initiate flirting in a bartender-patron situation? And can I be sure I'm actually crushing—what if all I really want is a free glass of wine?

Do I have to come clean to the person I want to marry that on our first date, I let her believe I was someone she’d already slept with: my twin brother? Someone embarrassed me in 1974, will I ever get past this? How do I hold onto my low-FOMO after lockdown? Plus, we settle “but you told me to hurry!” speeding ticket disputes for everyone involved, once and for all.

Is it "unphysical abuse" and a "disservice to his feelings" to name my cat Richard? How do I tell my mother-in-law that my five-year-old doesn't need haute couture? Should I attend the wedding of two people I don't recognize and am not even sure I know? Plus: Is Alyssa telling the truth, can I reset my sweat?

Celebrating fifty episodes and one entire year of Dear So and So, we hosted a live anniversary show on Zoom and you came through and this is IT! Featuring special guests Kristen Carlisle, Bizzy Hemphill, and Mona Blumstein.

(16:50) It's a zebra-print bikini top. (47:16) The question polled was: Do Steph and/or Alyssa give you a lot of unsolicited advice, or do they channel it toward the show?

I took a new job, I found out it's a cult, what's my next move? What's more unprofessional: covering your cubicle in positive affirmations, or rolling your eyes at them so hard you can see the back of your head? Plus, what on earth is an Apology Dinner and is one happening right now at your local PF Chang's?

How do you tell someone to stop lighting things on fire in the office bathroom? Is it possible to make new friends on a cruise ship if you're unemployed? Sometimes my coworker completely transforms her appearance on her lunch break and I'm worried it's unprofessional, but is it, in fact, awesome?

My nanny makes wacky cakes that my children love, but I think they're amateurish. Can I put a stop to this? Did I tank office morale when I flung a sandwich at my frosty boss? Plus, is there a point at which minimalism becomes maximalism again?