Dear So and So

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?