What Jackie Oshry has said about Dear Toasters advice segment

Jackie Oshry advised a listener to ask directly for gifts she wants rather than expecting a partner to guess.

“No, that's on being direct. Like, nobody's a mind reader. If you want something, just ask for it”

The Toast: Girls Trip to Brisborne: Tuesday, June 30th, 2026 (Jun 30, 2026) · Listen from 1:04:10

Jackie Oshry advised a new mother to get her botched highlights fixed regardless of her sister-in-law's feelings.

“I'm sorry, you don't have to have ugly hair to protect someone's feelings”

The Toast: Girls Trip to Brisborne: Tuesday, June 30th, 2026 (Jun 30, 2026) · Listen from 1:05:05

Jackie Oshry said she would suspend a mother-in-law's solo time with the child until the unauthorized haircut grows out.

“I would light her up, and I would say you can see her again when her hair grows back out”

The Toast: Girls Trip to Brisborne: Tuesday, June 30th, 2026 (Jun 30, 2026) · Listen from 1:07:37

Jackie Oshry argues that pre-engagement relationship doubts are often resolved by committing and starting a family.

“sometimes some things can be solved when you do decide to commit to somebody and propose and start a life and start a family”

The Toast: Nicolandria Incorporated: Wednesday, May 6th, 2026 (May 6, 2026) · Listen from 1:02:37