This Past Weekend w/ Theo Von

Snapshot · This Past Weekend w/ Theo Von

#664 - Crooners Welcome

Explore episode Jun 21, 2026

Where this was said

Voicemail: Jealousy and a Girlfriend's Past (Michael from Utah)

At 33:10 · chapter starts 28:30

Michael from Utah has been with his girlfriend for eight months and loves her, but is tormented by jealousy over her past — things she did before they met that don't align with where he's been. He's struggling to forgive and love unconditionally. Theo's response is candid and self-implicating: he's been that guy. He held old girlfriends accountable for things they couldn't change, used the past as 'a little card' that gave him permission to be upset, and kept one foot out of the relationship at all times. He reframes the question: what if instead of holding her past against her, you became the person who ensures she never has to operate in uncertain environments again? What if you were brave enough to love her the way she should be loved? The analogy of a calendar throwing an old bad Wednesday back at you is both absurd and precise — and Theo's final image of standing alone with 'a bunch of old hurdles' is one of the sharpest lines in the episode.

Society & Culture
Jealousy Is Just One Foot Out the Door

#664 - Crooners Welcome · Jun 21, 2026 Society & Culture

Holding a partner's past against them isn't really about their history — it's about keeping an escape route open. Theo admits he did it himself, and names it for what it is: fear of full commitment dressed up as moral standards.

Society & Culture
Advice for a Fatherless Father Raising Three Boys

#664 - Crooners Welcome · Jun 21, 2026 Society & Culture

A caller raising three boys without ever having a father figure asked for guidance. Theo's answer — write down what you didn't get and you'll find your roadmap — comes wrapped in his own confession about growing up under 250% judgment.

Similar snapshots

Society & Culture
Private adoption costs $40,000–$70,000

Tortilla Face · Aug 10, 2026

Private domestic infant and international adoptions typically cost $40,000 to $70,000, while foster care adoption is the most affordable route at $0 to $2,000.

Society & Culture
7th of 10 children

"Robby Hoffman" · Aug 10, 2026

Robby Hoffman is the 7th of 10 children raised in a Hasidic household in Montreal, where the family was poor and comedy was a survival mechanism.

Society & Culture
No concept of 'too soon'

"Robby Hoffman" · Aug 10, 2026

Robby's Hasidic community had no concept of 'too soon' in comedy — if it was funny, you threw it, and if you bombed, your sibling told you immediately.