Estranged Sibling
Reconnecting with estranged brother
From The Giannis-Knicks Flirtation. Plus, Jeff Passan on Judge Saving the Yankees, More MLB Playoffs, and Life Advice! · · Ringer era
Email 4 in this segment
Haven't spoken in 11 years. He just emailed asking to meet.
From "The Giannis-Knicks Flirtation. Plus, Jeff Passan on Judge Saving the Yankees, More MLB Playoffs, and Life Advice!" · email starts at 01:25:48
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More emails on family
Couple in Texas
Relocating for in-laws
Wife's parents need help. We'd move 1,400 miles and I'd take a 30% pay cut.
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Grandkid
Grandpa gone wild (dating much younger)
Grandpa is 74. New girlfriend is 38. Family is split. Do I say something?
From Chiefs, Bucs, and Drake Maye Are Big Winners. Plus, Danny Kanell on Penn State’s Overreaction, Indiana’s Biggest Win, and the SEC’s Problem. — Oct 13, 2025
Divorced Dad
Holidays after divorce
First Christmas split. Kids 9 and 12. Ex wants Christmas Eve every year forever.
From Chiefs, Bucs, and Drake Maye Are Big Winners. Plus, Danny Kanell on Penn State’s Overreaction, Indiana’s Biggest Win, and the SEC’s Problem. — Oct 13, 2025
Thirty-Two
Moving back home at 32
Bay Area rent broke me. Parents have room. Career suicide or smart play?
From Chiefs, Bucs, and Drake Maye Are Big Winners. Plus, Danny Kanell on Penn State’s Overreaction, Indiana’s Biggest Win, and the SEC’s Problem. — Oct 13, 2025
Younger Sibling
Older brother always one-ups me
Every life update, my brother has done it bigger. How do I handle holidays?
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New Husband
In-law conflict ahead of holidays
Mother-in-law refuses to acknowledge my career change. Wife won't confront her.
From The Giannis-Knicks Flirtation. Plus, Jeff Passan on Judge Saving the Yankees, More MLB Playoffs, and Life Advice! — Oct 8, 2025