Neil Turns 40, Ali's $400 Babysitter, Matching Family Outfits, and My Son Stuck His Finger In The Pencil Sharpener

Neil Padover celebrates the big 4-0 with matching family outfits (this year with custom shirts featuring his face), a fancy dinner, and a trip to the Whitney, only to cap the week by getting kicked out of the Brooklyn Museum during a chaotic field trip. Ali Khan (Cheap Eats, Spring Baking Championship) shares his own parenting pain: a babysitter who charged him $400 for an overnight stay while she slept. The guys get into the cost of childcare, Brooklyn au pairs, Austin tech bros, and what happens when your kid thinks his fingers are literal pencils. Plus, aging gracefully (or not), the guys trade SAT scores, and the bittersweet countdown to your kid's graduation.