This Is Uncomfortable

What’s money between friends 😟😖😫

Mar 19, 2026
Alison Leiby, stand-up comedian and writer (Broad City, The Marvelous Mrs. Maisel), and Josh Gondelman, comedian and writer, trade stories about money and friendship. They cover Venmo culture and nickel-and-dime drama. They tackle wedding and bachelorette budget stress. They debate damaged-property payback and setting boundaries around pricey gifts and referrals.
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ADVICE

Match The Group Or Name Your Preference

  • If a new friend group splits small costs via Venmo, adapt or gently communicate your preference for reciprocity.
  • Reema suggests either roll with their system, casually bring it up, or say you prefer a today-for-you-tomorrow-for-me style.
INSIGHT

Small Venmo Requests Can Signal Budgeting Needs

  • People send small Venmo requests partly to soothe financial anxiety or because they actually need exact accounting.
  • Alison and Josh note that requesting small amounts can be a budgeting strategy, not just pettiness.
ADVICE

Say No To Unsustainable Bachelorette Spending

  • Be candid with friends about wedding and bachelorette affordability; set a clear lower budget or offer low-cost ways to celebrate.
  • Alison and Josh recommend saying your limit (eg X dollars), doing logistics work, or suggesting smaller celebrations.
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