Marketplace All-in-One What’s money between friends 😟😖😫
Mar 19, 2026
Alison Leiby, stand-up comedian and former TV writer, and Josh Gondelman, comedian and observational writer, trade candid stories about money in friendships. They riff on Venmo culture, wedding and bachelorette costs, saying no to pricey plans, when to refer someone for a job, gift expectations, and who pays for accidental damage. Funny, relatable, and practical takes on awkward financial moments between friends.
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How Josh And Alison Became Close Through Standup
- Josh Gondelman and Alison Leiby became friends through small stand-up shows and open mics after Josh moved to New York in 2011.
- They talk daily, met frequently for a year to work on a writing project, and sometimes go two weeks without seeing each other in person.
Responding To Frequent Small Venmo Requests
- If a new friend group Venmo-requests small items, assume it's their norm or a budgeting practice and either roll with it or bring it up casually.
- Ask for clarity or say you prefer reciprocal, informal paybacks if frequent requests feel awkward.
Small Payments Can Signal Hidden Financial Stress
- Small, immediate money requests can reflect hidden financial constraints or anxiety that friends may not disclose.
- People sometimes prefer knowing the math is squared away to soothe budgeting stress even if they still join group activities.