Ring, ring! It's 1-800-BRIDESMAID.Author and professional bridesmaid Jen Glantz brings her hit newsletter to life in this judgment-free space for messy wedding, friendship, and relationship dilemmas.This week, Jen is joined by Hilary Sheinbaum, New York City–based journalist and author of The Dry Challenge and Going Dry: A Workbook. Hilary spent years writing about wine, beer, and bar openings across the city—until a silly $100 bet with a friend kicked off a Dry January that completely changed her lif...
Ring, ring! It's 1-800-BRIDESMAID.
Author and professional bridesmaid Jen Glantz brings her hit newsletter to life in this judgment-free space for messy wedding, friendship, and relationship dilemmas.
This week, Jen is joined by Hilary Sheinbaum, New York City–based journalist and author of The Dry Challenge and Going Dry: A Workbook. Hilary spent years writing about wine, beer, and bar openings across the city—until a silly $100 bet with a friend kicked off a Dry January that completely changed her life, her career, and eventually, her wedding.
Together, they talk about everything from the pressure to drink at every wedding event, to what it's actually like to walk down the aisle completely sober, to navigating a social life where alcohol is the default.
But today's listener question takes things to another level.
A bride writes in after discovering that her fiancé has been secretly draining their honeymoon fund—the money gifted by friends and family through their registry—to pay off his credit card debt. He claims it was temporary and "just our money anyway." Now she's questioning everything: the trust, the wedding, and whether she should still walk down the aisle.
Jen and Hilary unpack the red flags around financial infidelity, why money conversations need to happen long before you sign the marriage license, and how to protect yourself when your partner isn't being transparent.
Episode Highlights:
- How a $100 bet turned into a sober lifestyle and a career pivot
- The hidden ways alcohol affects your sleep, mental health, and friendships
- Saying "I do" without saying cheers — what a sober wedding actually looks like
- The growing world of nonalcoholic cocktails and why hosts should offer them
- When a partner hides debt: red flag or dealbreaker?
- Why financial transparency belongs on the table before the wedding venue
- The case for prenups, joint money meetings, and protecting your future
- Using AI as your unofficial second opinion on health, finances, and tough conversation
If you've ever felt pressure to drink at every wedding event, questioned what real financial transparency looks like in a relationship, or wondered whether some secrets are worth calling off a wedding over, this episode is full of honest perspectives and real advice.
This episode is brought to you by Travel by @davidsbridal— plan your honeymoon, getaway, or room block all in one place, with savings up to 30%. Visit davidsbridal.com/travel to get started today.
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