1-800-Bridesmaid

The Reason You're Not Getting a Second Date (And It's Not What You Think)

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 Erin Davis — professional wing woman, dating strategist, and VIP matchmaker at Three Day Rule. Erin has built a career around the unconventional: she goes out with her clients to bars and singles events (sporting a $9 cubic zirconia ring from Burlington Coat Factory so no one mistakes her for the girlfriend), runs mock dates, and coaches singles through everything from first-date small talk to ending a 14-month situationship. Together, they unpack the dating rules that actually work in 2026 — from the three-month "over the hump" mark to why ChatGPT should never write your texts, why "potential" is the most dangerous word in dating, and how to know when you're wasting time versus building something real. But today's listener question hits a nerve almost everyone has felt. A woman writes in after 14 months in a situationship. They text every day. They've taken two trips together. He's met her sister; she's met his friends. But every time she asks what they are, he says he's "not in the right place." She's tried to walk away twice — and both times, he's pulled her back within 48 hours. She doesn't recognize herself anymore. Erin delivers a word-for-word script for the cold-turkey breakup, explains the Pavlov-style psychology of why he keeps coming back, and breaks down why rejection isn't the worst thing that can happen in dating — lost time is. Episode Highlights: What a professional wing woman actually does (and why she wears a fake engagement ring) The "ghost winging" technique that makes shy clients irresistible without saying a word Why three months is the real "over the hump" mark in any new relationship The case against using ChatGPT for dating — and what to use instead Voice notes vs. texting: the new rules of communication Why "potential" is the most dangerous word in dating How to leave a situationship for good (Erin's exact script) The Pavlov theory of why he keeps coming back after you've left Going deep on a first date — when to do it and how not to spiral The dating advice that actually works after 35 If you've ever wondered whether you're settling, whether he'll ever change, or whether you should stay another six months "just to be sure" — this episode is full of honest, no-BS dating advice from someone whose entire job is helping people stop wasting time and find the real thing.

Her Fiancé Secretly Drained Their Honeymoon Fund… Should She Still Marry Him?

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 [https://www.davidsbridal.com/travel] to get started today.

My Maid of Honor Is Dating My Ex — And Wants to Bring Him to My Wedding

Ring, ring! It's 1-800-BRIDESMAID. Author and professional bridesmaid Jen Glantz brings her hit newsletter to life in this judgment-free zone for all your messy, real wedding, love, and friendship dilemmas—plus expert advice to help sort them out. In this episode of 1-800-BRIDESMAID, host Jen Glantz sits down with Brooklyn hairstylist and former ballerina Nathan Ayon to talk about wedding culture, the pressure around marriage, and what actually makes a wedding meaningful. Nathan has spent years behind the salon chair — one of the few places where people share their most honest, unfiltered thoughts about relationships, love, and life. His unique perspective on what people really feel about weddings might surprise you. Then, Jen and Nathan tackle a real listener dilemma: a bride finds out her maid of honor has started dating her ex-boyfriend — and now wants to bring him as her plus one to the wedding. They unpack the complicated line between loyalty and romance, and what it truly means to show up for a friend on one of the most important days of her life. In this episode: - What hairstylists hear in the salon that no one else does - The real pressure people feel around marriage and weddings - MOH vs. bride: where does loyalty end and personal life begin? - How to handle a maid of honor who's dating your ex - Setting boundaries with your wedding party without blowing up a friendship - What actually makes a wedding memorable — and what doesn't matter at all This episode is brought to you by Travel by  @davidsbridal  [https://studio.youtube.com/channel/UCs964ZJCyPn0HWbxaEda_Sw] Plan your honeymoon, getaway, or room block all in one place, with savings up to 30%. Visit https://www.davidsbridal.com/travel [https://www.davidsbridal.com/travel] to get started today.

She Found a Secret Bridesmaids Group Chat About Her…

Ring, ring! It's 1-800-BRIDESMAID. Author and professional bridesmaid Jen Glantz brings her hit newsletter to life in this judgment-free zone for all your messy, real wedding, love, and friendship dilemmas—plus expert advice to help sort them out. This week, Jen is joined by Tasha Dwhaj, a social media personality, producer, and reality TV contestant who once found herself in one of the most unexpected wedding roles imaginable: a bridesmaid for a bride she had never met. Together, they dive into the complicated world of friendships, weddings, and the expectations we place on relationships. Tasha opens up about why she didn’t believe in marriage for years, what changed her perspective, and why she believes couples shouldn’t feel pressured to follow society’s timeline. But today’s listener question brings the drama. A bride writes in after discovering that her bridesmaids had a secret group chat without her—filled with comments about how stressful she had become and jokes about her appearance during wedding planning. Now she’s left wondering: should she confront them, remove them from the wedding party, or pretend she never saw the messages? Jen and Tasha break down the emotional reality behind wedding planning, friendship loyalty, and what it really means to support someone during one of the most stressful times of their life. Episode Highlights: • What it’s like to be a “stand-in bridesmaid” at a stranger’s wedding • Why wedding stress can change friendships overnight • The truth about bridesmaids gossip and group chat drama • Why Tasha didn’t believe in marriage until her 30s • The pressure couples face to follow the traditional timeline • How to decide if a friendship is worth saving • What to do when the people in your wedding party stop acting like your friends If you’ve ever questioned your friendships, dealt with wedding party drama, or wondered what people are saying in the group chat without you—this episode is full of honesty, perspective, and advice you’ll wish you had sooner.

I Found Out My Best Friend Got Married on Instagram

Ring, ring! It's 1-800-BRIDESMAID. Author and pro bridesmaid Jen Glantz brings her hit newsletter to life in this judgment-free zone for all your messy, real wedding, love, and friendship dilemmas—plus expert advice to help sort them out. This week, Jen is joined by Alyssa Pettinato, a NYC-based event planner and host of Miss Judged, who has seen it all—from chaotic wedding days to complicated relationships—and isn’t afraid to say the quiet part out loud. Together, they get into the reality behind weddings and relationships: why getting married doesn’t fix anything, what really happens when couples ignore red flags, and how weddings can bring underlying issues to the surface. But today’s listener question hits close to home. A woman writes in after discovering her best friend of 16 years secretly got married—and she found out on Instagram. No invite. No heads up. No explanation. Now she’s left wondering: is this still a friendship worth holding onto… or is this the moment everything changes? Episode Highlights: • Why weddings can amplify relationship doubts and hidden issues • The pressure to get married—and why it’s not always the right move • Alyssa’s own broken engagement and what she learned from it • The biggest red flags to watch for before saying “yes” • Why friendships can hurt more than romantic relationships • How to handle being excluded from a major life moment • When it’s time to have the hard conversation… or walk away If you’ve ever questioned a relationship, felt left out by a friend, or wondered if you’re forcing something that doesn’t feel right—this episode is full of honesty, perspective, and the kind of advice you actually need.