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 Bonnie Winston — celebrity matchmaker, relationship expert, and founder of Bonnie Winston Matchmaker. Bonnie has spent years helping people outsource their love lives, rethink what they’re really looking for, and open themselves up to matches they might have completely overlooked on a dating app. Together, Jen and Bonnie unpack what modern dating really looks like when the apps stop feeling fun and start feeling exhausting. Why are so many people burned out from dating? Are your “non-negotiables” actually helping you find love, or quietly blocking you from it? What happens when your dream partner looks nothing like the checklist in your head? And how do you know when you need to keep dating — or take a break and come back to yourself? But today’s listener question hits one of the most vulnerable dating fears of all: what if nobody wants to date me? A woman writes in saying she’s 34, has been single for three years, has been to therapy, used the apps, said yes to setups, gone to events, and been on 60 dates. Some went somewhere, one lasted four months, and another ended when she found out he was dating someone else the entire time. Meanwhile, her friends are married, having kids, and moving forward — while she’s going to weddings alone, leaving early, and wondering what is wrong with her. Jen and Bonnie break down what dating burnout really does to your confidence, why “I’ve done everything” might not mean you’re dating with the right intention, and why redefining what you actually want can change the way you show up. Bonnie explains why this listener may not need to disappear from dating for six months, but she does need to stop saying yes without clarity and start advocating for the kind of love she actually wants. And then comes the twist: the listener eventually deleted the apps, stopped tracking dates, took a pottery class, went on a solo trip to Portugal, started going to bed early, and slowly became someone she liked again. Nine months later, she met someone at a friend’s birthday dinner — and they’ve now been together for a year and a half. Episode Highlights: Why hiring a matchmaker is like outsourcing your love life The difference between what people think they want and who they actually fall in love with Why your dating checklist might be blocking the right person What Bonnie tells clients who are too focused on height, education, location, or status Why dating apps can make people overly judgmental How to meet people “in the wild” without making it weird Why saying hello, smiling, and being present still matter The first-date mistakes that can kill chemistry fast Why you should not trauma dump on a first date If you’ve ever wondered why dating feels so hard, questioned whether your standards are helping or hurting you, gone on too many first dates that went nowhere, or felt like everyone else is finding love except you, this episode is full of honest, funny, and deeply human advice about dating burnout, confidence, matchmaking, and what it really means to stay open to love.
