Is it a red flag if your boyfriend resents that you make more money? NYC matchmaker Anna Morgenstern joins 1-800 Bridesmaid to explain how modern matchmaking works, why your dating “non-negotiables” might be keeping you single, and why prenups are the new normal. Then they take on two listener letters: a woman who out-earns her boyfriend 3 to 1, and a woman whose matchmaker set her up with her friend’s ex.

In this episode: How matchmaking actually works today Why height requirements usually aren’t real deal breakers Instagram matchmaking and the new singles ads AI in dating, and the profile photo mistakes to avoid Listener letter: “I make 3x more than my boyfriend and he resents me” Why prenups can lead to stronger marriages Listener letter: “My matchmaker set me up with my friend’s ex” Do soulmates exist?

🔔 Subscribe to 1-800 Bridesmaid for new episodes every other week — real callers, real wedding and friendship dilemmas, real advice.

Got a wedding dilemma or relationship question? Submit your story at 1800Bridesmaid.com.

What happens when your first engagement ends six months before the wedding and your second fiancé calls it off three weeks out? Entrepreneur and marketing consultant Hope Alcocer, founder of Wonder Woman Media, joins 1-800 Bridesmaid to share her story of two called-off engagements, a fresh start in New York City, and the Hinge match she turned down before he became her husband.

In this episode:

• Hope's first engagement at 22, and why she called it off
• How her second fiancé ended things three weeks before the wedding
• Buying a one-way ticket and starting over in NYC
• Working through panic attacks on the subway, and finding therapy
• The highs and lows of dating in New York
• Meeting her husband on Hinge while recovering from long COVID
• The Father's Day text that brought them back together
• Listener letter: "My fiancé proposed to his ex and never told me"
• Listener letter: "I'm on my second engagement and want to call it off"
• Cold feet, trusting your intuition, and how your cycle affects big decisions

🔔 Subscribe to 1-800 Bridesmaid for new episodes every other week — real callers, real wedding and friendship dilemmas, real advice.

Got a wedding dilemma or relationship question? Submit your story at 1800Bridesmaid.com.

In this episode of 1-800 Bridesmaid, host Jen Glantz sits down with NYC psychotherapist Jessica Zweig to unpack the messiest parts of modern dating, friendship, and relationships — and answer two real caller dilemmas live on the show.

Jessica works with clients in their 20s, 30s, and 40s on dating, anxiety, trauma, and relationship patterns, and she's bringing that expertise straight to your bridesmaid problems. Jen and Jessica cover:

- Why influencer "dating rules" (the 3-day text rule, who should chase whom) do more harm than good - When — and how — to tell someone you're dating about anxiety, depression, or mental health struggles - How to support a friend going through something you can't relate to - Caller #1: A friend ghosted her for two years, then sent a wedding invite expecting instant forgiveness — should she go? - Caller #2: Her therapist told her to break up with her boyfriend, and he's demanding she stop seeing that therapist. Who's right? - Why weddings can't fix broken friendships, and what to do when someone expects yours to - Breaking toxic relationship cycles and why change is so much harder than wanting change

Whether you're navigating a complicated friendship before a wedding, wondering if you should go to an event for someone you've drifted from, or just love hearing real advice for real bridesmaid problems, this episode delivers no-nonsense, therapist-backed guidance.

🔔 Subscribe to 1-800 Bridesmaid for new episodes every week — real callers, real wedding and friendship dilemmas, real advice.

Got a wedding dilemma or relationship question? Submit your story at https://www.1800Bridesmaid.com.