Libsyn Directory

Should You Go On A Second Date Without Chemistry? ft Amy Chan

Release Date: 06/16/2026

How Long Should a First Date Actually Be? ft Lauren Davis

Ask a Matchmaker

Comedian, joins for a fun conversation about red flags, marathon first dates, dating app lies, and why a 2 hr date might be better than spending 10hrs together! They discuss the best first date activities, from walking and museums to bowling, and answer a listener question about dating in Spain at 62. It's a fun episode you don't want to miss! Check out Lauren's travel themed digital show 👉 ♥️JOIN MARIA’S COMMUNITY + SUBMIT A QUESTION ❓ Ready to date with intention? 💌 Visit Maria’s website or submit your own dating question: 👉 ✈️ TRAVEL WITH...

Are Smartphones Contributing to the Birth Rate Crisis? ft Christine Emba

Ask a Matchmaker

Could your smartphone be affecting your dating life and even the birth rate? talks to writer and cultural critic about research linking smartphones to declining fertility and how scrolling may be replacing the time people once spent meeting, flirting, and connecting. They also get into porn, AI, dating apps, and algorithms that are changing how men and women see relationships. Follow Christine’s work in The New York Times and subscribe to her for more of her writing and ideas. ♥️JOIN MARIA’S COMMUNITY + SUBMIT A QUESTION ❓ Ready to date with intention? 💌 Join...

Can Grief Show You You're With the Wrong Person? ft. Gus Constantellis

Ask a Matchmaker

Comedian joins to talk about turning his late mother's recipes into a cookbook that became a heartfelt memoir about grief, family, and finding joy again. They dive into how losing a parent changed the way Gus looked at love, why his mom's advice to "come up for air" ended a five year relationship, and what it was like watching his dad start dating again just weeks after her passing. Plus, they answer whether it's a red flag if your date can't cook, debate a fourth date that skips dinner, and reveal the Greek meal that might just make someone fall in love! Check out his book here 👉 ...

The 4 Dating Personality Types That Predict Compatibility

Ask a Matchmaker

breaks down what compatibility really means and why finding the right partner has nothing to do with shared hobbies or a Myers-Briggs label. She explains the four dating personalities, why your lifestyle is really about how you value your time and money, and the questions every good dater should be asking. Plus, hear the surprising story of the woman who thought she wanted an adventurous partner until one personality test changed everything and led her to her husband. If you've ever wondered why your relationships keep missing the mark, this episode is your roadmap. Check out this test today!...

Why Feeling "Too Much" Is Actually a Strength ft Alison Leiby

Ask a Matchmaker

Comedian and author joins to talk about her new essay collection and why every version of ourselves deserves a seat at the table. They discuss different identities, only-child life, surviving a near death experience, chronic back pain, stand up comedy, and how those experiences shape dating and relationships. Plus, the two answer a listener who feels like she's lost herself after ignoring red flags in a relationship and wants to learn how to trust herself again. If you've ever wondered who you are outside of dating, this episode is for you! ♥️JOIN MARIA’S COMMUNITY +...

Should One Bad Joke End a Date? ft Jourdian Fisher

Ask a Matchmaker

Comedian joins for a hilarious hotline episode about dating, love, and learning when not to "fix" your partner's problems. Go check out his comedy special, , today!! They break down whether weed is a real deal breaker, if one bad joke should end a relationship, and what it really means when someone says they're "going through something." Plus, Jordan shares how Bumble led him to love, why he used to fear commitment, and the relationship lesson every boyfriend needs to hear: sometimes "Wow, that sucks" is enough. ♥️JOIN MARIA’S COMMUNITY + SUBMIT A...

Practical Optimism Can Save Your Dating Life ft Dr. Sue Varma

Ask a Matchmaker

Psychiatrist and couples therapist joins to explain why optimism isn't something you're born with, it's a skill you can build. They break down the difference between healthy realism and catastrophizing, why overthinking keeps people single, and how "maximizers" sabotage dating by chasing endless options. Plus, they answer a listener question about a boyfriend who's afraid to take the next step toward marriage and whether it's your job to fix your partner's fears. If dating has started to feel hopeless, this episode shares practical ways to change your mindset without falling into toxic...

Jared Freid Explains the Different Types of SINGLE

Ask a Matchmaker

is back on Ask a Matchmaker to talk about his new book, , and why most dating advice completely misses the average guy's perspective. Jared and Maria dive into the "types of singles," why family setups may be better than dating apps, the difference between "main street" and "alleyway" dating, and whether social media is making dating harder than it needs to be. They also debate TikTok dating rules, the taxi cab theory, Snapchat requests, Uber expectations, and why "if he wanted to, he would" might be terrible advice. Plus, Jared plays a rapid-fire round of "Walking Red Flag or Overthinking...

Should You Go On A Second Date Without Chemistry? ft Amy Chan

Ask a Matchmaker

, author of joins to break down why so many people feel burned out by dating and what they're getting wrong! They discuss Amy’s "dating funnel," why a lack of chemistry on a first date shouldn't always be a dealbreaker, and how doomscrolling, TikTok, and dopamine overload may be sabotaging your love life. Plus, a listener from Miami asks how to stay hopeful after disappointing dates, and Amy shares her favorite pre-date ritual to create better connections. If you're tired of dating apps, chasing sparks, or wondering why first dates never go anywhere, this episode is for you. ...

Is Dating Your Friend's Ex Ever Okay? A Summer House Debate with Chrissy Rutherford

Ask a Matchmaker

sits down with writer and mental health advocate to discuss the Summer House drama behind her essay, From dating a friend's ex to the complicated realities of interracial dating, Chrissy explains why Ciara's experience struck such a nerve with so many black women. They dive into fetishization, friendship loyalty, codependent relationships, and the emotional impact of feeling desired but not chosen. support the show, support the sponsors! Go to and use promo code MATCHMAKER at checkout for $35 off. Minimum purchase may apply. ♥️JOIN MARIA’S...

More Episodes

Amy Chan, author of On Single, joins Matchmaker Maria to break down why so many people feel burned out by dating and what they're getting wrong! They discuss Amy’s "dating funnel," why a lack of chemistry on a first date shouldn't always be a dealbreaker, and how doomscrolling, TikTok, and dopamine overload may be sabotaging your love life. Plus, a listener from Miami asks how to stay hopeful after disappointing dates, and Amy shares her favorite pre-date ritual to create better connections. If you're tired of dating apps, chasing sparks, or wondering why first dates never go anywhere, this episode is for you.

♥️JOIN MARIA’S COMMUNITY + SUBMIT A QUESTION ❓

Ready to date with intention?

💌 Join Maria’s Roundtable community or submit your own dating question:
👉 https://www.matchmakermaria.com/askaquestion
Use promo code ROUNDTABLE50 for $50 off