Ask a Matchmaker

Dating burnout, dating app fatigue, and lack of motivation to go out are becoming the MAIN problems in modern dating, and Matchmaker Maria breaks down exactly why! We're joined this week by comedian Rachel Williams for a Hotline episode that tackles how a "frictionless" lifestyle filled with apps, delivery, and convenience is making dating feel harder than ever. A 32-year-old caller shares her str...

What if friendship is the real key to finding love? This week, Maria sits down with author and connection coach  Shari Leid , who shares the unbelievable story of being found as a baby in a cardboard box and how that shaped her mission to fight loneliness and seek connection. After a recent divorce and cross-country move, Shari reveals how traveling to all 50 states to share meals with strangers l...

It's a Hotline episode 👏 This week, Matchmaker Maria is joined by CEO of Agape Escapes, Amalia Kalogridakis, for a rapid-fire dating advice episode! They cover: money, friendship, and age gap relationships! They discuss whether $100,000 in credit card debt is a dating dealbreaker, how to rebuild your social life when your boyfriend is your only friend, and if a 39-year-old woman dating a 24-year-...

Matchmaker Maria is joined by TODAY.com senior editor Elena Nicolaou for a powerful conversation on miscarriage, partner support, and the reality of navigating women's healthcare. Elena shares the emotional story of finding out she was pregnant with quadruplets, miscarring, and then having to face a $41,000 medical bill after surgery! They also get into what grief looks like inside a marriage, how...

Limerence, obsessive dating thoughts, and why you can't stop checking your phone? Matchmaker Maria sits down with journalist and author Amanda McCracken , whose writing on relationships has been published in the New York Times, Guardian, and Vogue, to break down the psychology of intense romantic infatuation. Amanda shares how she dated over 100 men, struggled with "anchormen" from her past, and r...

Comedian Chloe Radcliffe  joins Matchmaker Maria for a dating advice hotline episode about modern dating, relationships, dating apps, and finding a serious partner. They help a listener figure out how to work with an ex-boyfriend who betrayed her but still wants the breakup kept secret at their workplace. Another caller asks how to balance casual dating and having fun at 29 while still wanting to...

JFK Jr. and Carolyn Bessette's relationship, the viral "Alpine Divorce" dating trend, religious values in modern matchmaking, and the viral Hinge baker experiment are all part of today's dating conversation. In this solo episode, Matchmaker Maria reacts to the TikTok trend where partners abandon each other on hikes and explains why selfish behavior in relationships is often a pattern. She also bre...

Did millennial women grow up inside a system designed by powerful men? In this episode, Maria is joined by journalist Ileana Justine to unpack how mall culture, Victoria's Secret, JUICY sweatpants, low-rise jeans, and dress code "fingertip rules" shaped millennial body image, and how the Jeffrey Epstein era exposed who held the power behind those brands. They break down the male gaze vs. the femal...

Hard conversations in relationships, attachment styles, anxious vs avoidant dynamics, and emotional disconnection are at the center of this week's Ask A Matchmaker. Matchmaker Maria sits down with therapist and author Colette Fehr  to explain why couples fight about small things like Duolingo, texting back, or Valentine's Day flowers when the real issue is feeling unheard or unimportant. They brea...

Dating across cultures, first-generation identity, and family pressure in relationships take center stage on this episode with Matchmaker Maria and licensed clinical psychologist Dr. Rosette Elghossain to unpack how immigrant upbringing, enmeshment, and early family dynamics shape adult dating choices. They dive into navigating parental expectations, setting emotional boundaries, dating outside yo...

Dating apps, AI matchmaking, modern love, Valentine's Day dating, and real relationship tips collide in this solo episode as Matchmaker Maria breaks down the rise of AI matchmakers and what they actually get wrong about human connection. From chatbot dating coaches to algorithm-driven matches, Maria explores why faster swiping doesn't equal better relationships, and why real matchmaking has always...

It's a fun hotline episode with Sex and the City impressions, dating long distance advice, and knowing that marriage isn't for you! Matchmaker Maria is joined by hilarious stand up comedian  Anna Roisman  for a hotline episode packed with dating advice, love, and real-life dilemmas. Maria even gets to hear Anna's spot-on Steve from Sex and the City impersonation as they break down relationships, c...

Women menopause and perimenopause take center stage as Matchmaker Maria sits down with therapist and women's health advocate Lauren Tetenbaum , author of Millennial Menopause , to talk about what's really happening in the body and why most of us were never taught this. They break down the truth that menopause is technically one day, while perimenopause can last years and affect mood, sleep, libido...

Divorce, emotional healing, lonliness in divorce, and dating after divorce are explored as therapist Oona Metz joins Matchmaker Maria for an honest conversation about why divorce is not a bad word. This episode covers the 5 top reasons for divorce, why the opposite of love is not hate, why you are not alone in your divorce, and how divorce can be a powerful life transition instead of a failure. Oo...

In this episode of Ask a Matchmaker , Matchmaker Maria dives into the world of ethical non-monogamy with guests Victoria Joseph and her husband Ryan, professional ENM matchmakers who are married and also swing. Together, they break down what ENM actually means, including the differences between open relationships, swinging, and polyamory, and explain how ethical non-monogamy differs from consensua...

In this Hotline episode, Matchmaker Maria is joined by author and late-bloomer expert Allora Dannon to deliver no-nonsense dating advice rooted in clarity, confidence, and tough love! They tackle real listener dilemmas, starting with a woman struggling to finally break up and whether going no contact is the only way to heal. They revisit an update from the woman who discovered her boyfriend on a d...

In this special year-end episode of Ask A Matchmaker , Matchmaker Maria looks back on the biggest dating lessons of 2025 and what they mean for intentional dating in 2026. Featuring standout guests like Vera Papisova, Joyelle Nicole Johnson, Weezy W.T.F, Jared Freid, Kaneez Surka, Erika Ettin, Tara Cannistraci, and more, Matchmaker Maria breaks down conversations on politics, polyamory, attachment...

What happens to connection when we put our phones away? Matchmaker Maria sits down with Randy Ginsberg, founder of Kanso , to unpack phubbing (phone snubbing), modern dating burnout, and why being truly present has become one of the most underrated relationship skills. Together, they explore how intentional, phone-free spaces create deeper conversations, stronger chemistry, and real opportunities...

Comedian and writer Caitlin Peluffo returns to Ask a Matchmaker for an honest catch-up with matchmaker Maria after a major relationship shake-up. Caitlin opens up about calling off a long engagement, what it taught her about passion, independence, and settling, and why starting over in her 30s has been unexpectedly empowering! Together, they dive into dating while living alone, long-distance relat...

This week, Maria talks with author and speaker Emily Goodson about her new book  Dating Disability: 15 Stories of Dealing with the BS and Building Confidence . Emily shares her experiences dating with a disability and how working with an intimacy coach helped her break patterns of shame and self-protection. They discuss visible and invisible disabilities, the social barriers disabled people face,...

This week, Maria talks with creator and political strategist Tega Orhorhoro bout growing up in a Nigerian household, dealing with constant pressure to "reach the next milestone," and learning to date on her own terms. Tega shares how reading Ask a Matchmaker changed how she approaches apps and why small updates to her profile completely shifted who she matches with. They also talk about Tega's ris...

Maria sits down with journalist and podcast host Nayeema Raza for a sharp, funny, deeply insightful conversation about the rise of AI dating companions, why posting your partner now feels embarrassing, and how Zohran Mamdani's love story gives real hope for dating in NYC! Maria and Nayeema talk about the rise of AI dating companions and how many young adults are turning to emotional relationships...

Maria sits down with NYU professor and AI pioneer Vasant Dhar for a grounded, eye-opening conversation about how artificial intelligence is reshaping our lives! They break down the rise of AI companions, the risks of sharing personal information with chatbots, and why these systems can feel human while still lacking empathy. Maria and Professor Dhar explore how modern AI "knows a little about ever...

Matchmaker Maria sits down with therapist Rebecca Marcus to explore how millennial women can break toxic dating patterns and build meaningful, healthy relationships. They discuss attachment styles, nervous system regulation, and how urgency and anxiety can shape who we choose and why. Rebecca shares how slowing down, building self-trust, and practicing emotional awareness can transform your dating...

Matchmaker Maria dives deep into why modern dating feels harder than ever, and why it's not your fault! Maria explores how convenience culture has stripped away connection and offers practical, no-nonsense ways to rebuild your "dating muscles." From reclaiming third places to embracing real-world friction, Maria shares how to create opportunities for love instead of waiting for them. If you're rea...