GLD 580 - What Do You Deserve in a Relationship?

Ever thought you deserved a little morr than you were getting? What can we fairly expect from someone we love? Marcus and Lily from Secrets of a Sugar Daddy stop by to weigh in on six listeners’ opions on the merits Are these reasonable needs, or does calling something deserved turn a relationship into a transaction? The conversation gets especially candid when Lily shares how a sugar dating arrangement grew into real love. A deep dive on chemistry, appreciation, the trouble with keeping score - and a first date that ended as soon as the meal did.

Sometimes the conversations you almost don't have turn out to be the ones you never forget.Eight years ago, Brian sat down with Jillian Michaels expecting an intimidating conversation with one of the most recognizable - and opinionated - fitness personalities in the world. Instead, she became his favorite guest in the history of The Great Love Debate. So we're going back into the vault for a conversation that might be even more interesting today than it was in 2018. Jillian gets candid about confidence, body image, getting older, relationships, sexuality, communication, food, fitness, sleep, stress, and learning to stop trying to please everybody. She explains why hitting 40 finally brought her to a place of accepting her body - and why what we call a "midlife crisis" might actually be the moment you realize the way you've been living simply isn't sustainable anymore.She and Brian also get into why life gets unnecessarily complicated, the importance of keeping things simple, what strong communication really looks like when you're angry or overwhelmed, and why having more ways to communicate hasn't necessarily made us any better at it. A classic Great Love Debate conversation about health, love, confidence, balance, and discovering that the people who intimidate us most might have the most to teach us.

Are we actually too busy for love...or have we just gotten lazy about finding it? Brian the lovely, lively, and newly engaged Crystal Carroll for a wildly wide-ranging GLD about what happens when technology starts doing the romantic heavy lifting.We have dating apps to find the person, AI to write the texts, matchmakers to make the introductions, social media to investigate them, and Uber to make sure we don't even have to endure the ride home together. We have more ways to communicate than ever before - so why does it seem like we're getting worse at actually connecting? Brian and Crystal debate why men aren't approaching women anymore, whether modern dating has become too safe and convenient, why nobody seems willing to define the relationship, and whether outsourcing rejection is also outsourcing the very vulnerability required to fall in love. Plus: dating after divorce, why some people stay in marriages long after they know they're over, love bombing vs. actually loving someone, whether social media is a dating necessity or a giant red flag, the trouble with lying about your height - and Crystal's controversial rule that a guy might have to wait eight to ten dates for a kiss. Brian, unsurprisingly, has some thoughts!

What is the State of the Date in 2026?  Brian takes stock of where men, women, attraction, pursuit, sex, flirting, and relationships stand right now - and why he believes we’ve somehow managed to take a lot of the fun out of the thing that’s supposed to be fantastic. Have men lost their motivation to pursue women? Have we demonized male desire to the point that guys have stopped trying? Have women become so independent and guarded that they’ve forgotten the power of being pursued? Is it time to "just be horny, baby?"  Our full annual report delivered up hot and fresh. Plus, how Dolly Parton held the dating secret sauce!

You want them to notice you, but what makes them remember you? "What's Wrong With Me?" host Cayla Cook returns - and this time she and Brian are trying to figure out what’s wrong with all of us. A funny, revealing, and occasionally uncomfortable look at what we bring into dating before the other person even gets a chance to screw it up. From childhood baggage and emotional walls to independence, vulnerability, gratitude, and the things we refuse to admit about ourselves, sometimes the biggest obstacle to finding love isn’t them. It’s us.

What happens when bad communication meets dating apps, fake dogs, surprise proposals, loyalty tests, and a rent-free apartment owned by your girlfriend’s ex? Brian is joined by Renee Scherzer, author of Lightwork: Life Beyond the Ladder and host of The LightWork Podcast, for the return of one of The Great Love Debate’s favorite traditions - The Basket of Bad Decisions!Brian and Renee tackle a six-pack of listener-submitted relationship disasters and decide who made the bad decision - and whether there’s any coming back from it. From a boyfriend running a secret Hinge sting operation, to a man borrowing his sister’s golden retriever to impress a date, to a couple who accidentally panic-proposed to each other, nothing is off limits. Plus, Brian and Renee confess a few questionable romantic decisions of their own. Sometimes the worst decisions make the best stories - and occasionally, they even teach you something. 

Maybe it really is just you! Brian welcomes "The Scottsdale Matchmaker" Cat Cantrill for a candid, funny, and occasionally uncomfortable look at what’s really happening in today’s dating world. Why have men become so hesitant to approach women? Are dating apps actually worse for men? Do successful singles have unrealistic expectations? And at what point does having “high standards” become a convenient excuse for never giving anyone a real chance? All this and much, much more - including the best first date story...ever?

Are your “type” and your ex’s labels getting in the way of finding love?Brian takes aim at two of the biggest obstacles in modern dating: labels and type. From casually diagnosing every bad ex as a “narcissist” to ruling out potential partners because they’re the wrong height, personality, political affiliation - or even the wrong LaCroix flavor - Brian argues that we’ve become far too good at finding reasons to keep people out.Instead of asking, “What’s wrong with them?” Brian challenges us to ask a harder question: What part did I play in the outcome? He explains why “He was a narcissist” and “She was crazy” are often lazy explanations for relationships that simply didn’t work, why being “not my type” is one of the most damaging phrases in dating, and why the person you least expect could ultimately be the person who changes everything.

Sometimes the best love stories don't begin in your twenties - they begin after you've stopped looking. Brian welcomes "Golden Sex Podcast" host Diane Marie Carty for one of the most candid, entertaining, and surprisingly inspiring conversations ever on The Great Love Debate.After spending 14 years focused on family, caregiving, and simply surviving life, Diane had all but written off romance. Then came an unexpected meeting, an unforgettable first date, and a relationship that completely changed how she views love, intimacy, aging, and happiness. The conversation explores:Why so many people unknowingly take themselves out of the dating gameLife after divorce and caregivingRediscovering confidence after 50The surprising realities of dating later in lifeWhy chemistry has no age limitHow one chance encounter can change everythingIt's funny, vulnerable, provocative—and a reminder that your next great love story could be waiting just around the corner.

Is the rise of the independent woman responsible for a decrease in dating success? "Charisma Quotient" host Kimmy Seltzer returns to unpack why so many accomplished women struggle to find lasting love despite having everything else figured out. From flirting and feminine energy to dating confidence and modern relationship dynamics, this episode challenges conventional dating advice while offering practical strategies for creating genuine connection. Whether you're newly single, divorced, or simply tired of dating apps, Kimmy and Brian will change the way you think about attraction and relationships.