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Dating is sometimes just a string of mistakes and learning experiences.  We’ve all had our ups and downs – from figuring out how to flirt to navigating new relationships to learning how to read subtle cues. It’s sometimes trial and error, but who says it all to be sooo serious? What if, instead of internalizing our setbacks, we took a moment to laugh at them? Laughter is the best medicine, after all.

That’s why our guest this week is Lane Moore, host of the comedy stage show Tinder Live. She’ll be joining us to talk about her new book “You’re Not the Only One Effing Up: Breaking the Endless Cycle of Dating Mistakes.” 

Later on, for our “Dear Damona” segment, we’ll answer this question: People often say boring equals healthy. But are there ever times this just isn’t true?

All right, pull up a chair and get ready, lovers. As they say, love don’t cost a thing – but our advice is priceless!

DATING DISH (1:43)

Money talks are getting spicy in the dating scene lately! As traditional gender roles shift and women gain financial independence, we’re seeing folks vet potential partners on money manners as much as romance. These matches are being referred to as “financial flames”.

In this week’s episode, we’re exploring whether getting fiscal can actually bring couples closer. Can shared finance goals and tools lead to greater understanding? Does splitting the check change the power balance? There’s a new “norm” in town!

LANE MOORE (9:39)

This week, we welcome Lane Moore! She is an award-winning writer, actor, comedian, and host of the “I Thought it Was Just Me” podcast on Patreon. Her best-selling books are titled “How to Be Alone: If You Want To, and Even If You Don’t,” and “You Will Find Your People: How to Make Meaningful Friendships as an Adult”. 

Lane also has a brand new book out: “You’re Not the Only One Effing Up: Breaking the Endless Cycle of Dating Mistakes.” Her comedy show Tinder Live has been praised by the New York Times, Spin Magazine, Entertainment Tonight, CBS, Timeout New York and New York Magazine. 

(10:40) What is Tinder Live?

Online dating can unearth some wild profiles. In her show Tinder Live, Lane lets audiences in on the swiping experience by projecting her actual app on stage. The crowd votes left or right, intentionally opting for oddball picks – we’re talking near-naked selfies, an excess of fish pics, even a guy snuggling roadkill!

While played for laughs, Lane takes a thoughtful approach, too. She critiques profiles constructively and finds that even chaotic matches can spark insightful conversations around better self-expression. “So it’s really taking that and turning it into something cathartic and really funny. There is an element of Tinder life that is also educational,” Lanes says.

(13:37) When is a Red Flag not a Red Flag?

Tired of toxic dating advice based on oversimplified “red flags”? Lane urges more nuance when evaluating relationships. She pushes back on rigid rules that write people off—like the trope that a guy not close to his mom spells trouble. Her own difficult upbringing taught Lane that family estrangement doesn’t define someone’s worth.

Lane unpacks the problematic “life hack” mentality around modern dating in favor of more compassionate understanding between partners.

(19:18) What About the Cat Dudes?

The data shows dudes with cats in dating profile pics get fewer messages. But Lane argues our reaction says more about lingering gender norms than the guys. “To me, it’s so obvious what that is. It’s because we think of cats as being a more feminine animal, like having a more feminine energy than a dog.” Lanes shares.

Lane calls BS – caring for pets shows compassion and consistency, right? And cats selectively give their love – so “cat guys” put in the effort!

(21:34) Green Flags

Forget red flags – Lane says start spotting relationship green flags! Instead of worrying what your date thinks, take note of how they make you feel. Do they bring fun energy that helps you relax and be yourself? Or are you working overtime to fill awkward silences and prop up bad convos?

Pay attention to that instinct telling you, “this kind of sucks.” You shouldn’t have to perform extreme emotional labor to save lackluster dates! As Lane puts it, dating is “an interview” to see if you both impress each other with natural chemistry and authenticity.

Be sure to check out the Tinder Live tour. Dates are listed at LaneMoore.org.  Her new ebook and audiobook You’re Not the Only One F*cking Up: Breaking the Endless Cycle of Dating Mistakes is out now and available exclusively from Everand.

DEAR DAMONA (29:14)

Submit your questions on Instagram, X, TikTok or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

Anonymous DM from Instagram:

• Could you add some nuance to the popular boring equals healthy advice? I understand it from an attachment perspective. But let’s assume I’ve done the inner work. I have found that boring just sometimes equals boring.  I fully agree with your four pillars and wonder where things like intellectual connection and humor/laughter fit in because they aren’t often addressed in dating advice. I am rarely attracted to someone for their physical appearance. The “spark” for me is a good conversation that occasionally goes deep and laughs. So if that’s not there after one or two phone calls and or dates, I usually END things. Am I being short-sighted? I always try to give the benefit of the doubt, but it’s such a fine line between giving a connection time to bloom and leading someone on – of which I’ve been accused. Thanks.

As we approach Valentine’s Day, let’s shift our focus from the idyllic scenes painted by Hallmark, See’s, and Tiffany’s. Instead, let’s embrace the essence of the holiday: LOVE. 

Our esteemed guest, MJ Harris, author of “Get The F*ck Out Your Own Way,” joins us to reveal the secrets of empowering your relationships—be they personal, platonic, or romantic. He challenges conventional notions, including the surprising perspective that there might be nothing wrong with ghosting?! As a seasoned world traveler, MJ will also share The Tinder Rule for those navigating the dating scene abroad. Get ready for insightful revelations and a dose of love wisdom!

But first, we have the Dating Dish this week, and it’s right on time for Valentine’s Day!

DATING DISH (2:34)

Damona explores the phenomenon of “avalanching” highlighted by Stylist Magazine – a frantic, quantity-centric dating approach fueled by the pressure of Valentine’s Day. Damona’s upbeat advice centers around intentional dating. She advises singles to avoid the rush and focus on slow love.

Citing Sylvia Liza Loni, an expert from  FindingtheOne.com app, Damona shares three quick tips on capturing the conclusion of peak dating season and maybe even a date for Valentine’s Day!

MJ HARRIS (13:36)

MJ Harris is an international speaker, social media celebrity, and the author of the new book, “Get The F*ck Out Your Own Way: A Guide to Letting Go of the Sh*t That’s Holding You Back”. MJ has been featured by Oprah, USA, Today and Black Enterprise. He’s also the CEO and founder of the MJ Harris Financial Group.

(16:20) Are You a Recovering People Pleaser?

People pleasing is a hard habit to break, but being aware of this tendency allows you to pause and respond intentionally. As MJ says, anytime someone presses you to answer right away, that likely serves them more than you. A thoughtful pause is so much better than quick reactions we might regret. Moving too fast or on auto-pilot can mean ignoring our needs and wants.

MJ gives himself space when asked for something: “I am conscious of processing my feelings so my decisions reflect my best interest – not just pleasing others.”  

(23:10) No is a Complete Sentence

Saying “no” challenges even the most caring people pleasers. We tend to over-explain, trying to talk ourselves into a “yes” instead of setting clear boundaries. 

MJ suggests that “no” can be a complete sentence and it doesn’t have to be blurted out directly. Give yourself permission to phrase it in whatever format feels most comfortable to you. The priority becomes honoring what you actually want or don’t want to do. 

(27:50) Ghosting is ok??

MJ doesn’t demonize ghosting. He says that ending communication abruptly causes real hurt, but not everyone has the tools to confront disappointment directly due to past trauma. Rather than excuse it, he suggests accepting that ghosting exists as an unfortunate dating reality. 

He says that staying attuned to subtle cues along the way can alert you to a potential situation. MJ shares his own ghosting experiences saying, “there were normally some nonverbal cues along the way that I may have kind of overlooked,” he says. Essentially, if texts decline in warmth and plans grow platonic way before the final silence forms, a fade is brewing. 

(37:17) The Tinder Rule

MJ shares his “Tinder rule”. Different cultures find different looks attractive. So vet destinations beforehand by asking locals if your vibe resonates there.

When asked about LDRs, MJ says, “I think that long-distance relationships can work if there is the prospect of you two living in the same place within a very clear timeline.” Most important emotional needs don’t get met without frequent in-person contact, but for busy careers, scheduled mini-reunions help maintain bonds.

Follow MJ on Instagram @MJHarrisSpeaks and grab a copy of his book, Get The F*ck Out Your Own Way, wherever books are sold!

DEAR DAMONA (41:23).

Submit your questions on Instagram, X, TikTok or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

Instagram DM from Pearl:

• I’m going back on the apps after having been on and off for a few years now. What do you do when you see men you’ve previously matched with, went on one or multiple dates with, or have slept with?