Honest dating advice for single men from two women. Dating expert Gracie Pleschourt (@datingwithgracie on IG) and certified life coach Tracy Pleschourt break down real dating questions, real struggles, and what actually works in modern dating.
Each week, they dive into listener-submitted questions about their toughest dating challenges and deliver unfiltered, constructive feedback. Submit yours here: https://forms.gle/34JLMADMcxhqdb7X7
Want help finding the podcast that best serves you? Check out our podcast guide: https://claude.ai/artifact/LjExhjNNe6YRmHDUbKoQs1
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What Women REALLY Want! A Single Woman Tells Men the Truth (Ep. 100)
Wednesday, October 28, 2026 • Duration 01:11:17
🎉 EPISODE 100: What Women REALLY Want! Straight From a Single Woman Herself!
For 100 episodes, Gracie and Tracy have been answering men's biggest dating questions. But this week, we're doing something different. We're putting a REAL single woman in the hot seat!
Meet Jennifer. She's 56, divorced, raising three teenage boys, successful, independent, and ready to find love. So why has she only been on ONE date in the last TWO YEARS?
In this milestone episode of the Just Ask Her Podcast, we're getting brutally honest about modern dating, why men hesitate to approach women, what makes a great first date, and what women actually want from men.
Jennifer shares why she's done with dating apps, what turns her on and off during a date, why she wants a man to take the lead, and what dating a single mom really looks like.
We also tackle the great first-date debate: Who pays? Are flowers too much? Should you call instead of text? And is using a coupon at dinner an automatic deal breaker?
Plus, Jennifer plays Rizz or Cringe, where she gives her unfiltered opinions on common dating moves.
And here's the twist. Jennifer is actually open to dating one of our listeners!
Could we be turning Just Ask Her into a matchmaking podcast? Stranger things have happened!
If you're looking for dating advice for men, relationship advice, dating confidence, tips for meeting women in real life, or an honest female perspective on finding love after divorce, this episode is for you.
100 episodes. Countless dating questions. And one single woman who might just find her match.
🎧 Listen now and celebrate episode 100 with Gracie, Tracy, and Jennifer!
What women want in a man, Dating advice for men, How to approach women, What makes a man attractive, How to meet women in real life, Dating mistakes men make, First date tips for men, Dating over 50, Dating after divorce, Dating a single mom, How to get a second date, Who pays for the first date, Why women hate dating apps, How to build dating confidence, Signs a woman wants you to approach
Is She Losing Interest or Are You Overthinking It? (Ep. 99)
Wednesday, October 21, 2026 • Duration 36:20
When should you pursue a woman, when should you back off, and when is it time to take the hint? Dating would be a whole lot easier if everyone came with an instruction manual. Unfortunately, they don't, so Gracie and Tracy are here to help!
In Episode 99 of the Just Ask Her Podcast, dating coach Gracie and her mom, Certified Life Coach Tracy, tackle three dating dilemmas involving matching energy, texting anxiety, long-distance relationships, mixed signals, emotional availability, rejection, and dating confidence.
First, a divorced man wonders whether matching a woman's energy is a sign of healthy self-respect or just another way of protecting himself from rejection. Is there a difference between confidently pursuing a woman and desperately chasing her?
Next, a man navigating a long-distance relationship is getting some serious emotional whiplash. Their chemistry is incredible in person, but her inconsistent communication and reluctance to commit have him questioning everything. Is she genuinely taking things slow, emotionally unavailable, or keeping him around as a placeholder?
Finally, we have possibly the most creative dating attempt in Just Ask Her history! A man interested in a romance novelist sends her a full dating resume, complete with ex-girlfriend testimonials and a personalized Cameo from her favorite Survivor contestant. There's just one tiny problem. She never responded! Now he's about to see her at a book event. Should he bring it up, pretend it never happened, or accept that silence might already be his answer?
Throughout the episode, Gracie and Tracy break down the psychology of dating, healthy communication, relationship expectations, overcoming rejection, and building the self-confidence to pursue women without losing yourself in the process.
Whether you're struggling with dating apps, wondering if she's interested, navigating an undefined relationship, or learning how to stop chasing women, this episode is packed with practical dating advice for men who want healthier relationships and genuine romantic connections.
FOUR YEARS Together... And She STILL Won't Commit?! (Ep. 98)
Wednesday, October 14, 2026 • Duration 46:33
Are women secretly keeping a roster of men? Is taking a break in a relationship just a nicer way of breaking up? And how long is TOO LONG to wait for someone to finally choose you?
This week on the Just Ask Her Podcast, hosts Gracie and Tracy are tackling three dating dilemmas that expose some uncomfortable truths about modern dating, relationship boundaries, emotional availability, and knowing when it's time to walk away.
And trust us, some of these guys REALLY need to hear this.
One man discovers that the woman he thought he had an amazing first date with may have been entertaining several other men at the same time. Now he's questioning her honesty, integrity, and whether dating multiple people is a massive red flag.
After experiencing betrayal in his marriage, another listener finds himself in a painfully familiar situation when his new girlfriend asks to put their relationship on pause. Should he wait for her to figure things out, or is walking away the healthiest decision?
Our final listener has spent four years investing in a woman he barely sees. We're talking unanswered messages, canceled plans, little physical time together, and an entire YEAR waiting for a response to a heartfelt letter. At what point does patience stop being a virtue and start becoming self-sabotage?
In this episode, we're talking about:
Dating multiple women or men before exclusivity
Dating rosters, honesty, and relationship red flags
How to recognize mixed signals and emotional unavailability
Relationship breaks versus breakups
Setting healthy boundaries after betrayal or divorce
Do Women Really Speak in Code? | Truth or Trash (Ep.2)
Sunday, October 11, 2026 • Duration 18:57
Welcome back to Truth or Trash, the Just Ask Her series where Gracie and Tracy venture into one of the scariest places on the internet: Gracie's social media comment section.
This time, they're putting more dating advice, assumptions, hot takes, and questionable internet wisdom to the test.
Do women really "speak in code"?
Are women secretly testing men?
Can someone else actually hurt your feelings?
Do actions speak louder than words?
Should men always be expected to approach women, or should women start making the first move too?
Gracie and Tracy break down five real comments and decide whether each one is TRUTH or TRASH.
Along the way, they get into why some women struggle to communicate what they actually mean, how men can respond to mixed signals without playing guessing games, why mature relationships require direct communication, and how fear of rejection is affecting BOTH sides of modern dating.
Because while some women are afraid approaching a man will make them look desperate, some men are afraid approaching a woman will make them look creepy.
And then everyone wonders why nobody is meeting anybody.
If you're navigating modern dating, dating apps, approaching women, fear of rejection, mixed signals, communication in relationships, women's dating signals, men's dating advice, dating confidence, relationship advice, dating myths, how to talk to women, how to know if a woman is interested, or who should make the first move, Gracie and Tracy have some thoughts.
We’ve Been Dating 5 Months... I Don’t Know Her Last Name (Ep.97)
Wednesday, October 7, 2026 • Duration 36:49
Dating can get complicated fast when fear of rejection, overthinking, mixed signals, and relationship uncertainty start running the show. This week on Just Ask Her, Gracie and Tracy are tackling two dating dilemmas that ultimately come down to one question: Are you willing to risk an uncomfortable answer to finally get some clarity?
First, a listener writes in after two divorces and years of relationships that left him questioning his confidence and self-worth. Now that he's done the work to heal and figure out what he actually wants in a partner, there's a new problem: he freezes around women he's genuinely attracted to.
Then things get... weird.
Another listener has been dating a woman for FIVE MONTHS. They spend hours together. They go to dinner. They exchange gifts. He's bought her roses. Sounds promising, right? Well... he doesn't know her last name. He doesn't know exactly where she lives. They haven't kissed, held hands, or even really hugged. Oh, and he's afraid asking about any of this might push her away.
Gracie and Tracy have questions. A lot of questions.
This episode gets into dating confidence, rejection, approaching women, overthinking in dating, scarcity mindset, relationship anxiety, mixed signals, dating boundaries, emotional availability, communication, trust, self-esteem, relationship uncertainty, modern dating, men's dating advice, how to talk to women, how to build confidence with women, and how to know when it's time to define a relationship.
Because sometimes the solution isn't another dating strategy.
Sometimes you really do need to Just Ask Her.
🎙️ Hosted by
Stop Waiting for Her to Choose You | Dating Advice for Men (Ep.96)
Wednesday, September 30, 2026 • Duration 51:25
Are you actually making choices in your dating life, or are you waiting for someone else to make them for you?
This week on Just Ask Her, Gracie and Tracy tackle three very different dating dilemmas that all have one thing in common: letting someone else take the driver's seat in your dating life.
First, a 25-year-old man is recovering from the end of a nearly five-year relationship and trying to figure out whether he actually wants his ex back or just wants the heartbreak to stop. After years of changing himself, chasing connection, and trying to be "enough" for his partner, how does he rebuild his confidence without turning healing into another performance?
Then, Jacob is dating a woman who had just gotten out of a relationship days before their first date. The chemistry started strong, but now the texting has slowed down and the energy feels different. Is she emotionally unavailable? Is he becoming the rebound? Should he give her space, walk away, or let her set the pace?
Finally, our returning submitter Travis is back after putting himself out there at singles events in Dallas. Some have gone well. Others have felt like walking into a company Christmas party where everyone knows each other except you. So what do you do when a singles event feels cliquey, awkward, or completely closed off?
From breakup recovery and emotional availability to singles events, dating confidence, communication, self-respect, anxious attachment, meeting women, overcoming rejection, and taking control of your dating life, this episode is all about one big shift:
Stop waiting to be chosen.
Plus, Gracie and Tracy somehow end up debating what Just Ask Her listeners should be called, discover they still haven't figured it out after 96 episodes, and immediately demonstrate exactly why it has taken them 96 episodes to figure it out.
Stop Trying to Decode Her Mixed Signals (Ep.95)
Wednesday, September 23, 2026 • Duration 40:10
Mixed signals are confusing. But at what point do you stop trying to figure out what SHE means and start deciding what YOU actually want?
This week on the Just Ask Her Podcast, Gracie and Tracy tackle three dating dilemmas involving mixed signals, fear of rejection, vulnerability, friendship, breakups, and the exhausting habit of trying to decode someone else’s behavior.
First, a guy has been told very clearly that she DOESN’T want to date him... except she keeps kissing him. Repeatedly. So what exactly are you supposed to believe when her words say “no” but her actions keep handing you a “maybe”?
Next, a listener realizes he has a habit of rejecting himself before a woman ever gets the chance. When a promising long-distance connection suddenly goes quiet, he assumes the worst and emotionally checks out. Plot twist: she comes back asking where HE stands.
Finally, after the end of a seven-year relationship, one listener develops feelings for the female friend who helped him through the breakup. Is she interested? Is he rebounding? Is he even ready for another relationship? And should he be trying to decode her mixed signals when he already admits he isn't ready to date?
Plus, Tracy explains what being a certified life coach actually means, Gracie talks about how life coaching tools helped transform her own dating experience, and somehow the phrase “have your cake and eat it too” sends the entire episode into an important investigation of cake, chocolate, peanut butter, Dairy Queen ice cream cakes, and why anyone would acquire cake without intending to eat it.
If you struggle with dating anxiety, mixed signals from women, fear of rejection, overthinking dating, dating confidence, setting boundaries, emotional regulation, vulnerability, self-rejection, relationship anxiety, getting over an ex, understanding women, or knowing when to move on, this episode is for you.
The Fear of Rejection Is Keeping You Single (Ep.94)
Wednesday, September 16, 2026 • Duration 56:09
What if the thing you’re doing to protect yourself from rejection is actually keeping you alone?
This week on Just Ask Her, Gracie and Tracy tackle three very different dating dilemmas that all have one thing in common: fear. Fear of rejection, fear of getting hurt again, and fear of finally asking the question that could give you the clarity you need.
First, a 58-year-old man struggling to move on after betrayal and infidelity ended a relationship he still can’t stop thinking about. How do you rebuild trust, stop comparing new women to an ex, and open yourself up to love again after heartbreak?
Next, a divorced man travels from San Diego to Zurich to visit a longtime female friend after their connection begins feeling like something more. But when he finally brings up a long-distance relationship, everything changes. Did he misread the signs, or is this exactly why honest communication and choosing clarity over guessing matter so much in dating?
Finally, a 56-year-old man who has never been on a date admits he intentionally pursues unavailable women because he’s terrified of rejection. Gracie and Tracy break down why avoiding rejection can become a self-fulfilling cycle, how your brain turns fear into evidence that you “can’t” date, and why learning to tolerate uncomfortable emotions can completely change your dating life.
Plus, Gracie and Tracy discuss the controversial Callaway Golf ad, their family trip to Seattle, and somehow end up debating whether “Rick Hopper” is secretly a Stranger Things character.
If you’re struggling with dating anxiety, fear of rejection, getting over an ex, infidelity, heartbreak, dating after divorce, approaching women, the friend zone, long-distance relationships, building confidence with women, emotional availability, relationship anxiety, or finding a healthy relationship, this episode is for you.
Just Ask Her helps single men date with confidence, understand women, build genuine connections, and create healthier relationships without playing games or pretending to be someone they’re not.
TRUTH or TRASH? We React to Men’s Dating Hot Takes (Ep.1)
Tuesday, September 15, 2026 • Duration 22:17
TRUTH or TRASH? 🗑️ Gracie and Tracy are diving into the comment section, and nobody is safe.
In this new Just Ask Her segment, Gracie and Tracy react to dating advice, hot takes, and questionable wisdom pulled straight from Gracie’s social media comments. Should men take dating advice from women? Should women make the first move? Is it okay to approach women at the gym, bar, or out in public? Do “high quality women” get the ick? And apparently, should every single man just get a dog?
Some takes are truth. Some are trash. And some earn a spicy rant.
If you’re a single man navigating modern dating, approaching women, making the first move, building confidence, or trying to separate good dating advice from absolute garbage, welcome to Truth or Trash.
Does She Like You? You’re Asking the Wrong Question. (Ep.93)
Wednesday, September 9, 2026 • Duration 47:13
What if uncertainty isn’t the problem with dating? What if learning how to handle it is the skill that changes everything?
In this episode of Just Ask Her, Gracie and Tracy tackle three dating dilemmas from men at very different stages of life, all struggling with the same thing: trying to know the outcome before taking the next step.
First, a great first date turns into mixed signals, canceled plans, Instagram comments, and silence. Is she genuinely interested or stringing him along?
Next, a 49-year-old listener struggling with social anxiety asks how to become more attractive to women. But his real challenge might not be attraction at all.
Finally, a 23-year-old wants to turn a college friendship into something more without making things awkward. Should he tell her he’s interested? How much should they text first?
Plus, Gracie shares an incredible dating story involving a bachelorette party, country dancing, a Pitbull costume, a bald cap, a wrong phone number, and some impressive LinkedIn detective work.
Whether you’re dealing with mixed signals, dating anxiety, rejection, overthinking, texting, approaching women, asking someone out, building confidence, or figuring out if she likes you, this episode is about getting comfortable with not knowing what happens next.
Because dating confidence isn’t knowing she’ll say yes. It’s knowing you’ll be okay with the answer either way.
Have a dating dilemma? Submit yours for a chance to be featured on a future episode.
👍 Like, subscribe, and share Just Ask Her with someone who could use a little dating clarity. Follow Gracie at Dating with Gracie on Instagram, TikTok, YouTube, and Facebook.
Dating advice for men, How to know if she's interested, Mixed signals from women, Stop chasing women, Matching energy in dating, Relationship advice for men, Dating confidence for men
Avoidant attachment and one-sided relationships
How to stop chasing someone who isn't reciprocating
Dating with confidence, self-respect, and intention
Knowing when to walk away from a relationship
Whether you're struggling with modern dating, recovering from heartbreak, navigating an uncertain relationship, or wondering why someone won't make you a priority, Gracie and Tracy are here to help you stop overthinking, recognize your worth, and take back control of your dating life.
Have you ever dated someone who was seeing multiple people? Have you taken a relationship break that actually worked? Or have you stayed in a one-sided relationship longer than you should have?
Tell us in the comments! We want to hear your experiences.
Dating advice for men, relationship advice for men, modern dating, dating red flags, dating multiple people, relationship boundaries, dating confidence, Just Ask Her Podcast
Some of them are truth.
Some of them belong directly in the trash.
🗑️ Welcome to Truth or Trash.
Let us know in the comments which takes YOU think are truth and which ones are complete trash.
dating advice for men, men's dating advice, fear of rejection in dating, how to approach women, dating confidence, how to talk to women, dating anxiety, relationship uncertainty, mixed signals in dating, modern dating advice
Got a name for the Just Ask Her community? PLEASE help them. Drop it in the comments. Maybe we can solve this before Episode 100.
🎙️ Just Ask Her is hosted by Gracie and Tracy, helping single men date with confidence, understand women, build stronger relationships, improve communication, overcome dating anxiety, and create the dating life they actually want.
dating advice for men, relationship advice for men, dating podcast for men, how to meet women, how to talk to women, dating confidence, modern dating advice, dating coach for men, how to get over a breakup, breakup recovery for men, moving on from an ex
Just Ask Her helps single men stop guessing, date with confidence, understand themselves better, build healthier relationships, and connect with real women without turning every text, kiss, silence, or vague “maybe” into a full-scale criminal investigation.
And since apparently this is important now: What’s your favorite kind of cake? Drop it in the comments. 🎂
mixed signals from women, dating advice for men, how to know if she likes you, understanding women, fear of rejection, dating confidence, dating anxiety, self-rejection in dating, relationship advice for men, dating podcast for men
Have a dating dilemma of your own? Submit it using the link in the show notes, and Gracie and Tracy may answer it on a future episode.
dating advice for men, fear of rejection, dating confidence, relationship advice for men, how to approach women, how to talk to women, how to get over an ex, dating after divorce, emotionally unavailable women, fear of dating
