Love After 50: From First Date to Engagement

How do you become more emotionally available in dating? In this episode, we discuss some simple steps you can take today. — Listen to the story of Kat and Shawn, a couple who met in their mid-50s. I worked with Kat before, during, and after she met Shawn, and they are a living example of […]

love after 50

How do you become more emotionally available in dating? In this episode, we discuss some simple steps you can take today.

Listen to the story of Kat and Shawn, a couple who met in their mid-50s. I worked with Kat before, during, and after she met Shawn, and they are a living example of how to find love after 50 and make the relationship work. They are engaged, living together, and navigating every up and down that comes with relationships later in life.

In this episode:

  • What makes a relationship after 50 work well
  • How to design healthy partnership
  • Obstacles that come up in relationships and how to work through them
  • How to know if they’re the right one for you

EP 697: Kat and Shawn – Falling in Love After 50, The Journey From First Date to Engagement

From Kat and Shawn

“We met online in our mid-50s, and the chemistry and compatibility were amazing from the start. We both value good communication and personal and relational growth. When we find ourselves at a crossroads, it’s extremely helpful to work with Sandy. She’s able to hear and understand BOTH our perspectives and helps us consider alternative ways of seeing our challenges. She gives us the tools to continue to build a healthier relationship.

We return to these new insights frequently and appreciate how much better our relationship is with the addition of an expert. She recently helped us overcome a big issue that was keeping us stuck. Later that day, on August 5th we got engaged! We’re grateful for a relationship that feels secure, loving, and supportive.”

Kat and Shawn

Highlights from the podcast

Tell us a little about your past relationships before you two met.

Kat: Divorced twice, running a business, raising two kids. Took a long time off of dating until kids were in college. Used to date guys who shared common interests. Hired me to be more intentional

Shawn: Divorced seven years, dated on and off. Stopped dating a bit before meeting Katherine. Didn’t have a high level of self-awareness or a partner with similar values before meeting Kat.

How did you meet?

Kat: I reached out to Shawn on Match and met for coffee. We were together for ten minutes, then met for a walk the next day. There was chemistry right away, and I had to intentionally slow things down. 

Shawn: We had communicated for about a week before meeting, and there was instant chemistry when we met. I loved her humor. So I asked her out again for the next day.

How have you designed your partnership?

We have calendars and schedules. We are our favorite people to be with, but we also make sure to have time outside of the house on our own. We have a travel calendar for travel together and apart. We try to balance all of that. We talk about finances and long range goals.

What are some of the obstacles you’ve faced, and how have you overcome them?

Kat: Slowing down has helped us create a strong foundation to overcome obstacles.

The first disharmony was when I was in Africa for three weeks. It brought up insecure feelings in Shawn. Our insecurities are at the heart of every roadblock.

Shawn: Saying you have insecurity is much different from feeling it. We prioritize honesty above all things. And we agree that omissions are dishonesty. We own our insecurities. We first look at ourselves and ask if it’s something from our past or our triggers.

How has your relationship evolved over the past two years?

Kat: We repair quickly. We try to talk things out as soon as possible. We pray together daily. One of us is always showing up for the other. We have a white couch that we call our therapy couch where we talk everything out. We even created a breakup plan so we have guardrails on our relationship and will seek out three therapy sessions before making a decision to break up. 

Blending our finances was challenging. I come from fear/scarcity and Shawn comes from an abundance mindset. I had to challenge childhood beliefs and communicate my fears to Shawn. We both have our teams for support which sometimes is more helpful than speaking to each other.

Shawn: I speak to other men who are committed to their partners, men who will call me out on my BS and be very honest with me.

What are your final words of advice for anyone who wants to go on their last first date?

Kat: What worked great for us was to take things really slow physically. I had a schedule about what was and wasn’t allowed, so the chemistry wouldn’t cloud my judgment. 

Shawn: Early on, rigorous and deliberate honesty. Share things that you’re not proud of about yourself. Find a reason to be as honest as possible. It’s one of the most important things you can do. I learned so much about her when I was brave and shared with her.

Watch this episode on YouTube


Please subscribe/rate and review the podcast here.

Apply to get FREE coaching on the podcast: https://bit.ly/LFDradiocoaching 

FREE download: “The Green Light Guide to Dating After 50: How to Show Interest Without Chasing” https://lastfirstdate.com/green-light-guide/

If you’re feeling stuck in dating and relationships and would like to finally find love, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

The Questions Women Over 40 Need to Ask Before Getting Invested in a Man

Before getting invested in a man, what are the questions women over 40 need to ask? Tune in to this episode to find out! — Before getting invested in a man, what questions should women over 40 ask their partners? Marcelle LeBlanc is an entrepreneur, speaker, and founder of The Conversation Architect. After rebuilding her […]

before getting invested in a man

Before getting invested in a man, what are the questions women over 40 need to ask? Tune in to this episode to find out!

Before getting invested in a man, what questions should women over 40 ask their partners? Marcelle LeBlanc is an entrepreneur, speaker, and founder of The Conversation Architect. After rebuilding her life following divorce, she discovered that one honest conversation can change the course of a life. Today, she teaches women the skill of having difficult conversations so they can gain clarity, trust themselves, and create lives that align with who they truly are.

In this episode:

  • Why “going with the flow” can cost women clarity
  • What needs to be said before deeper commitment
  • How honest conversations create healthier dating choice

EP 721: Marcelle LeBlanc – The Questions Women Over 40 Need to Ask Before Getting Invested in a Man

Highlights of this episode:

Conversation architect & purpose

  • Marcelle LeBlanc explains her role as a “conversation architect”: teaching people (especially professional women) to have one clear conversation that prevents years of silent resentment or wasted time.
  • Core belief: many relationship breakdowns stem from conversations not happening, not from lack of feeling or intelligence.
  • Goal: help clients identify values and non-negotiables quickly and use brief, skillful conversations (not months of therapy) to get clarity or change trajectory.

Framework & skills for difficult conversations

  • Start by clarifying the heart of the issue: separate facts from opinions, and be specific about behavior (not labels like “unreliable”).
  • Define the desired behavior and what success looks like, plus the real impact of the behavior on you.
  • Keep the conversation focused on one issue at a time; avoid “and you did this” piling-on.
  • Use a concise template: state the agreement/behavior, describe the impact on you, state the desired outcome, then ask for agreement (e.g., “Can you agree to that?”).
  • Prepare notes and rehearse to avoid rambling; allow silence and resist editing/self-sabotage mid-conversation.
  • If the person is unreceptive or defensive, offer to reschedule for a better time rather than escalate immediately.
  • Treat dating like a job interview: observe actions as data about alignment with your values and time.

Practical examples & outcomes

  • Lauren story: choosing one non-negotiable, having a prepared conversation, partner responded “I felt it too” — conversation restarted the relationship rather than ended it.
  • Household chores example: specific script given to address missed chores (name the agreement, explain emotional impact, request equitable action, ask for agreement).
  • Workplace example: manager labeled an employee “unreliable;” a fact-based conversation revealed lack of gas money, leading to an immediate, simple fix.
  • Small, frequent honesty prevents emotional accumulation and catastrophic blowups later.
  • Clarity exercises: value-lists and specificity (example of a man who carried a 100-item list; distillable to core values) help recognize fit quickly.

Watch this episode on YouTube here:

Connect With Marcelle


Please subscribe/rate and review the podcast here.

Send me your dating dilemmas to be featured in an upcoming episode: https://tinyurl.com/datingdilemma

If you’re feeling stuck in dating and relationships and would like to finally find love, apply for a complimentary 30-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

Seven Words That Can Change Your Life

Jerry Giordano wrote a book about seven words that can change your life. Find out what they are in this episode of Last First Date Radio! — Did you know that seven words can change your life? Jerry Giordano is an award-winning advertising copywriter/Creative Director working and living in NYC, Chicago, Los Angeles, Austin and […]

change your life

Jerry Giordano wrote a book about seven words that can change your life. Find out what they are in this episode of Last First Date Radio!

Did you know that seven words can change your life? Jerry Giordano is an award-winning advertising copywriter/Creative Director working and living in NYC, Chicago, Los Angeles, Austin and Dallas. He is a co-producer of TEDx events, penned four screenplays, studied comedy at Chicago’s Second City, and performed sketch comedy in NYC and LA. He collects old cameras, photographs manhole covers, is a JFK assassination nut, meditates, and lives in the moment. He’s also the author of Your 7 Words to a Happier You; unlock the story sabotaging your relationships

In this episode:

  • What is “Your 7 Words to a Happier You” about?
  • What does “unlock the story sabotaging your relationships” mean?
  • What the discovery of the 7-word sabotaging story done for relationships 
  • What the 7 words have to do with getting into one dysfunctional or narcissistic relationship after another

EP 660: Jerry Giordano – Seven Words That Can Change Your Life

What is your new book, “Your 7 Words to a Happier You” about? 

I didn’t set out to write a book. I had been a hopeful romantic my whole life. In 2017, I was engaged to a woman who I thought was the love of my life. I had two failed marriages before I met her. My mom passed away and twelve days later, I got a breakup email from my fiancè. I was devastated and depressed. It was the lowest point of my life. I couldn’t stop crying – all the pent up feelings were coming out.

I started meditating successfully. That began to transform me. There were three meditations that helped me connect the dots of my life. The seven words came through and helped me through. It helped me turn my life around.

The three meditations were dots that needed to be connected.

One was three year old Jerry crying saying he couldn’t carry this anymore. Adult Jerry walks by and helps him.

I realized three year old me was upset, so I researched inner child and what happens at three. It’s the magic age. They start understanding cause and effect. They live in magic-think, dressing up as characters. Three year-old me was carrying something. What was it? What was he feeling? My mom had a baby when I was three, and I got less attention. I began to feel what he was feeling.

The seven words are a circle: 

The third word is the persona that we carry into the world, the mask. Mine was likable. That’s how I got attention. The sixth word is the sabotage word. I became subordinate to be likable. The seventh word is cycle. I repeated the pattern over and over. 

Please explain the subtitle of the book, “unlock the story sabotaging your relationships”.

The mask we show the world is sabotaging us. For me, it was “subordinate” so I didn’t rock the boat. Some sabotage words are run, rescue, hide, accommodate, shut down, become stoic. 

What has the discovery of your 7-word sabotaging story done for your relationships? 

Once I figured out the patterns of self-sabotage and made the unconscious conscious, I began to heal. I would catch myself falling back into those patterns and pull myself out of it. I was on a date, and I thought it was going well. She finished her drink and walked away without saying a word. The old Jerry would have blamed myself. New Jerry followed her to the valet. She said, “Are you stalking me?” I told the valet what happened and told her she was one of the rudest people I’d ever met. That was huge for me. That turned things around for me. I’m now in a seven year relationship with an incredible woman!

You talk about people getting into one dysfunctional or narcissistic relationship after another. What do your 7 words have to do with that?

Rescue, subordinate, likeable are words that attract narcissists. When you recognize those words and who you are, you can break the pattern and attraction to narcissists.

What are your final words of advice for anyone who wants to go on their last first date?

Figure out who you are first. Then, you put the unconscious story to rest and your dating life will change for the better.

Connect with Jerry

Watch this episode on YouTube


Please subscribe/rate and review the podcast here.

Apply to get FREE coaching on the podcast: https://bit.ly/LFDradiocoaching 

If you’re feeling stuck in dating and relationships and would like to finally find love, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

How to Break Free From Narcissistic Abuse

If you’ve ever experienced narcissistic abuse, this episode with Dr. Alina Kastner is for you. Learn how to break free! — How do you break free from narcissistic abuse? Dr. Alina Kastner, MSc, is a leading Vienna-based psychotherapist. Working with individuals, couples, and families across all backgrounds, she brings “bold systemic therapy with a twist” […]

narcissistic abuse

If you’ve ever experienced narcissistic abuse, this episode with Dr. Alina Kastner is for you. Learn how to break free!

How do you break free from narcissistic abuse? Dr. Alina Kastner, MSc, is a leading Vienna-based psychotherapist. Working with individuals, couples, and families across all backgrounds, she brings “bold systemic therapy with a twist” to match her clients’ fire and courage. Her specialty: promoting deeper intimacy, connection and clarity while helping people navigate trauma and narcissistic abuse; the latter of which was the focus of her doctoral thesis.

In this episode:

  • What exactly is narcissistic abuse, and why it’s so difficult for people to see when they’re experiencing it
  • The first step to protect yourself from a narcissist
  • The biggest misconceptions about narcissism in the media
  • How to tell the difference between an emotionally unavailable partner and a true narcissist
  • Small acts you can take to begin rewriting your story of narcissistic abuse

EP 706: Alina Kastner – How to Break Free From Narcissistic Abuse

Highlights of this Episode

What is narcissistic abuse – common signs
• Narcissistic abuse is primarily psychological: gaslighting, lack of empathy, exploitation for admiration (“supply”), envy, devaluation and discard.
• Victims feel confused, anxious, walk on eggshells, and may develop PTSD/C-PTSD.
• Pattern: intense love-bombing → gradual devaluation → isolation → increased confusion.

Who is vulnerable & why
• People raised with narcissistic or fragmented caregiving often unconsciously seek familiar (unhealthy) attachment patterns.
• Compassion toward family is different than compassion toward a romantic partner; trying to “fix” a narcissist rarely works.
• Highly compassionate people can be especially susceptible.

Healing and practical self-care steps
• Start small: meditation, breathwork, therapy, journaling. Break healing into manageable steps.
• Invite and feel painful emotions (e.g., use the “pain hour”) rather than only intellectualizing.
• Create must-haves / deal-breakers lists for relationships; be flexible on “nice-to-haves” but firm on non-negotiables.

Dating, differentiating avoidant vs narcissist, and co-parenting
• Avoidant vs narcissist: avoidants can usually self-reflect and are willing to work on attachment issues; narcissists lack empathy, deflect blame, and won’t respect boundaries.
• Early testing: look for consistency of actions with words over time; many red flags surface within weeks.
• Dating tips: prefer profiles/actions that “show” values (not just boastful claims); listen for listening, empathy, and groundedness.
• Co-parenting with a narcissist: aim for no emotional engagement; communicate facts neutrally; use lawyers if necessary; maintain modeled behavior for children.

Watch on YouTube

Connect With Alina


Please subscribe/rate and review the podcast here.

Apply to get FREE coaching on the podcast: https://bit.ly/LFDradiocoaching 

FREE download: “The Green Light Guide to Dating After 50: How to Show Interest Without Chasing” https://lastfirstdate.com/green-light-guide/

If you’re feeling stuck in dating and relationships and would like to finally find love, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

How to Heal Your Relationship

If you want to know heal your relationship, listen to this episode. Dr. Rachel Glik shares helpful tips to strengthen any relationship. — Rachel Glik is a licensed professional counselor with 30+ years as a couples and individual therapist in private practice. Since 2014, she has been a regular feature on the Fox 2 AM […]

heal your relationship

If you want to know heal your relationship, listen to this episode. Dr. Rachel Glik shares helpful tips to strengthen any relationship.

Rachel Glik is a licensed professional counselor with 30+ years as a couples and individual therapist in private practice. Since 2014, she has been a regular feature on the Fox 2 AM show in St. Louis as a relationship and mental health expert. Her book, A SOULFUL MARRIAGE: Healing Your Relationship With Responsibility, Growth, Priority, and Purpose was published February 4, 2025.

In this episode of Last First Date Radio:

  • The essential four pillars that can positively transform and heal your relationship
  • The eight friendships that can influence a relationship 
  • How to diffuse tension in an emotional argument using the love seat listening method 
  • Why we should reframe conflict as an opportunity for growth
  • One step someone could take today to create a stronger relationship

EP 646 : Dr. Rachel Glik – How to Heal Your Relationship

What are the essential four pillars that can positively transform and heal your relationship? 

  1. Pillar one: Responsibility. We’re each responsible for our happiness and well-being. We have to know ourselves and individuate.
  2. Pillar two: Growth. Most people struggle with the growth pillar. That’s where conflict comes in. We use our friction to grow individually and then together.
  3. Pillar three: Priority. We make each other the most important person in our lives besides ourselves. Nothing will come between our connection.
  4. Pillar four: Purpose. If we don’t have a sense that we make the world better through our bond, it’s a challenge. Extend out of your collective.

What are the essential eight friendships that can influence a relationship? 

  1. Emotional friendship. Your partner is a confidant. You trust them. They are attuned and you feel safe with them.
  2. Sexual and physical friendship. The physical is touching and holding hands. Sexual is how well you’re matched.
  3. Parenting friendship. Kids or pets – are you aligned?
  4. Financial friendship. Are there secrets? Lies? Is there a ‘we’?
  5. Recreational friendship. Do you have fun together, laugh, enjoy each other.
  6. Spiritual friendship. Share a similar mindset and view or support each other’s view.
  7. Domestic friendship. Do you do well as roommates? Does it feel democratic or harmonious?
  8. Community friendship. Part of an organization? Do you volunteer?

How do you diffuse tension in an emotional argument using the love seat listening method? 

It’s the opposite of the hot seat. When couples argue, we need to slow it down and take turns. One person is in the love seat. You listen and they talk. It’s structured and keeps the ego and reactive part of us at bay. Each person feels heard. Reflect back with active listening skills. Conflict is an opportunity to grow.

What is one step someone could take today to create a stronger relationship?

Show appreciation to someone who’s important to you. Pause, breathe, relax and open your heart to the experience of them in your life. 

What are your final words of advice for anyone who wants to go on their last first date?

Unless it’s really not good for you, allow yourself to embrace the imperfection of the relationship. Look out for where you’re searching for someone to complete you or be perfect. If there’s enough there and you feel you can grow together, normalize that every relationship has imperfections. 

Watch this episode on YouTube

Connect With Rachel


Please subscribe/rate and review the podcast here.

Apply to get FREE coaching on the podcast: https://bit.ly/LFDradiocoaching 

If you’re feeling stuck in dating and relationships and would like to finally find love, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

The Fears that Sabotage Relationships

What are the fears that sabotage relationships? Dr. Maria-Elena Lukeides helps us explore why good relationships fall apart. — What are the three key fears that sabotage relationships? That was the topic of discussion with Dr. Maria-Elena Lukeides. She is a Sydney-based Clinical Psychologist, meditation teacher, and pioneer in psychedelic-assisted therapy in Australia. With nearly […]

fears that sabotage relationships

What are the fears that sabotage relationships? Dr. Maria-Elena Lukeides helps us explore why good relationships fall apart.

What are the three key fears that sabotage relationships? That was the topic of discussion with Dr. Maria-Elena Lukeides. She is a Sydney-based Clinical Psychologist, meditation teacher, and pioneer in psychedelic-assisted therapy in Australia. With nearly 30 years in mental health, she integrates clinical psychology, neuroscience, mindfulness, and psychedelic therapy to explore trauma, healing, and human connection, drawing from both professional expertise and lived experience.

In this episode, we covered:

  • The three key fears that hold us back in life and love
  • What happens in relationships when people are unaware of the fears they carry
  • How to begin to overcome our fears and have better relationships with ourselves and others

EP 716: Dr. Maria-Elena Lukeides – The Fears That Sabotage Relationships

Highlights of this episode

Dr. Lukeides’ background & her core message

  • Central theme: The “Field of love” is a state of safety and fearlessness; fear = anything that pulls us out of that field.
  • Her key insight from personal experience: seeking external validation never fully heals inner wounds; self-love (unconditional acceptance of all parts of ourselves) is distinct from self-esteem (conditional, comparative).
  • Book coming out end of 2026: “No Parts Left Behind” with an emphasis on Internal Family Systems / parts work and reintegrating exiled parts.

Three core fear categories that sabotage relationships

  • Fear of weakness/vulnerability (survival/health): belief “I can’t cope” leads to avoidance of emotionally demanding growth.
  • Fear of incompetence/failure (skills/intellect): impostor syndrome, fear of criticism, avoidance of situations that risk perceived failure.
  • Fear of rejection/undesirability (social/attachment): early attachment wounds create expectations of exclusion and filter current interactions negatively.
  • All three originate from early experiences and form predictive “algorithms” that skew interpretation; healing requires re-examining our original conclusions.

Practical strategies for dating, boundaries, and relationship repair

  • Name and dialogue with our fears: anthropomorphize fears/parts. Ask what they are trying to protect you from.
  • Gentle, experimental exposure: “dance” of incremental self-disclosure (step forward, mirror, step back) rather than full neutralization of defenses.
  • Use self-compassion/parts work: bring exiled or shameful parts into a nonjudgmental “field of love.”
  • Go needs-first: articulate needs and boundaries early on in dating; sharing hurts and preferences is data, not aggression.
  • Test capacity early: small boundary checks (interrupting politely, asking for plans, noting treatment of waitstaff) reveal partner reliability.
  • Practical first-date tips: treat dating as play; use active/shared activities (museums, walks) to observe behavior; debrief post-date on curiosity, attraction, and reciprocity.
  • Stop compensating: avoid over-planning/paying/doing everything; lean back to see who can step up.

Watch on YouTube

Connect With Dr. Maria


Please subscribe/rate and review the podcast here.

Submit your dating dilemma to be answered on my podcast https://tinyurl.com/datingdilemma 

If you’re feeling stuck in dating and relationships and would like to finally find love, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

Communication Mistakes that Ruin Relationships (and how to catch them early)

Did you know that small communication mistakes are quietly ruining your relationship? Here’s how to prevent that from happening. — What are the communication mistakes that ruin relationships? Lior Illouz is the co-founder and CEO of Bonds, a PhD-backed AI relationship app with 10,000+ users, built with his childhood friend, clinical psychologist Dr. Lior Kritzman. […]

communication mistakes

Did you know that small communication mistakes are quietly ruining your relationship? Here’s how to prevent that from happening.

What are the communication mistakes that ruin relationships? Lior Illouz is the co-founder and CEO of Bonds, a PhD-backed AI relationship app with 10,000+ users, built with his childhood friend, clinical psychologist Dr. Lior Kritzman. A former Meta leader, husband who married at 38, and first-time father, Lior helps people catch the small communication patterns that quietly end relationships before they explode.

In this episode:

  • The small communication mistakes that can quietly end relationships
  • The gap between what we say and what we mean and why it grows over time
  • What predicts whether a relationship will last
  • How to spot your communication patterns early on in dating

EP 723: Lior Illouz – Communication Mistakes that Ruin Relationships (and how to catch them early)

Highlights of this episode:

Origins of Bonds app

  • Lior Illouz built Bonds from personal need after repeated short relationships and difficulty finding affordable, actionable help.
  • App goal: translate psychological principles into tailored, actionable daily habits and conversation practice to change behavior (not just provide generic advice).
  • Foundation: collaboration with psychologists and relationship experts; focus on measurable value (behavior change) over time spent in-app.

Common communication issues & practical fixes

  • Money disagreements
    • Root cause often fear or learned family narratives.
    • Effective approach: acknowledge fear, state needs, explain the “why,” and co-create solutions (e.g., softer goals vs. strict budgets depending on partner).
  • Not being heard / criticism vs. feedback
    • People often conflate judgment with feelings; reframe as specific requests/feedback and ask curiosity-driven questions.
    • Small, focused requests work better than overwhelming lists.
  • Emotional shut-down / defensiveness
    • Create safety: state positive intention, keep requests tiny, offer options to pause/resume conversation.
    • If the partner shuts down, gently name the observation in a nonaccusatory way (e.g., “It seems like this feels overwhelming; do you want to continue later?”).
  • Practical rehearsal
    • Role-play and simulated conversations help prepare and reduce robotic or unempathetic delivery.
    • Lior shared his own app practice: using simulated scripts improved a sensitive post-birth gift conversation.

AI, apps, and therapy: benefits & caveats

  • Benefits
    • AI/apps can give tailored reminders, conversational simulations, and habit-building nudges that scale therapy-like practices.
    • Real-world examples: users reported improved empathy with service workers and a partner moved to tears by a personalized handwritten-note gift idea prompted by the app.
  • Caveats
    • Generic LLMs can reinforce bias and lack nuance; output quality depends on input context and user honesty.
    • Trust and privacy matter: users need assurance their data won’t be sold or misused.
    • Best outcomes when apps are built with expert oversight (psychologists) and grounded in established frameworks (CBT, attachment theory, congruence/perceptual-gap work, love languages).

Watch this episode on YouTube here:

Connect With Lior and HeyBonds


Please subscribe/rate and review the podcast here.

Send me your dating dilemmas to be featured in an upcoming episode: https://tinyurl.com/datingdilemma

If you’re feeling stuck in dating and relationships and would like to finally find love, apply for a complimentary 30-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

5 Questions That Lead to Deeper Conversations in Early Dating

How do you have deeper conversations on a first date? These 5 questions will open up lively, informative, and connecting conversations. — Early dating doesn’t have to feel like an interview or a performance. The most meaningful connections grow when conversations move beyond small talk and into curiosity, values, and things you have in common. […]

deeper conversations

How do you have deeper conversations on a first date? These 5 questions will open up lively, informative, and connecting conversations.

Early dating doesn’t have to feel like an interview or a performance. The most meaningful connections grow when conversations move beyond small talk and into curiosity, values, and things you have in common.

If you’re dating and craving something real, these five questions can gently open the door to deeper conversations. They’re not about pushing intimacy too fast or interrogating your date to see if there are red or green flags. They’re about listening, noticing, and seeing whether there’s room to grow together.

1. What feels fulfilling to you right now?

This question reveals priorities. Some people light up talking about family, creativity, travel, volunteering, or even slowing down. Pay attention not just to the answer, but to the energy behind it. If you want to learn if their vision aligns with where you are in your life today, this is a great question.

2. What’s something you’re really enjoying or excited about these days?

This keeps the focus in the present and invites enthusiasm. It might be a hobby, a project, a class, a new routine, or even a simple pleasure. Notice what brings them joy, whether they’re stagnant or excited about life, and whether they’re open to sharing their interests with you. If you’re looking for someone who continues to engage in life no matter their age, this question is a good one.

3. Is there something you’re curious about or learning right now?

This question gently reveals mindset. Curiosity often signals openness and growth. It can lead to conversations about books, travel, creativity, or new experiences they want to explore. If you’re looking for a lifetime learner, this question is for you.

4. What do you value most in a close partnership?

Whether they mention trust, laughter, loyalty, growth, or they give you a blank stare, you’re learning what they consider essential in a relationship. If you want to learn if their values around partnership and relationships feel compatible with your own needs and desires, ask this question.

5. What helps you feel most connected to someone?

This question touches on emotional intimacy without being too heavy or intrusive. Some people feel connected through conversation, shared experiences, affection, or quality time. If you want to know how someone bonds, this can offer insight into whether your connection styles complement each other.

You certainly don’t need to ask all of these questions on one date. Let them unfold naturally. Depth isn’t created by the questions alone, but by listening and following up with curiosity.

The right conversations don’t rush the relationship or feel pushy. They help you get to know the most important qualities of the person you’re dating. And that’s where real connection begins.


FREE download: “The Green Light Guide to Dating After 50: How to Show Interest Without Chasing” https://lastfirstdate.com/green-light-guide/

If you’re feeling stuck in dating and relationships and would like to finally find love, sign up for a complimentary 45-minute love breakthrough session with me and explore how private coaching can help! https://lastfirstdate.com/application

Join my free Facebook group, Your Last First Date https://facebook.com/groups/yourlastfirstdate

Get my books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating: Empowering Women to Make Healthier Decisions in Love.

How to Be More Dateable

Julie Krafchick and Yue Xu believe everyone is dateable. If you’re struggling with modern dating, you must listen to this episode! — Want to know how to be more dateable? Julie Krafchick & Yue Xu are active daters turned dating insiders, and top influential voices of modern dating, relationships, and connection in the digital world. […]

dateable

Julie Krafchick and Yue Xu believe everyone is dateable. If you’re struggling with modern dating, you must listen to this episode!

Want to know how to be more dateable? Julie Krafchick & Yue Xu are active daters turned dating insiders, and top influential voices of modern dating, relationships, and connection in the digital world. They’re the authors of How To Be Dateable and the co-hosts of the hit podcast Dateable, which has been named one of the top podcasts about modern dating and relationships by the New York Times, The Huffington Post, Oprah Daily, and more. 

In this episode of Last First Date Radio:

  • What is “dating on your own terms”?
  • What the four dating archetypes represent: Achiever, Dreamer, Energizer, Maverick, and Thinker
  • Some of the traps that get in the way of finding your person
  • One of their favorite exercises from the book
  • Some of the key points they’re hoping readers will take away from the book

EP 645: Julie Krafchick and Yue Xu – How to Be More Dateable

How is your book different from other dating books out there?

We needed to let people know we don’t need to stay in the confines of modern dating. We hope it empowers people to date on their own terms. There’s so much negativity that doesn’t bring us to connection. There is a better way to date.

Tell us about the four dating archetypes that help you become more dateable.

Achiever: Go after what they want, achieve a lot. Downside is they’re not always present. They want to keep things going to get to the next stage. 

Dreamer: Wears their heart on their sleeve, they make great partners because they’re so warm. Where it doesn’t serve is getting lost in the fantasy by seeing the best in them and giving too many chances.

Energizer: Go, go, go daters. Back to back dates. Endless energy on dates. Downside is they don’t take time to pause and reflect on what works for them. All their energy is out, not in. They get drained.

Maverick: Very independent, high standards for self and others, hold your own in relationship, but runs at first sign of something hard to not get hurt. Needs to learn to run towards the person by getting curious and getting information instead of misinterpreting.

Thinker: They overthink, hesitate, are all in their head. They are people who think things through and are open to conversation. Downside is they go into analysis paralysis. They can lose track of the big picture.

What are some of the traps that get in the way of finding your person?

We believe everyone is dateable. What gets in our way is the traps of the modern dating culture. 

The Expectation of Love on Demand: We are in a fast culture. Uber, Amazon, Ubereats are all immediate. We often date like that, looking for an immediate spark.

Settling Paradox: This is where you don’t want to settle for the wrong person, but you settle for bad behavior. 

Validation Trap: Because of the mentality that you’re winning if you’re in a relationship and losing if you’re single put so much pressure on dating. We seek validation, but we’re not always aware of that. 

Relationship Chicken: We do everything in dating that’s the opposite of what we do in a relationship. Fox example, we play games with texting and waiting longer than the other. How can we treat dating as we would treat someone in a relationship. 

What are your final words of advice for anyone who wants to go on their last first date?

Don’t think about dates as first date. Anything can happen in life. Life doesn’t happen in a linear fashion. Bring your best self to every first date, and treat your relationship as a series of first dates. Be yourself, not a ‘date persona’. That’s when the right people come to fruition.

Connect With Yue and Julie

Watch this episode on Youtube


Please subscribe/rate and review the podcast here.

Apply to get FREE coaching on the podcast: https://bit.ly/LFDradiocoaching 

If you’re feeling stuck in dating and relationships and would like to finally find love, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life

The Art of Radical Listening

What is radical listening? And how can it help improve all our relationships? My podcast guest, Robert Biswas-Diener has the answers! — What is radical listening, and why is it important in our relationships? Dr. Robert Biswas-Diener is the co-author of the soon-to-be published book, Radical Listening, The Art of True Connection. He’s a researcher, […]

radical listening

What is radical listening? And how can it help improve all our relationships? My podcast guest, Robert Biswas-Diener has the answers!

What is radical listening, and why is it important in our relationships? Dr. Robert Biswas-Diener is the co-author of the soon-to-be published book, Radical Listening, The Art of True Connection. He’s a researcher, author, and consultant. His previous books include The Upside of Your Dark Side (New York Times Bestseller, 2014), and the 2007 PROSE Award winner, Happiness. He has presented keynotes to Lululemon, Deloitte, Humana, AARP, The World Bank, and others. In 2024, Thinkers50 named him one of the “50 Most Influential Executive Coaches in the World.” He lives in Portland, Oregon, where he enjoys drawing and rock climbing.

In this episode:

  • How Radical Listening moves beyond traditional active listening techniques
  • What people trying to accomplish when they listen
  • How the 6 Core skills of Radical Listening enable us to better communicate with
  • others
  • How Internal and External listening skills complement each other
  • How we can effectively overcome those barriers to better approach our conversations

EP 651: Dr. Robert Biswas-Diener – The Art of Radical Listening

How does Radical Listening move beyond traditional active listening techniques? 

Radical listening is not shocking, it’s about extending listening beyond what we do in active listening. One of the things we think is most important is that listening is about accomplishing things.

What are people trying to accomplish when they listen?

They’re trying to figure out your intention: do you want to be validated or solve problems? Both parties are equal in the relationship. When the speaker is speaking, they’re making bids to entertain, connect, etc. Your job as the listener is to try to figure out what they want from you. Do they want empathy, support, or something else? We often miss what others want.

To learn what people want, we ask open questions to invite more information.There are better and worse questions. You want to ask questions that reveal something about the person – their feelings, or who they are. “What’s your take on that?”

How do the 6 Core skills of Radical Listening help us communicate better with others?

The overarching thing to do is listen with positive intent and to understand the other person better. The first three core skills are internal and the next three are external. 

The six skills are:

  1. Noticing 
  2. Quieting your inner chatter
  3. Acceptance: even without similarities, try to accept the other person’s point of view
  4. Acknowledging: say something about what you’ve noticed
  5. Questioning: asking open questions
  6. Interrupting: You can either take turns talking, or you can jump in with a ‘wow’ or ‘me too’, which are interruptions which return the focus on the speaker.

What are two obstacles to radical listening?

Comparing and competing are two obstacles to listening well. Competing would look like trying to outdo the other person. Comparing is a cousin to that. For example, you share that you studied abroad. And the other person says, “I studied abroad, too! Here’s what my experience was like.” It’s disconnecting.

How can we effectively overcome those barriers to better approach our conversations?

Any time you’re listening with intention, knowing what you want to accomplish, you’re more likely to hear the emotional tone, the themes of what you’re saying. And if you’re the speaker, be clear about what you’re looking for.

What are your final words of advice for anyone who wants to go on their last first date?

Begin with a positive intention – listen with respect and ask great questions to learn about someone, and also be willing to give of yourself. Think about the times you were deeply listened to – how did it feel? Go do that!

Connect with Robert

Watch on YouTube


Please subscribe/rate and review the podcast here.

Apply to get FREE coaching on the podcast: https://bit.ly/LFDradiocoaching 

If you’re feeling stuck in dating and relationships and would like to finally find love, sign up for a complimentary 45-minute love breakthrough session with Sandy https://lastfirstdate.com/application

Join Your Last First Date on Facebook https://facebook.com/groups/yourlastfirstdate

Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life