Laura Stassi, author and host of the Dating While Gray podcast, reveals how many of our dating challenges and solutions remain the same, regardless of age, gender, or sexuality. And Laura joins Damona for a special Dear Damona segment to answer your questions, like:

• I’d like to move to Tennessee and meet a Southern gentleman. Should I start dating long distance in the meantime?
• I have a medical issue that is lowering my self esteem. How can I move past this and begin dating again?

Listen to the Dating While Gray podcast wherever you get your podcasts and be sure to follow Laura on Instagram @DatingWhileGray

Ready to break free of your dating loops? Get Damona’s signature online program, The Dating Accelerator by visiting: DamonaHoffman.com/program

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

TIMESTAMPS

Introduction to the Episode (00:00:00)  

Guest Introduction (00:01:15)  

Laura's Background (00:02:19)  

Podcast Journey (00:05:41)  

Media Representation of Older Daters (00:06:21)  

Dating Trends and Challenges (00:10:34)  

Dating Attitudes Across Ages (00:11:57)  

Learning from Dating Experiences (00:14:04)  

Shifting Dating Etiquette (00:15:38)  

The rigidity of dating (00:16:16)  

Compromise in dating (00:17:22)  

Dating models and etiquette (00:18:36)  

Older daters' routines (00:19:47)  

Generosity in dating (00:20:46)  

Communication in dating (00:22:12)  

Meeting people offline (00:24:52)  

Overcoming fear of being alone (00:27:57)  

Reconnecting with past acquaintances (00:29:00)  

Long-distance dating considerations (00:31:01)  

Exploring Relocation for Love (00:31:59)  

Importance of Community (00:32:21)  

Dating as Discovery (00:34:13)  

Listener Question on Self-Esteem (00:36:20)  

Vulnerability in Sharing Challenges (00:37:26)  

Stigmas Around Health Issues (00:39:46)  

Navigating Disclosure in Dating (00:40:57)  

Redefining Sexual Intimacy (00:42:28)  

Intentional Dating Post-Pandemic (00:44:01)  

Comfort with Oneself (00:45:18)  

Closing Remarks and Resources (00:46:14)  

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Aleeza Ben Shalom, celebrity matchmaker of Netflix’s Jewish Matchmaking, shares actionable advice to help you find your path on this dating journey with wisdom from her new book “Matchmaker, Matchmaker: Find Me a Love That Lasts”. And the Dear Damona question this week is: What are the signs that someone is interested in you?

Pre-order your copy of Aleeza's new book, “Matchmaker, Matchmaker: Find Me a Love That Lasts”, by visiting: https://marriagemindedmentor.com/book/

And, follow Aleeza on Instagram @AleezaBenShalom!

Ready to break free of your dating loops? Get Damona’s signature online program, The Dating Accelerator by visiting: DamonaHoffman.com/program

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

TIMESTAMPS

Intro (00:00:00)  

Finding your personal dating playbook (00:01:03)  

Meet Aleeza Ben Shalom (00:02:14)  

Aleeza's journey as a matchmaker (00:02:50)  

Date them till you hate them (00:04:02)  

The three-date rule (00:05:30)  

Clarity in dating decisions (00:06:37)  

The importance of staying curious (00:07:25)  

Navigating difficult conversations (00:10:30)  

Rejection as a form of protection (00:13:20)  

The five-day challenge (00:14:42)  

Five Day Challenge Explained (00:15:04)

Clarifying the No Touching Rule (00:15:49)

Tips for the Challenge (00:16:36)

Importance of Connection in Dating (00:18:39)

Dating Dynamics and Tests (00:19:47)

Rules for Same-Sex Couples (00:20:33)

Calculating Relationship Compatibility (00:21:06)

Interests vs. Core Values (00:22:44)

Significance of Family Values (00:24:22)

Understanding Timelines in Relationships (00:26:53)

Self-Discovery in Dating (00:29:16)

The Five-Year Relationship Evolution (00:29:50)  

The 555 Dating Rule Explained (00:30:23)  

Building Momentum in Dating (00:31:04)  

Chemistry and Intentional Dating (00:34:13)  

Soulmate Clarity Concept (00:37:38)  

Navigating Workplace Relationships (00:40:41)  

Dating Gestures and Vibes (00:45:35)  

Small Moves in Dating (00:46:29)  

Attraction Beyond Age (00:47:22)  

Investing in Clear Signals (00:48:52)  

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This week’s episode is dedicated to YOU! The holidays are here, bringing all the cozy vibes, family gatherings, and… yep, those inevitable relationship questions. Damona answers all your pressing holiday love questions, from family expectations to finding romance under the mistletoe.She will answer your top questions like:

• I have been dating a wonderful man for 7 months now and STILL don’t feel a physical connection. Is it time to call it quits?
• I got ghosted after 4 months of dating, is it something I said?
• I am interested in some of the singles in my triathlon club. Do I shoot my shot or is it too risky?
• She made the reservation but then asked for my credit card to reimburse her the deposit. Is that a petty red flag?

Ready to break free of your dating loops? Get Damona’s signature online program, The Dating Accelerator by visiting: DamonaHoffman.com/program

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

TIMESTAMPS

Intro (00:00:00)  

Uncertainty in Relationships (00:00:01)  

Light-hearted Commentary (00:00:03)  

Holiday Dating Dilemmas (00:00:06)  

Listener's Voice Memo (00:01:55)  

Annie's Relationship Concerns (00:02:01)  

Ghosting After Four Months (00:07:58)  

Communication Issues in Relationships (00:09:00)  

Conflict Resolution Advice (00:12:22)  

Triathlon Club Dating Dilemma (00:16:24)  

Breaking the Ice in a Club (00:16:46)  

The Benefits of Physical Activity (00:17:18)  

Navigating Group Dynamics (00:19:50)  

Using Dating Apps (00:22:02)  

Addressing Gender Roles in Dating (00:23:55)  

Finding Common Ground (00:26:12)  

Preparing for Holiday Conversations (00:29:38)  

Closing Thoughts and Future Episodes (00:30:52) 

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Lauren Frances, Love and Relationships Expert, talks all about first dates from when they start (it’s not when you think) to how to graciously end one that’s just not working for you. And our Dear Damona question of the week is, “My match is great, not a single dealbreaker, and I STILL can’t wrap my head around commitment. What now?”

Want to join Lauren’s incredible Love Magnet Makeover? Just visit DamonaHoffman.com/lovemagnet

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

Timestamps

Intro (00:00:00)  

The First Date Starts Early (00:00:09)  

Preparation for First Dates (00:00:14)  

Value of First Dates (00:01:05)  

Introducing Lauren Francis (00:02:05)  

Persistence in Publishing (00:03:09)  

Timing in Dating (00:04:38)  

Transitioning to Phone Calls (00:05:53)  

Setting Up Phone Conversations (00:07:25)  

Importance of Privacy (00:09:10)  

Breaking the Ice (00:11:21)  

Choosing the Right Date Venue (00:12:18)  

Being Seen on Dates (00:13:06)  

Creating the Right Vibe (00:15:02)  

Understanding Enthusiasm in Dating (00:16:35)  

The Enthusiasm Gap (00:20:37)  

First Dates as Your Party (00:21:37)  

Heartache Prevention Tips (00:25:12)  

Compatibility and Actions Over Words (00:30:07)  

Ghosting and Relationship Alignment (00:31:02)  

Rejection Reasons (00:32:58)  

Ending Dates Positively (00:34:04)  

Creating a Great First Impression (00:35:02)  

Love Magnet Makeover Introduction (00:36:01)  

Details of Love Magnet Makeover (00:37:04)  

A Listener's Commitment Question (00:40:04)  

Navigating Relationship Fears (00:41:07)  

Understanding Commitment (00:42:19)  

Empowerment in Relationships (00:48:00)

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Dr. Alfiee, psychologist, host of the Couched in Color podcast and founder of the AAKOMA Project, dives into attachment styles, how depression can impact a partnership, and the ways our traumas and triggers can become unearthed in new relationships. Then this week’s Dear Damona question is: I married too young and stayed too long. Can you please help me get back into the dating game?

Ready to break free of your dating loops? Get Damona’s signature online program, The Dating Accelerator by visiting: DamonaHoffman.com/program

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

Timestamps

Introduction to the Episode (00:00:00)  

Attachment Styles Overview (00:00:59)  

Expectations in Relationships (00:03:30)  

The Desire to Change Partners (00:05:04)  

The Fantasy of Relationships (00:06:13)  

Effort vs. Work in Relationships (00:08:01)  

Unpacking Emotional Baggage (00:08:35)  

Understanding Attachment Styles (00:09:55)  

Cultural Context of Attachment (00:12:04)  

Personal Experiences with Attachment (00:14:23)  

Embracing Attachment Nuances (00:15:17)  

Understanding Family Dynamics and Attachment Styles (00:16:50)  

Personal Reflection on Attachment Styles (00:17:42)  

The Impact of Community on Relationships (00:18:26)  

Navigating Triggers in Relationships (00:19:55)  

Mental Health and Medication Statistics (00:20:37)  

Stigma Around Mental Health in Communities (00:22:13)  

Dating with Mental Health Challenges (00:23:05)  

Recognizing Deal Breakers in Relationships (00:23:43)  

Changing Attitudes Towards Therapy (00:25:51)  

Generational Differences in Mental Health Views (00:27:06)  

Healing from Trauma and Relationships (00:28:08)  

The Process of Healing and Trauma Management (00:30:25)  

Distinguishing Good and Bad Butterflies (00:32:22)  

The Importance of Self-Reflection Before Dating (00:33:14)  

Understanding Triggers in Relationships (00:33:50)

Disclosing Trauma in Relationships (00:35:17)

Trust and Safety in Sharing Trauma (00:36:12)

Empowerment in Relationships (00:38:17)

Unpopular Opinions on Relationships (00:39:46)

Finding a New Relationship After Marriage (00:41:23)

Going Where the People Are (00:43:24)

Strategic Socializing for Dating (00:45:38).

Creating Momentum in Dating (00:49:04)

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Whether you’re navigating cuffing season, gearing up to meet someone's family for the holidays, or figuring out how to take your dating game to the next level— Damona dedicates this week’s episode to YOU! She’s answering your toughest Dear Damona questions, like:

• I struggle to find matches in my area and while I am willing to travel, many men aren’t. So what now?
• My matches keep removing their profiles once we exchange numbers. What’s going on here?
• When should daters consider sleeping together?
• Are gender roles changing or do men still have to be the initiator?

Find Damona and submit your questions on any of the socials @DamonaHoffman or by visiting her website DamonaHoffman.com/contact

Bad news…we filled our last spot for the year. 

Good news!! We opened ONE BONUS for VIP coaching this fall. Last chance to get one on one coaching with Damona and her team. Want to snag our lucky last spot? Register for an intro call at DamonaHoffman.com/introcall asap!

TIMESTAMPS

Intro (00:00:00)

Does This Mean He Likes Me? (00:00:01)

Am I Ever Gonna Meet Someone? (00:00:04)

I'm Tired of Swiping (00:00:06)

Cuffing Season and Relationship Dynamics (00:00:08)

Adrian's Dating App Dilemma (00:01:43)

Changing Location Filters in Dating (00:04:25)

The Importance of Compatibility (00:05:39)

Long-Distance Relationship Insights (00:06:53)

Dating Apps and Long-Distance Features (00:09:24)

Caution Against Exchanging Phone Numbers (00:11:28)

Identifying Catfish and Scammers (00:12:38)

Maintaining Momentum in Communication (00:13:38)

Sue's Experience with Catfish (00:14:41)

Navigating Online Dating Safely (00:15:54)

Introduction to Possible Soulmates (00:17:59)

Guidelines for Intimacy (00:19:01)

Understanding Sexual Health (00:20:22)

Pacing Your Relationship (00:24:23)

Women Initiating Dates (00:25:28)

Mutual Interest in Dating (00:26:46)

Being True to Yourself (00:29:04)

Closing Remarks and Engagement (00:30:19)

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Esther Lee, Deputy Editor of The Knot, breaks down the stats released in the website’s Relationship & Intimacy Study, and spills the tea on where singles are finding love, what they’re actually looking for, how they’re spending their time on dates, and those dating dealbreakers we just can’t shake. And, this week’s Dear Damona question is: Is a bra an appropriate gift for a young couple?

Ready to break free of your dating loops? Get Damona’s signature online program, The Dating Accelerator at 10% off (for limited time only) using the code PODCAST10: DamonaHoffman.com/program

LAST CALL - Just 1 spot remains for the VIP one-on-one coaching program this year. Serious applicants should book an assessment call ASAP with our head of coaching programs: DamonaHoffman.com/introcall

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

Timestamps

Introduction to the Episode (00:00:00)

Damona's Welcome (00:00:13)

Introducing Esther Lee (00:01:04)

Damona's Personal Wedding Experience (00:02:11)

Evolution of Wedding Planning (00:02:49)

The Knot's 2024 Study Overview (00:03:46)

Key Findings of the Study (00:05:01)

Dating Apps vs. Real-Life Connections (00:05:54)

Generational Perspectives on Dating (00:06:41)

Changing Standards in Attraction (00:07:56)

Being Easy to Talk To (00:09:14)

Fostering Connection and Communication (00:09:47)

Listening as a Key Element (00:11:40)

The Chemistry Myth (00:12:10)

Importance of Sexual Attraction (00:12:59)

Married Couples and Sexual Chemistry (00:14:00)

Comfort and Chemistry in Relationships (00:15:54)

Commitment After Marriage (00:16:51)

Importance of Attraction (00:18:05)

Subjective Sense of Humor (00:19:29)

Humor as Relationship Tool (00:21:01)

Video Game Dates (00:21:48)

Meeting Through Gaming (00:24:00)

Creative and Affordable Dates (00:26:06)

Deal Breakers in Relationships (00:29:59)

Chemistry vs. Values (00:31:00)

Long Distance Relationships (00:32:48)

Communication in Long-Distance Relationships (00:33:14)

Intentionality in Relationships (00:34:05)

Finding Love Beyond Geography (00:35:36)

Unpopular Opinion on First Dates (00:37:17)

Navigating Intimate Gift Missteps (00:39:20)

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Benjamin Camras, The Flirt Coach & host of the Flirtations Flirtcast, joins Damona for our annual Halloween Dating Horror Stories Special. You’ll laugh, you’ll scream, and you’ll get useful advice to survive your next bad date. Stories include:

• Blindsided by a Blind Date
• The Vegetarian Variation
• The Creepy Car Concert
• The Deskside Date
• The Freudian Movie Man

Ready to break free of your dating loops? Get Damona’s signature online program, The Dating Accelerator at 10% off (for limited time only) using the code PODCAST10: DamonaHoffman.com/program

Only 1 spot remains for the VIP one-on-one coaching program this year. Serious applicants should book an assessment call ASAP with our head of coaching programs: DamonaHoffman.com/introcall

Submit your questions for Dear Damona on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

TIMESTAMPS

Introduction to Halloween Horror Stories (00:00:00)

Listener Engagement (00:00:07)

Benjamin the Flirt Coach Introduction (00:02:18)

Costume Reveal (00:02:30)

Personal Dating Horror Stories (00:04:10)

Listener Story from Amanda (00:07:07)

Discussion on Movie Dates (00:11:40)

Activity Date Preferences (00:12:40)

Candy Smuggling at the Movies (00:14:31)

Vegetarian Red Flag Story (00:15:47)

Flirty Late Night Snack Decisions (00:16:31)

Libras and Perspective (00:17:09)

Boundaries and Alcohol-Induced Choices (00:19:20)

Dating an Older Guy (00:20:01)

Red Flags in Dating (00:21:11)

Avoiding Generalizations in Dating (00:22:13)

First Date Conversations (00:24:49)

Exploring Physical Intimacy (00:26:11)

Flirtation as Foreplay (00:27:28)

Listener Horror Story Introduction (00:28:44)

Zoom Date Disaster (00:30:24)

Multitasking on Dates (00:31:57)

Check-in Date Tips (00:33:04)

Pre-Date Communication (00:33:50)

Slow Dating Trend (00:34:13)

In-App Calling Features (00:37:13)

Age and Dating Preferences (00:38:28)

Horror Story Introduction (00:39:55)

Uncomfortable Date Behavior (00:41:32)

Lying About Height (00:43:01)

Closing Remarks (00:46:18)

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Erika Wasserman, Your Financial Therapist, is shifting the narrative around money and using those sometimes-tough conversations to build deeper trust and better communication with your partner and tackling the tricky financial situations singles often find themselves in while dating. Our Dear Damona question this week is: I have social anxiety. Do I need to focus on making more friends before pursuing a romantic relationship?

Ready to break free of your dating loops? Get Damona’s signature online program, The Dating Accelerator at 10% off (for limited time only) using the code PODCAST10: DamonaHoffman.com/program

Only 2 spots remain for the VIP one-on-one coaching program this year. Serious applicants should book an assessment call ASAP with our head of coaching programs: DamonaHoffman.com/introcall

Submit your questions on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

TIMESTAMPS

Introduction to Relationship Stress (00:00:00)

Host's Opening Remarks (00:00:14)

Introduction of Erika Wasserman (00:02:26)

Erika's Journey to Financial Therapy (00:03:19)

Dating and Financial Transparency (00:04:08)

Challenges of Financial Conversations (00:09:15)

Gamifying Financial Discussions (00:10:01)

Reality of Debt in Dating (00:12:04)

Understanding Debt and Relationships (00:14:46)

Understanding Debt and Readiness to Date (00:15:46)

Differentiating Rich and Wealthy (00:17:32)

Wealth Beyond Money (00:19:51)

Influence of Family Background on Money Beliefs (00:21:20)

Communication About Money (00:22:40)

Fear of Financial Loss in Relationships (00:23:25)

Pricing Themselves Out of the Dating Pool (00:24:12)

Contributions in Relationships (00:25:35)

Navigating Different Financial Backgrounds (00:28:00)

Frugality vs. Spending Comfort (00:32:01)

Coupon Encounter (00:33:03)

Financial Conversations (00:34:06)

Creating Financial Intimacy (00:35:38)

Side-by-Side Conversations (00:36:27)

Vulnerability in Conversations (00:37:08)

Joyful Spending (00:38:38)

Unpopular Opinions (00:39:50)

Divorce Edition Cards (00:40:24)

Impact of Financial Relationships (00:40:55)

Listener Question on Social Anxiety (00:42:00)

Building Connections (00:44:38)

Taking Baby Steps (00:47:39)

Engaging with the Audience (00:48:42)

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Take a sneak peak into a private coaching session with our listener, Michelle, as Damona identifies the dating loops and myths that are keeping this Dates & Mates Method graduate from finding the relationship she desires. Listen in as Michelle comes to a realization about the men she’s been dating and why it hasn’t worked out. And help yourself along the way as Damona shares quick tips and takeaways that you can apply right away to your own dating dilemmas.

Ready to break free of your dating loops? Get Damona’s signature online program, The Dating Accelerator at 10% off (for limited time only) using the code PODCAST10: DamonaHoffman.com/program

Only 2 spots remain for the VIP one-on-one coaching program this year. Serious applicants should book an assessment call: DamonaHoffman.com/introcall

Submit your questions on any of the socials @DamonaHoffman or by visiting DamonaHoffman.com

TIMESTAMPS

Introduction to the Episode (00:00:00)

Coaching Insights (00:00:59)

Michelle's Experience (00:02:47)

Appreciation for Coaching (00:04:41)

Transformational Skills (00:05:50)

Dating While Pregnant (00:06:05)

Desire for Partnership (00:06:53)

Impact of Solo Parenting on Dating (00:08:47)

Understanding High Standards (00:10:15)

Trusting Oneself (00:11:00)

Freeing Yourself from Pressure (00:11:32)

Encouragement to Freeze Eggs (00:12:11)

Embracing Options in Dating (00:14:39)

Current Dating Life (00:15:26)

Effective Screening Process (00:16:15)

Invitation to Continue Conversation (00:17:13)

The Importance of Boundaries (00:18:11)

Mindset for Successful Conversations (00:18:27)

Challenges with Dating Separated Individuals (00:19:14)

Physical Attraction and Curiosity (00:20:23)

Recognizing Anxiety in Dating (00:21:20)

Discovering Availability Issues (00:21:40)

Misleading Profiles and Aliases (00:23:32)

Learning to Say No (00:24:38)

Exploring the Other Camp (00:25:07)

Signs of Attraction and Availability (00:26:05)

Disappointment in Dating Dynamics (00:27:17)

The Complexity of Attraction (00:28:19)

Nurturing vs. Romantic Dynamics (00:31:01)

Finding the Right Words (00:32:08)

Navigating Emotional Intensity (00:33:57)

Testing Attraction in Early Dates (00:35:12)

Belief and Self-Responsibility (00:37:02)

Inheriting Stories (00:37:50)

Rewriting Personal Narratives (00:39:14)

Mindset Shifts and Mantras (00:41:10)

Attraction Dynamics (00:43:10)

Navigating Dating While Parenting (00:46:07)

Reflection on Progress (00:48:21)

Encouragement and Support (00:51:07)

Coaching Transformation Invitation (00:52:14)

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Meghan Keane, the founder of NPR’s Life Kit, shares her new book, “Party of One: Be Your Own Best Partner”. Listen in as she peels back the layers of our complicated feelings about being single and dissects the ways that singlism could be dealt with in your own life. It’s time to embrace your single life or the singles in your life so that we can all thrive together regardless of our relationship status. Our Dear Damona question this week is: I recently reconnected with a casual long term friend. How do I figure out if he likes me without making a fool of myself?

Fun little announcement, my meditation program is now back on the Dates & Mates website. If you want to meditate and visualize your way out of stressing about your singlehood. Let me help you. Look for my meditation collection on the homepage of DamonaHoffman.com today!

Submit your questions on any of the socials @DamonaHoffman or by visiting her website DamonaHoffman.com

TIMESTAMPS

Introduction to Singlehood (00:00:00)

Embracing Singlehood (00:01:03)

Interview with Meghan Kane (00:02:54)

Navigating Societal Expectations (00:03:18).

Understanding Singleism (00:06:24)

Confronting Single Shame (00:09:30)

Transforming Thoughts: From Why to What (00:10:41)

The Power of Storytelling (00:14:50)

Intimidation in Dating (00:16:54)

The Complexity of Strong Women (00:17:01)

Reframing Intimidation (00:18:00)

Questioning Marriage (00:19:00)

Voyeurism in Dating (00:20:00)

Building Intentional Friendships (00:21:54)

Diversity in Friendships (00:22:36)

Making the First Move (00:23:15)

Finding Friends with Shared Values (00:24:56)

Lowering the Stakes in Friendships (00:25:50)

Digital Connections (00:27:18)

Mindset Shifts After Relationships (00:30:32)

Radical Acceptance in Singlehood (00:31:52)

Values Work and Radical Acceptance (00:33:01)

Life Values Inventory (00:34:04)

Building Goals Around Values (00:34:50)

Changing Scripts in Dating (00:36:35)

Unexpected Partnerships (00:37:25)

Maintaining Individuality in Relationships (00:38:53)

Supporting Single Friends (00:39:34)

Self-Work and Future Relationships (00:41:46)

Unpopular Opinion on Dating (00:42:14)

Understanding Dating Apps and Intentions (00:49:25)

Challenging Negative Narratives (00:50:23)

Creating Your Own Love Story (00:51:33)

Upcoming Episode Teaser (00:52:45)

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