Tag Archive for: Clara for Daters

Dates & Mates podcast listener success story finding untraditional love. New Years resolutions for your love life

Minisode: A Dates & Mates Love Story

Greetings, Happy Holidays, and a warm welcome to all the new listeners joining Dates & Mates from Excuse My Grandma, The Angry Therapist, Lovers & Friends, and more! In this special minisode, Damona has a delightful treat lined up.

For anyone who felt Santa’s deliveries were missing that extra touch of love, worry not! Damona has an inspiring story to share that will fuel your romantic journey. Joining the show is a fantastic guest, ready to unveil a love story woven into the fabric of Dates & Mates.

And stay tuned till the end for quick, actionable advice on creating a New Year’s resolution for love.

ROBIN (2:30)

Today, the focus is on the remarkable love journey of our guest, Robin, who discovered dating success by implementing advice from “Dates and Mates.” Robin’s story serves as a testament to the potency of setting clear goals and values while seeking a partner. 

(3:33) The Power of Clarity and Communication 

Robin shares her love story and how Dates and Mates played a significant role in her journey. Robin highlights the importance of clear communication and setting shared goals and values in a relationship. She mentions how she applied the advice from the podcast, such as getting off dating apps and focusing on building communication through phone calls. Robin also emphasizes the significance of prioritizing how someone treats you over external factors like income or profession. “I remember the shared goals and values that really registered with me and making sure that I was identifying those as early on as possible in dating.” 

(7:03) Navigating Nontraditional Romance

Robin’s love story takes a nontraditional path, as she met her current partner on a dating app after freezing her eggs. Despite societal expectations, Robin and her partner decided that marriage wasn’t their immediate focus. Instead, they prioritized milestones like buying a house and starting a family. Robin’s story challenges the notion of traditional relationship milestones. 

(9:40) Overcoming Challenges and Finding Love

Robin shares her experience of navigating challenges in her dating journey. After a challenging breakup, she took time to reflect on her goals, values, and the lessons she learned. “The breakup was devastating for me. I thought that I was with my person. And I told myself there are three things I want to be sure of before I start dating again.”  She emphasizes the importance of being clear about what you want and not settling for someone who is ambivalent or unsure. Robin’s story shows that when you do the work and have clarity, you can quickly align with the right person. 

 (16:05) Making Your New Year’s Resolution for Love Come True 

Damona provides three tips for making your New Year’s resolution for love a reality:

  1. Write down your goals and visualize them daily.
  2. Share your resolution with a friend or support system to hold you accountable. 
  3. Seek guidance and using available resources, such as her book “F the Fairy Tale,” to navigate the dating process more effectively. Damona’s tips empower individuals to approach dating with clarity and intention in the new year.

As always you can submit your questions for Dear Damona on Instagram, X, TikTok or Facebook and hear our answers live on the show! 

Dates & Mates podcast interview with Paul Keable from Ashley Madison about Gen Z joining the app

Decoding Gen Z & Financial Secrets

It’s no question that with every generation the world of dating evolves and changes. Sociologists say baby boomers enjoyed the sexual revolution, Gen X experienced an individualized dating experience, Millennials launched us into the era of online dating, and now Gen Z are really taking things to the next level. From LAT relationships to being monogamish,  Gen Z is looking for relationships that fit their needs while encouraging their growth.

And here to discuss it all with Damona is Paul Keable, the Chief Strategy Officer for Ashley Madison, the world’s leading married dating website.

Now we know what many of you are thinking – “Ashley Madison?! I am looking for a single partner!” And we get it! We are not here to encourage infidelity, but we are here to learn! 

The team over at Ashley Madison has been hard at work compiling invaluable data about its users. So Paul joins us to break down the company’s recently published study, “Decoding Gen Z: A global report on non-monogamy, sex, and the desire for discretion”. 

Dating Dish (2:39)

But first, we have the dating dish and WalletHub’s Financial Secrets Survey reveals intriguing insights:

WalletHub’s latest survey exposes the hidden truths people hold about money in their partnerships. From who’s more secretive to the generational honesty divide, the data is eye-opening. 

Did you know 76% more men harbor financial secrets than women? And surprise, baby boomers top the charts for honesty. But here’s the kicker: nearly one in four people believe their partners don’t deserve financial transparency. 

Yet, as Damona explores, these secrets aren’t just about money—they’re often a stand-in for deeper issues, impacting communication and trust. With 17% unwilling to forgive financial deceit, she challenges us to rethink the risks of hiding financial truths in relationships. There’s more to uncover in this insightful WalletHub study—tune in for the full scoop!

Paul Keable (7:45)

Paul Keable, the Chief Strategy Officer at Ashley Madison, joins the conversation to discuss the company’s recent study on Gen Z relationships and dating. With over seven years of experience at Ashley Madison, Paul sheds light on intriguing insights about the dynamics of relationships among the younger generation. 

(09:46) The Evolution of Ashley Madison and Its Appeal to Gen Z 

Paul Keable shares the evolution of Ashley Madison, which was born in the early 2000s when traditional dating sites like EHarmony and Match were grappling with married individuals pretending to be single on their platforms. The founders of Ashley Madison saw an opportunity to create a space specifically for married people looking to have affairs.

Since its launch in 2001, Ashley Madison has grown to over 80 million members, with a significant portion being Gen Z. Paul believes this is because Gen Z values the discretion that Ashley Madison offers. He also mentions that Gen Z has a greater awareness and acceptance of their own sexuality and sexual activities. He says they no longer feel the same pressures and shame associated with sex that previous generations experienced.

 (13:43) The Changing Dynamics of Relationships

Paul and Damona delve into the changing dynamics of relationships and the unrealistic expectations placed on one person to fulfill all roles in a partnership. Paul explains how Ashley Madison provides a space for individuals to be more honest and open about who they are and what they want in relationships. Damona asks Paul why platonic relationships can’t fulfill those other relationship needs.

The episode also touches on the trend of non-monogamous relationships among Gen Z daters. Paul mentions that 56% of Gen Z individuals surveyed expressed interest in non-monogamy. This reflects a shift in the definition of partnership, where individuals seek multiple partners who fulfill different aspects of their personality and interests. “This doesn’t boil down to just getting in the bedroom and having sex every other day with ten different partners… a far greater portion of people are just saying I want to have a level of intimacy, a connection with people that suit different parts of my personality.

(28:33) The Role of Ashley Madison in Exploring Desires

Paul emphasizes that Ashley Madison is not for people in happy monogamous relationships but rather for those who are seeking emotional validation or are not satisfied sexually in their current relationships. 

He challenges the stereotype that men cheat solely for sexual desire, stating that many men on Ashley Madison seek emotional validation. 

On the other hand, women on the site are often looking for good sex and orgasms that they are not getting from their partners. “80% of the women who came to Ashley Madison said they were there because they were in a sexless or orgasm-less marriage, and you know that really holds true when I speak to my members.”

Read the full Ashley Madison study, “Decoding Gen Z: A global report on non-monogamy, sex, and the desire for discretion”, yourself by visiting ashleymadison.com/insights

Dear Damona (40:34)

Submit your questions on Instagram, X, TikTok or Facebook and hear our answers live on the show!

  • IG Message from Molly: Hi Damona! I broke up with my ex 10 months ago because of a lot of issues within the relationship. He was a nice person but the puzzle pieces did not fit well for us. I guess for me I am having trouble “letting go/moving on completely”. I have gone on a few dates this year but question if this other person is someone whom I want to build a life with for the next 40 years? How do I move on from my ex?


Dear Damona: Much Younger Match & Saying I Love You

The questions have been pouring in and so we are doing an all-Dear Damona episode of Dates & Mates today! Time to ease your minds and get you back on track for love in the new year.

In case you’re new here, our podcast episodes typically happen in three parts – headlines of the week, interviews, and a Dear Damona Q&A segment but we love shaking things up! It’s always to help you understand yourself and handle the ups and downs of modern dating.


If that resonates, be sure to pick up a copy of Damona’s new book, F the Fairy Tale, out January 2nd! Enter our pre-order giveaway at DamonaHoffman.com/giveaway for a chance to win two VIP tickets to The Drew Barrymore Show, a $500 travel voucher, and a $500 shopping spree at Democracy Clothing. 

damona hoffman f the fairy tale book giveaway drew barrymore show

Now…let’s get to these questions!

Dear Damona (3:22)

03:27 IG DM from Aaron

Hi Damona, I started dating someone just under two months ago. It’s going well; the conversation flows. I feel secure and calm when we are together. He told me he loves me a little over a month in. Is that too fast? I’m pretty inexperienced with long-term relationships. How should I know when to say “I love you”?

7:02 Voice memo from V

Hi, Damona. I’m a big fan of your show. Thank you for everything that you do. It’s been so helpful. I do have a question. I’m wondering if you have advice for the ladies out there who are the ones being engaging, keeping a conversation going, asking the questions, and doing the heavy lifting because it’s getting tiring. I find myself in this position. It’s frustrating that it feels like a lot of guys I match with don’t know how to pass that ball back and forth in a conversation. It feels like a dead end. And, frankly, I’m feeling so over it. So, I would love to know your thoughts on if I should just move on

15:57 Email from Montie

Dear Damona, I hope you know that you are my bestie (in my head)!!! You’ve always given such great advice; sister don’t fail me now; just shoot me straight! I’ve been divorced for 12 years, and while I’ve had a couple of significant relationships, nothing has ever stuck as my forever relationship. I’m currently seeing someone who is much younger (I’m 57; he’s 39…gulp!). We click, we vibe, and the relationship is relaxed and easy. We are monogamous, and he’s wanting a forever future with me (we’re approaching 4 months together). I adore him, but I often wonder if I’m excited about being off the market finally or if we really will fit long term! Help!! Or realize that this could just be one of my deal breakers? Honestly, the thought of dealing with it stresses me out.


21:48 DM Voice Memo from C:

Dear Damona, I’ve mentioned before that I’m dating in my 30s. And, you know, it’s a priority for me to have a family. I’ve been going on lots of dates. But yeah, I just have not found, honestly, anyone that I’ve been really excited about. There hasn’t really been any man who I’ve gone on more than four dates with. And, yeah, I mean, look, I have to say it’s always me who’s ending it. I’m really struggling, in all honesty, in finding men who are emotionally mature. Just what I consider a basic level of maturity is just so difficult to find for some reason. And so, and I think that’s partially contributing to my disillusionment. But yeah, if you have any tips for sourcing men who are more emotionally mature, that would be great. I’m open to it in real life. I’m open to online. I must be just looking in the wrong places. I don’t know. Thanks!!!

Have More Questions? (33:37)

Submit your questions on Instagram, X, TikTok or Facebook and hear our answers live on the show! 


Good Jealousy & Dating App Etiquette

As 2023 draws to a close and the holiday season approaches, you may be experiencing a wave of strong emotions. Perhaps you are introducing your loved ones to your new partner for the first time or fielding questions on why you remain blissfully single. Or you may be contemplating whether to take a relationship break and start fresh in the new year.

Whatever your situation, emotions can run high! That’s why today’s episode features an insightful chat with sex and relationship coach Dr. Tara. She’ll share her secrets to improving conflict resolution through empathetic listening. Dr. Tara will also reveal whether jealousy can play a constructive role in relationships. Additionally, she’ll discuss trends she expects to see in 2024, drawing from her extensive experience as a tenured professor of sexual and relational communication.

But first, this week’s spicy Dating Dish explores the latest dating app etiquette trends you can’t miss.The Dear Damona question is: How do I get my boyfriend to be honest with me? Let’s get started!



It’s the giving season, and with all your time spent on others, now is the time to give back to you. For those who pre-order the January-releasing book “F The Fairytale,” our exciting giveaway offers prizes like two VIP Drew Barrymore Show tickets in NYC plus $500 shopping/travel vouchers. Over 30 runners-up can win a 3-month OkCupid Premium membership.

Our publishers. Seal Press and Hachette,  are calling this their biggest book giveaway yet! Be sure to enter to win by preordering your copy today at DamonaHoffman.com/giveaway.


The New Dating App Etiquette

A Washington Post article featuring Damona outlines the new dating app etiquette:

  1. Keep profiles light and fun
  2. Send a real message
  3. Create momentum
  4. Share how you like to communicate
  5. No therapy in the DMs
  6. Pause before you post

Damona elaborates offering unique insights like her #1 ghosting alternative and how to confidently avoid the endless texting trap.


Coming up this Thursday, we’re hosting a virtual cocktail party with top dating experts to deconstruct fairy tale myths and provide pillars for the relationships you desire, whether dating or committed. Incredible authors like Catherine Woodward Thomas and love astrologer Carol Allen will join live panels inspired by Damona’s upcoming book “F the Fairytale.” For one night only, these legends, who rarely collaborate, will answer your questions to walk you into new love. Sign up free now at DamonaHoffman.com/forum to engage live or watch recordings later.

DR. TARA  (11:47)

Joining us today is award-winning sex researcher and Cal State Fullerton professor Dr. Tara, host of the “Luvbites” podcast. As a tenured expert on sexual and relational communication, author of “Sexual Communication Research in Action,” and resident sexpert on the British dating show “Celebs Go Dating,” Dr. Tara’s wisdom has been widely featured from Cosmo to PopSugar.


(14:35) The Younger Generation: What Do They Want to Know

College students ask Dr. Tara about alternatives to all-or-nothing monogamy versus complete openness, unaware of relational options between the extremes. Though craving lifelong partnership, Gen Z’s divorce exposure makes them wary, hence the interest in primarily monogamous bonds with some flexibility to periodically push boundaries. “In class, we have a whole unit on relational structures where we talk about different ways you can be in a relationship, and their minds are blown because all they’ve heard is either completely open, polyamorous, or monogamous forever.

(18:36) Online Dating Trends and Predictions Going into 2024

Dr. Tara has observed much dating fatigue and choice overload on apps lately, but millions still use them. Looking ahead, she expects rising demand, especially among more mindful Gen Z users, for specialized matching based on compatibility and quality over sheer quantity. Compared to her 20s experience feeling overwhelmed by expansive possibilities on early apps like Tinder, Dr. Tara sees today’s focus shifting to self-care through intentional matching with better-suited potential partners.

(25:20) Conflict Resolution with SALLY

When fighting with your spouse, Dr. Tara advises remembering the “SALLY” method to facilitate conflict resolution: Slow down, Ask questions, Listen empathically, List wants, and Yes to doable actions while giving them the benefit of the doubt. Naturally, continued disrespect crosses boundaries, requiring a bigger conversation. But in one-off conflicts, this simple yet evergreen advice can work wonders.

(27:56) Empathetic Listening: Thinking Outside the Textbook

Dr. Tara suggests envisioning your partner as a five-year-old you aim to uplift with warmth and compassion. She proposes unarming yourself by letting go of resentment and judgment in order to deeply listen and connect. In her view, self-acceptance enables empathy for others. So Dr. Tara advocates nurturing self-care to hold space for struggles with empathy, thoughtfully questioning negativity rather than compromising dignity. Ultimately, she chooses empathy’s high road, for it can empower and uplift.

(30:39) Jealousy’s Not So Bad After All

Dr. Tara argues some jealousy can be healthy, revealing care in a relationship. She distinguishes bad explosive jealousy from good jealousy, which opens constructive communication. In her view, everyone experiences innate jealousy to some degree – low self-esteem exaggerates it, while self-confidence lessens it. Ultimately though, she believes handled compassionately, jealousy has the power to foster greater intimacy.

Follow Dr. Tara on Instagram
@luvbites.co and check out her podcast, Lovebites with Dr. Tara, wherever you listen to Dates & Mates!




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

    • Email from K: How do I get my boyfriend to be honest with me?

Animal Attraction & Love Abroad

Welcome to Damona’s BIRTHDAY WEEK episode on Dates & Mates! 

After celebrating another journey around the sun, Damona has been reflecting on the life path she has forged. She remembers that inner love cynic who cast doubts on her dreams of an amazing partner, a fulfilling career, and a happy family. This week she shares how that skeptic once served a purpose in protecting her heart, but how she came to a point in time when she had to bid those doubts farewell. We know many of you have similar cynics holding you back—that’s why you tune in. 

Damona’s birthday wish? For you to shed those doubts and craft your own love story. 

Her new book ‘F the Fairy Tale’ serves as a roadmap for this journey, and the biggest gift you could give Damona is pre-ordering the book at FTheFairyTaleBook.com and sharing how it empowered you in the new year.

And to further empower you, we will be joined this week by esteemed guest, Dr. Wednesday Martin. She joins us to illuminate the evolving landscape of female sexuality within this dating jungle. Her expertise in cultural studies, anthropology, and psychology promises to expand our understanding of how our primal instincts adapt in this new normal while maintaining connections and passion. 

We also bring back the Dating Dish and finish up with another amazing question from a listener in Dear Damona! Let’s get started!!


Get ready for an eye-opening look into 2024’s dating scene straight from Bumble’s recent survey of over 25,000 users! Uncover the shift in age preferences, the newfound importance of shared political views, and the rising allure of mindfulness in relationships.


And check out our episode with matchmaker and dating & relationship coach, Rachel Russo, titled “Age Gap Crap & Solo Mom” for more on the shift around age and dating.


Dr. Wednesday Martin joined us with a background spanning anthropology at the University of Michigan to a doctorate in comparative literature and cultural studies from Yale. Her accolades include becoming an instant New York Times bestseller with ‘Primates of Park Avenue’ and her recent groundbreaking book ‘Untrue: Why Nearly Everything We Believe About Women, Lust, and Infidelity Is Wrong and How the New Science Can Set Us Free’. 

Her insightful writing covers gender, parenting, motherhood, and female sexuality for renowned publications like The New York Times, The Atlantic, and Harper’s Bazaar. With appearances on major networks like CNN, NPR, and NBC News, Dr. Martin’s expertise is second to none.

(13:43) A Dating Evolution

Dr. Wednesday digs into the lightning-speed changes tech brings to dating. She highlights the clash: our longing for connection versus the surge in app-based dating post-COVID’s upheaval. 

“We had a big collective trauma, whether we processed it that way or not. We are still reeling and recovering as a dating and mating species. And, we’re adjusting to a whole new ecological niche, which is swipe culture.”

She underscores our innate drive to connect, even digitally, sparking those feel-good vibes.

(15:35) Are Dating Apps Going Away?

Dr. Wednesday brings a positive spin to dating apps, seeing them as this new world we’re getting used to, and they’re not going anywhere! She appreciates how they kept us connected during tough times, feeding our need to reach out. 

She cheers for how these apps let women and everyone else be clear about what they’re after, making space for everyone’s desires. But she also nods to the grumbles we often hear about these apps, acknowledging that despite their perks, dissatisfaction can sometimes remain. “We can develop a dating ecology, but we can’t determine how people use it”.

(23:15) Reality of the Dating Desert

Dr. Wednesday delves into the challenges faced by heterosexual women in today’s dating scene, referring to it as a “dating desert.” She says, “So what we find is that in most big cities, men are the limiting sex. So men have the power in dating because there are fewer of them relative to women.”

She points out how cultural norms around emotional expression create a disconnect between men and women, affecting their connection in relationships.Her insights offer a window into why women, encouraged for emotional intelligence, might find it hard to connect with men raised to suppress emotions. This mismatch in emotional expression, she notes, shapes the dating landscape, making it tough for women seeking aligned connections.

(36:36) Construct an Ecology in a Dating Desert

Dr. Wednesday delves into crafting unique dating spaces within the dating landscape, likening them to finding oases in a desert. Exploring environments where gender ratios align with preferences is key, particularly in heterosexual scenarios where women often hold sway. 

Reflecting on our innate attraction to novelty, she suggests venturing into new social circles for fresh connections. Ultimately, she champions authentic connections, urging individuals to break societal norms for personal happiness in dating.


Follow Dr. Wednesday on Instagram @WednesdayMartinPHD and grab a copy of her book, “Untrue: Why Nearly Everything We Believe About Women, Lust, and Infidelity Is Wrong and How the New Science Can Set Us Free”.




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

  • Email from Caroline – Can you be a committed dater when you are an adventure seeker and or may be moving?

Measuring Matches & Return to Singlehood

In a fast-paced digital age, finding genuine connections can sometimes feel like searching for a needle in a haystack, but could the antidote to your trouble be to lean in, even when you feel like throwing in the towel and date with more intention?

That’s why the word of the week is CLARITY.

Finding love may seem unpredictable to some. “I’ll know it when I see it,” people say. But we call BS on leaving love to chance alone. After 17 years of coaching and writing dating profiles, Damona is convinced intentionality is key to romantic success. To be intentional, you first need clarity – a focused mindset. 

We talk A LOT about intentionality on the podcast and have given some examples in the past of ways to log and analyze your dating data from stat sheets to journaling. Today we are going to introduce ANOTHER way to understand and track what’s really happening in your love life so you can chart your way to the relationship you want.


Jillian Romero Chaves was a successful automotive industry professional whose experience with a devastating breakup led to a journey of learning, healing and reflecting.

Motivated by her personal experiences, she channeled her passion into creating Clara for Daters, an intentional dating journal app designed to empower individuals to make informed choices and nurture healthy relationships.

(4:20) Clara for Daters is born!

After investing ten years with a cheating partner she had hoped to marry, Jillian Romero Chaves created the reflective journaling app Clara for Daters to empower single people to date more intentionally based on her own experience. 

Motivated by heartbreak, Jillian researched attachment styles and realized she lacked dating self-awareness, often letting attraction cloud her judgment. She designed Clara for Daters with the help of psychologists and experts to help singles be conscious about their relationship choices by tracking insights over time. This provides a framework for singles to learn from the past, take control of their love lives, and build healthy partnerships.

(10:40) Intentionality is key in dating

Jillian explains that Clara for Daters helps singles embrace a slow, intentional approach to dating even when they feel anxious and want a relationship right away. She acknowledges that at 35, her desire to marry and have kids makes it hard to act patiently. But the app allows her to track her dates so she feels closer to her goals, even without the outcome. Jillian says that just because you haven’t met the right person yet doesn’t mean you aren’t getting closer. 

(12:18) Let’s get technical about dating

Jillian describes the scores in the Clara for Daters app as deliverables that show progress. By logging dates and answering questions, you get closer to understanding what you want. “ I can’t hold that person that I’m going to be with in my hand yet. But I can hold this one deliverable, I can come back, refer to Clara, and see that I’ve been logging the dates, and I’m getting closer to understanding what I’m looking for and who that person is.” 

When reflecting on a date, the app often asks yes or no questions, then provides a space for notes. For Jillian, it asked if she found a certain date’s eyes attractive. She had had previous reservations, but said yes to this question. When she began elaborating in the notes section, she realized she had taken his expressive eyes for granted. This process of calling things out and reflecting intentionally builds attraction and self-awareness. 


(20.01) Can an app shift your values and intentions about dating?

Jillian explains that going through a difficult breakup and then intentionally reflecting on her patterns with Clara has absolutely shifted her values and intentions in dating. She realized her attraction to her “bad boy” ex was actually based on unhealthy patterns from her past, like people pleasing and trying to perform to keep him happy. It wasn’t real chemistry.

(24:22) Roster Dating 

Jillian explains that “roster dating”, or dating multiple people at once, and using the Clara app to log each date has helped reduce her anxiety and the pressure she feels for a date to work out. 

(26:53) How can we put the loneliness epidemic behind us?

Jillian advises viewing dates as opportunities for social connection which benefit mental health. “So then getting a relationship is not the outcome. It’s me exercising my social connection ability.” Just interacting with new people and avoiding isolation is a win with the loneliness epidemic. Even lackluster dates exercise social skills.

Jillian sees many inconsistent daters endlessly deleting and redownloading apps. She recommends staying consistent but focusing on self-improvement metrics. Define success by getting stronger at identifying what you want, building boundaries, learning your attraction levels – not forcing a partnership. Strengthening your relationship skills is the real “win.”
Be sure to follow Jillian on Instagram @jillianromerochaves and check out the Clara for Daters App!



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

  • Email from Marsha – Hi, Damona. I’m a 67 year old African American woman who hasn’t dated in seven years, the idea of putting myself out there is doubt and anxiety producing. I’m a totally different person now than I was seven years ago. Is there hope for me?