Alyssa sits down with Francesca Hogi, love coach, founder of the True Love Society, two-time TED speaker, former corporate lawyer, and two-time Survivor contestant, for a conversation built around one deceptively simple idea: flirting is a skill, not a personality trait, and most of us were never taught it. Francesca breaks down her definition of flirting (words and actions that make someone feel seen, special, and acknowledged), why it has nothing to do with being “hit on,” and why she sees it as a foundational relationship skill rather than a prelude to dating.

The conversation ranges from Francesca’s path from Survivor contestant to matchmaker to coach, into genuinely useful, practical territory: the “puke test” for knowing when there’s truly no chemistry versus just none yet, why she tells clients rejection isn’t real, and how flirting can actually spark chemistry that wasn’t there on date one. Alyssa connects a lot of this directly to her own four-date-minimum philosophy, and the two get into what dating would look like if they could rebuild it from scratch, plus Francesca’s “meet cute mindset” challenge that’s genuinely worth trying this week.

You’ll also hear about:

(00:39) Introducing Francesca Hogi: love coach, TED speaker, and two-time Survivor contestant

(04:19) What Survivor taught her about connection that practicing law never did

(07:14) The Fourth of July barbecue that accidentally led her to matchmaking school

(12:03) What she learned matchmaking that most people never expect

(15:02) Why she shifted from matchmaking to coaching: “teaching people to be their own matchmaker”

(16:42) What led her to make flirting the topic of her TED talk

(18:09) Francesca’s actual definition of flirting, and why it’s not about being sexy

(19:42) Can you flirt by text? Her answer, and what “playful energy” actually looks like

(23:11) The “puke test”: how to tell when there’s genuinely no chemistry

(24:43) Why flirting can create chemistry that wasn’t there to begin with

(26:34) Connecting this to Alyssa’s four-date-minimum approach

(28:13) Why Francesca tells clients “rejection isn’t real”

(30:40) What to say to someone who thinks flirting feels performative

(34:38) The “fairy tale industrial complex” and why we don’t get taught how to date

(43:43) What Francesca’s “dating needs to be rebuilt” Instagram post actually meant

(46:00) Why dating needs subcultures instead of one-size-fits-all apps

(50:37) The “meet cute mindset” challenge, and how it changed Francesca’s own dating life

(52:41) Phones down, eyes up: the simplest shift with the biggest payoff

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Learn More About Francesca Hogi:

Visit her website: https://www.francescahogi.com/

Order her book, How to Find True Love: Unlock Your Romantic Flow and Create Lasting Relationships: https://www.francescahogi.com/book

Follow Francesca on Instagram: https://www.instagram.com/dearfranny/

Learn More About Alyssa Dineen:

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Alyssa sits down with Katherine Paulsen, a longtime coach on the Style My Profile team, for a wide-ranging conversation between two dating coaches at very different life stages. Katherine, 34, and Alyssa, 53, compare notes on what dating actually looks like in your 30s versus midlife, starting with the biological clock pressure that can push younger daters into relationships that aren't right for them, and the reframe midlife daters get to use instead: the luxury of time, and the luxury of already knowing yourself.

From there, the conversation moves into practical territory. Katherine shares the story of the singles PowerPoint she made the night before her wedding (yes, it led to a real relationship), and the two talk through other low-pressure ways to meet people in real life, from book readings to the Skint email list to simply committing to one new event a month and staying off your phone while you're there. They close out with an honest read on the current state of the apps: why Hinge's free version is getting harder to use, why Tinder might be having a comeback, and why there's still no single "magic app," just trial, error, and staying open to trying something new.

You'll also hear about:

(00:41) A quick note on Alyssa's free Date Vanilla webinar

(03:24) Dating in your 30s vs. dating in midlife: comparing the pressures

(04:22) How the biological clock pushes younger daters into settling

(05:32) Reframing time as a luxury you have in midlife

(06:02) The client who met her husband at 83

(06:55) The advantage of already knowing yourself

(08:22) Why dating with less pressure to find "the one" often works better

(10:33) A story about meeting someone the night you least expect it

(11:49) Letting go of "is this my future spouse" on every single date

(12:43) Katherine's wedding singles PowerPoint, and how it actually led to a relationship

(17:02) Applying the same idea to reunions, dinner parties, and friend groups

(19:05) A callback to the dating potluck episode with Jill Foos

(19:43) Why it's important to balance dating apps with real-life ways to meet people

(21:18) Committing to one event regularly, and how that led to a real relationship for a past guest

(22:04) Simple body language shifts that make you more approachable at events

(23:45) Book readings, author events, and New York's "the Skint" email list

(25:37) Using ChatGPT to find events suited to your interests (and where single men might be)

(27:22) Why Hinge's free version is getting harder to use, and what that means for you

(29:18) Why the most-liked profiles aren't necessarily who you want to match with

(30:21) Tinder's possible comeback, and why its immediacy has upside

(32:50) How Feeld has shifted from hookup culture to intentional dating too

(35:10) The bottom line: no magic app, just trial, error, and staying open

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Mentioned in this episode:

The Skint (NYC free events email list): theskint.com

Learn More About Alyssa Dineen:

Visit Style My Profile: https://stylemyprofilenyc.com/

Follow Alyssa on Instagram: /alyssadineen

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Episode Summary

In this solo episode, Alyssa tackles two patterns showing up again and again in her coaching calls. First: what happens when you have "more" than the man you're dating: more income, more savings, more financial stability, and how that fact can turn into discomfort, guilt, or a reason to walk away from someone who might actually be good for you. Alyssa breaks down why this isn't a money problem, it's a conditioning problem, tracing it back to inherited cultural scripts about men as providers, and shares two real client comparisons that show how little a job title actually tells you about someone's financial reality or character.

Then she shifts to something connected: why so many of you following the Burned Haystack method feel like you're barely dating at all right now, and why that's often a sign the filtering is working exactly as intended. She revisits her Date Vanilla framework (with her own story about Yoav's decidedly unflashy profile) to make the case that a boring profile and a boring person are not the same thing, and that chemistry showing up late doesn't mean it isn't real. The throughline: stop filtering for what you were told to want, and start paying attention to how someone actually responds to who you are and what you've built.

You'll also hear about:

(01:37) What keeps showing up across Alyssa's coaching calls right now

(02:22) Why financial imbalance is a conditioning problem, not a compatibility problem

(03:12) The old belief that a man should out-earn or keep pace, and where it comes from

(04:19) The economic reality behind why some men look "less put together" financially

(05:47) A client story: two very different job titles, two very different financial realities

(07:09) Another client story: discomfort that had nothing to do with the relationship itself

(08:35) What to actually watch for in how a partner responds to your success

(09:24) The question to ask yourself before writing someone off

(10:17) Why the Burned Haystack method can feel like "barely dating," and why that's discernment, not failure

(11:39) Revisiting the Date Vanilla framework and why boring profiles don't mean boring people

(12:05) Alyssa's own story: Yoav's resume-like profile and no fireworks until date three

(13:29) Why most real success stories don't have chemistry right away

(14:15) Tying it together: the "I wouldn't have swiped right on him" pattern

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Alyssa Dineen sits down with Sarah Gormley, author of The Order of Things, a memoir about grief, reinvention, and falling in love in her forties at the exact moment she least expected it. After 25 years climbing the corporate marketing ladder in New York and San Francisco, Sarah moved back to her childhood home in Ohio to care for her dying mother, and unexpectedly fell in love with Camillus, someone she'd known peripherally since childhood.

Sarah and Alyssa dig into what actually made that relationship possible: five years of therapy before she ever met him, and a slow unlearning of the belief that she had to earn love by being impressive. Sarah introduces her therapist's concept of the "Velcro effect," the idea that when you feel bad about yourself, you attract and stay attracted to people who confirm that feeling. They talk candidly about the pull to second-guess a good, steady relationship simply because it doesn't check the boxes society trained us to look for, and how much of lasting connection actually comes down to small, unglamorous things: what's for dinner, who texts back, whether someone shows up the way they say they will. This episode is a real, unfiltered look at what readiness for love actually looks like, and why it rarely arrives on schedule.

You'll also hear about:

(01:21) Sarah's move from San Francisco back to her childhood home in Ohio to care for her mother

(02:06) Meeting Camillus during the hardest, least "ready" season of her life

(04:26) Five years of therapy before meeting him, and what "readiness" actually meant

(05:33) Sarah's history with self-loathing and the pressure to be "smart, skinny, and successful"

(08:08) Letting go of "put-together Sarah" and learning to feel worthy for existing, not achieving

(11:39) Her mother witnessing the relationship before she passed away

(14:21) What it felt like to date without games, anxiety, or decoding text messages

(17:06) The temptation to sabotage a good relationship out of fear and old patterns

(19:56) Whether the relationship could have worked at an earlier, less ready point in her life

(21:44) Second-guessing a partner who doesn't fit the "type" you thought you needed

(26:36) The "Velcro Effect": why feeling bad about yourself attracts the wrong partners

(28:49) Prioritizing kindness and consistency over the qualities she thought she wanted

(30:16) Returning to her childhood home and rediscovering an earlier version of herself

(34:43) Real life after the fairy tale: living together, house hunting, and the everyday work of a relationship

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If this episode resonated, please rate, review, and share, it helps more people find the show.

Learn More About Sarah Gormley:

Visit her website: https://www.sarahgormley.com/

Order The Order of Things: https://www.sarahgormley.com/purchase

Follow Sarah on Instagram: https://www.instagram.com/scgormley/

Learn More About Alyssa Dineen:

Visit Style My Profile: https://stylemyprofilenyc.com/

Follow Alyssa on Instagram: /alyssadineen

Follow Alyssa on TikTok: /alyssadineen

This week on The Dating Lab Alyssa Dineen sits down with National Board Certified health and wellness coach Jill Foos for a candid conversation about post-divorce dating, unexpected matchmaking, and navigating the complexities of menopause.

Jill shares her unique story of how she met her partner, Noah, after being set up by a group of divorced girlfriends sharing their dating experiences. She opens up about the mistakes of dating too early during separation, why she decided to hire a therapist as her dating sounding board, and the importance of ditching superficial requirements, like the notorious "six-foot-tall" rule, to find genuine connection built on humor, kindness, and character.

Alyssa and Jill also explore the significant impact of perimenopause and menopause on a woman’s confidence, physical appearance, and libido. They discuss the realities of hormonal changes, the concept of responsive desire, and why it is crucial for midlife women to rebuild their healthcare team and their sexual pleasure toolkit.

This episode is an empowering reminder to stay open-minded in dating, advocate for your personal health, and embrace the reinvention that comes with midlife.

You’ll also hear about:

• (03:25) The "dating potluck" setup: How Jill met her partner Noah through friends
• (06:55) Why dating during a separation is chaotic and often a mistake
• (09:29) Using a therapist as a sounding board while navigating the dating world
• (10:28) Breaking old dating strategies and moving past instant "sparks"
• (15:00) Why height requirements restrict your dating pool
• (18:40) Finding attraction through humor, kindness, and active listening
• (22:15) Waiting to be intimate and discovering great sexual chemistry
• (26:00) Manifesting a partner who checks the most important boxes
• (30:14) The physical and emotional toll of perimenopause on dating confidence
• (34:00) Rebuilding your midlife healthcare "board of directors"
• (38:28) Managing low libido with HRT and testosterone
• (40:40) Rebuilding your sexual pleasure toolkit and understanding responsive desire
• (44:25) Why advocating for yourself in the doctor's office is essential

Listen on Apple Podcasts, Spotify, or wherever you get your podcasts.

If this episode resonated, please rate, review, and share - it helps more people discover the show.

• Follow Jill on Instagram
• Connect with Jill on LinkedIn
• Visit her Website

• Visit Style My Profile
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• Follow Alyssa on TikTok

Alyssa Dineen sits down with resilience and relationship coach Susannah Ludwig for an insightful and uplifting conversation about navigating the emotional aftermath of divorce, rebuilding confidence, and finding joy in midlife dating.

Best known for transitioning from an Academy Award-nominated film producer to a full-time coach, Susannah shares how her own path through divorce led her to help other women reclaim their power. She opens up about the importance of community support, taking time to rediscover what lights you up, and why true resilience is about finding strength right in the middle of the pain.

Alyssa and Susannah explore the intersection of vulnerability, self-worth, and dating after a major life transition. They discuss practical ways to trust your own judgment again, how to tap into your nervous system on dates, the realities of long-distance relationships and blended families, and why dating as a divorced parent can actually be an incredibly freeing and fun experience.

This episode is an empowering reminder that divorce is not just an ending, but an opportunity to design a life you truly love and to re-enter the dating world with clarity and purpose.

• (02:47) Transitioning from an Academy Award-nominated film producer to a full-time coach
• (05:39) The power of community and Susanna's monthly divorce support group
• (07:44) Finding yourself in the "in-between" stage and rediscovering forgotten passions
• (10:43) What women say they need after divorce vs. what they actually need
• (13:16) Susanna's dating journey: going on 60 dates and viewing it as a human study
• (22:06) Why vulnerability is the necessary key to relationship development
• (24:58) How to rebuild confidence and trust your own judgment again
• (27:30) Healing and regaining self-worth after a partner's infidelity
• (30:19) The common patterns of healing: from grief and anger to ultimate freedom
• (31:11) The distinct differences between therapy and coaching
• (33:03) Why dating as a divorced parent can actually be fun and liberating

Listen on Apple Podcasts, Spotify, or wherever you get your podcasts.

If this episode resonated, please rate, review, and share - it helps more people discover the show.

• Follow Susannah on Instagram
• Visit her Website

• Visit Style My Profile
• Follow Alyssa on Instagram
• Follow Alyssa on TikTok

In this refreshing and lively episode, Alyssa Dineen sits down with Kym Canter, a luxury sustainability pioneer specializing in bio-based fur and ethical lab-grown diamonds, for a candid conversation about transforming your mindset around online dating. Having bonded at a fashion industry event over their mutual, unlikely love for the digital dating landscape, Alyssa and Kym dissect why so many midlife adults encounter a wall of "cringe" and fear, and how to entirely rewrite that script.

Kym shares her journey as an early online dating pioneer, explaining how her natural entrepreneurial drive helped her view matching platforms not as something demeaning, but as a brilliant technical ecosystem akin to online shopping or adopting the first cell phones. Together, they challenge the traditional pitfalls of conventional setups, such as the inherent awkwardness of fracturing friend groups or dealing with vicarious matchmakers, and highlight the liberating freedom of stepping into a massive, independent market of new people.

From hilarious tales of accidentally dating the exact same man twice due to a profile picture swap, to navigating severe outliers like a deceptive married match that prompted a Marie Claire feature article, Kym and Alyssa provide a masterclass in treating dating as free self-analysis. This episode serves as an empowering reminder that finding a partner in midlife is less about avoiding failures and more about embracing them as valuable data, letting go of outdated collegiate scripts, and step-by-step rebuilding your social confidence.

• (00:45) Meeting Kym Canter: A sustainability pioneer bridging the luxury fashion world and online dating.
• (06:05) Shifting midlife mindsets: Dropping old college dating scripts for a changing modern ecosystem.
• (12:15) Desktop monitors to mobile apps: The business genius behind the evolutionary shift to swiping.
• (18:05) The "Den Mother" approach: Pushing younger generations to invest in premium, high-value profile filters.
• (24:20) Sharing app biases: Alyssa and Kym break down their long-term partner success stories on Tinder.
• (30:15) The forced chemistry trap: Learning to stop over-analyzing text messages and forcing interest.
• (36:10) Clarifying text intentions: A humorous lesson on misreading a late-night invite and setting clear standards.
• (42:15) Customizing modern commitment: Rejecting traditional relationship timelines for what actually works.
• (48:10) The entrepreneurial parallel: Re-framing bad dates as dud business meetings on the journey to a successful win.
• (54:20) Sustainable designs: Kym's solar-powered lab-grown diamond venture and how to connect with her brand.

Listen on Apple Podcasts, Spotify, or wherever you get your podcasts.

If this episode resonated, please rate, review, and share—it helps more people discover the show.

• Follow Kim on Instagram
• Visit The Invisible Jewels

• Visit Style My Profile
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• Follow Alyssa on TikTok