Dating in midlife can feel like a completely different world—especially if the last time you were single, dating apps didn’t even exist.

Dr. Jenn Kennedy sits down with Alyssa Dineen, founder of Style My Profile, to talk about how to navigate modern dating with more confidence, authenticity, and a lot less burnout.

They unpack the dating profile mistakes that may be working against you, why old or overly curated photos can sabotage connection, and why chemistry doesn’t always happen on the first date. Alyssa also challenges some of the assumptions women over 50 hear about dating, including the idea that men their age are only interested in younger women.

They also explore dating after divorce, how to stop seeking validation from potential partners, when to take a break from the apps, and why the better question after a date may not be “Did they like me?” but “How did I feel with them?”

In this episode:
• The biggest dating app mistakes people make in midlife
• What makes a strong—and authentic—dating profile
• Why messaging chemistry can create a false sense of connection
• Why attraction may take several dates to develop
• Dating from self-worth instead of seeking validation
• What actually makes someone attractive in midlife
• How to recognize dating app burnout
• When vulnerability becomes oversharing
• Why consistency and open-mindedness matter when dating online

If dating has started to feel more like a second job than a path toward connection, this conversation offers a more grounded way to approach it.

Reach Alyssa At:

Instagram: @stylemyprofilenyc

Website: stylemyprofilenyc.com

Connect with Dr. Jenn:

Instagram: ⁠⁠⁠⁠⁠⁠@drjennkennedy⁠⁠⁠⁠⁠⁠

Website:⁠⁠⁠⁠⁠⁠ Pleasure Project⁠⁠⁠⁠⁠⁠

Website: ⁠⁠⁠⁠⁠⁠Riviera Therapy⁠

Resentment rarely begins with one dramatic betrayal. More often, it builds quietly through unmet needs, unspoken expectations, unresolved conflict, and the small disappointments we convince ourselves aren't worth mentioning.

In this solo episode, Dr. Jenn Kennedy explores why resentment is one of the biggest threats to emotional and physical intimacy. She explains how it develops over time, the subtle signs it's taking hold, and why avoiding difficult conversations often creates more distance than the conflict itself.

You'll learn:

• Why resentment is a "slow leak" in relationships
• The most common causes of resentment
• How to recognize the warning signs before they damage your connection
• Why keeping score erodes intimacy
• Practical strategies for communicating needs and repairing conflict earlier

Whether you're feeling disconnected from your partner or simply want to strengthen your relationship before resentment takes root, this episode offers practical tools to help you create more honesty, trust, and lasting connection.

If this episode resonates with you, be sure to follow Pleasure Project: Sex and Relationships, leave a review, and share it with someone who could benefit from the conversation.

Ever wondered what actually happens at play parties? In this spicy follow-up, Dr. Jenn welcomes back gerontologist & domme Dr. Nicole Marcione for a candid, myth-busting conversation about sex parties, consent culture, voyeurism vs. participation, what to wear (and what to bring home), and how curiosity, not pressure, guides the experience.

This is an unfiltered, educational deep dive into pleasure, boundaries, aging bodies, and why your yes can always become a no. Perfect if you’re intrigued, nervous, or just wildly curious.

✨ Best paired with: ⁠Untying Ourselves w/ Dr. Nicole Marcione | Szn 4 Ep 2⁠

Reach Dr. Nicole at:

⁠⁠https://www.integrativeaging.com/⁠⁠

⁠⁠https://www.integrativeaging.com/mini-workbook⁠⁠

⁠⁠https://www.integrativeaging.com/InfluenceDomme⁠⁠⁠⁠ ⁠⁠

⁠⁠https://www.instagram.com/drnicolemarcione/⁠

Connect with Dr. Jenn:

Instagram: ⁠⁠⁠⁠⁠@drjennkennedy⁠⁠⁠⁠⁠

Website:⁠⁠⁠⁠⁠ Pleasure Project⁠⁠⁠⁠⁠

Website: ⁠⁠⁠⁠⁠Riviera Therapy⁠