
← Pleasure Project: Sex and Relationships6. Aug. · 46 Min.
Dating After 50 w/ Alyssa Dineen | Szn. 5 Ep. 6
<p>Dating in midlife can feel like a completely different world—<strong>especially if the last time you were single, dating apps didn’t even exist.</strong></p><p>Dr. Jenn Kennedy sits down with Alyssa Dineen, founder of Style My Profile, to talk about <strong>how to navigate modern dating</strong> with more confidence, authenticity, and a lot less burnout.</p><p>They unpack the <strong>dating profile mistakes</strong> that may be working against you, <strong>why old or overly curated photos can sabotage connection</strong>, and why <strong>chemistry doesn’t always happen on the first date. </strong>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.</p><p>They also explore <strong>dating after divorce</strong>, 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 <strong>“How did I feel with them?”</strong></p><p><strong>In this episode:</strong><br>• The biggest dating app mistakes people make in midlife<br>• What makes a strong—and authentic—dating profile<br>• Why messaging chemistry can create a false sense of connection<br>• Why attraction may take several dates to develop<br>• Dating from self-worth instead of seeking validation<br>• What actually makes someone attractive in midlife<br>• How to recognize dating app burnout<br>• When vulnerability becomes oversharing<br>• Why consistency and open-mindedness matter when dating online</p><p>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.</p><p><br></p><p><strong>Reach Alyssa At:</strong></p><p>Instagram: @stylemyprofilenyc</p><p>Website: <a href="stylemyprofilenyc.com" target="_blank" rel="ugc noopener noreferrer">stylemyprofilenyc.com</a></p><p><br></p><p><strong>Connect with Dr. Jenn:</strong></p><p>Instagram: <a href="https://www.instagram.com/drjennkennedy/" target="_blank" rel="ugc noopener noreferrer">@drjennkennedy</a></p><p>Website:<a href="https://pleasureproject.us/" target="_blank" rel="ugc noopener noreferrer"> Pleasure Project</a></p><p>Website: <a href="https://rivieratherapy.com/" target="_blank" rel="ugc noopener noreferrer">Riviera Therapy</a></p>