Dating After 50 w/ Alyssa Dineen | Szn. 5 Ep. 6

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