Episode 309: Online Dating After Divorce with Alyssa Dineen

Alyssa Dineen, founder of Style My Profile, joins me to talk about the ins and outs of online dating after divorce. If you’re feeling overwhelmed by the dating apps, unsure how to craft a compelling profile, or just wondering if you're ready to date, Alyssa’s expertise will help you navigate it all.

Together, we tackle the realities of modern dating, from building a profile that actually sparks conversations to avoiding burnout in the endless swipe cycle. Alyssa also shares her own post-divorce dating journey, including how she found love after leaving an abusive marriage. She also shares the key strategies she uses with her clients to help them date with intention.

You’ll also hear:

• The biggest mistakes people make with their dating profiles (5:24)
• How dating can help you re-discover who you are after divorce (7:23)
• The ‘date uniform’ strategy that makes getting ready effortless (37:46)
• The first date, avoiding dating burnout, and enjoying the process (26:37)

Learn more about Alyssa Dineen: With over 25 years of experience as a fashion editor, stylist, and art director, Alyssa established herself as a seasoned leader in the New York fashion world. In the past decade, Alyssa has also emerged as a pioneering figure in the online dating space. Her innovative approach combines her expertise in styling with her insights into dating, guiding clients on everything from personal presentation to effective communication with potential partners.

As an acclaimed dating expert, Alyssa has been featured in The New York Times, Today Show, Goop, and Oprah Daily. She is also the author of The Art of Online Dating published by Harper Collins in 2021, which offers valuable strategies for success in online dating. You can find more information about Alyssa and Style My Profile’s services at stylemyprofilenyc.com.

Resources & Links:

Unbreakable – the Divorce Recovery Retreat, Sedona, AZ in April 2025

Submit your questions here for possible inclusion in future Q&A podcast episodes

Focused Strategy Sessions with Kate 

Phoenix Rising: A Divorce Empowerment Collective

Style My Profile website

Alyssa is also offering 20% off her Mindful Dating 101 course and DIY Profile Kit to DSG listeners! Use code DSG20 at checkout.

Alyssa on Instagram

Style My Profile on Instagram

Alyssa’s Facebook Group for: Empowered Women Moving Forward in the Modern Dating World

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DISCLAIMER: THE COMMENTARY AND OPINIONS AVAILABLE ON THIS PODCAST ARE FOR INFORMATIONAL AND ENTERTAINMENT PURPOSES ONLY AND NOT FOR THE PURPOSE OF PROVIDING LEGAL OR PSYCHOLOGICAL ADVICE. YOU SHOULD CONTACT AN ATTORNEY, COACH, OR THERAPIST IN YOUR STATE TO OBTAIN ADVICE WITH RESPECT TO ANY PARTICULAR ISSUE OR PROBLEM.

Episode Link:

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