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Doing Relationships Right

Oct 4, 2022


Today, we've got the incredible Michael Kaye -- Head of Global Communications at OkCupid. He's got the inside scoop on being the best online dater you can be. He is also teaching Communications at NYU and is on the Board of Governors for the Human Rights Campaign.

Like me, Michael has made a career by helping people find success in relationships; it's our jam. We dive into the secrets to the best profile, cuffing season, the hookup culture change, and so much more!

"Ask your friends for help with your dating profile. Those people know you best." ~Michael Kaye

Today's conversation highlights the DOs and DON'Ts of online dating and how to spark that first online conversation and take it offline just in time for the cuffing season. (Listen to find out the deets of when it begins!) Michael shares all his inside advice to make the most of your time dating online.


As a bonus, Michael is offering to upgrade listeners to OKCupid PREMIUM for FREE!

You have to download the free app, set up your profile completely, and then email to let them know you heard the deal on Doing Relationships Right, and you'll get VIP access!

Thank you, Michael, for joining me and sharing your insider secrets from the excellent data from OkCupid! My listeners are LUCKY; you might have to rewind this one a couple of times, y'all! 

Peace, love, and truth,

xo j


Check out Michael Kaye on Instagram here

Here's the link to my Online Dating Course: DOING DATING RIGHT!   

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You can connect with my editor, Cianna Reider, at

Get a copy of Jen's book, "Woulda, Coulda, Shoulda: A Divorce Coach's Guide to Staying Married" here.

Show Notes:

[01:38] Introducing Michael Kaye

[03:10] Why Michael was drawn to OKCupid

[04:00] Why do people hate online dating?

[04:25] Why Jen always recommends OKCupid

[05:00] Why OkCupid brings in higher quality daters.

[05:38] Michael's tips on improving your profile.

[06:30] Stop being negative in your profile.

[07:26] Create your profile with questions people can respond to.

[10:08] Why you should lose the selfies on your profile.

[11:48] OKCupid's NEW photo messaging ability.

[12:34] OkCupid is rolling out selfie verification on the app!

[14:15] How to bring the conversation off the app.

[18:00] Update your dating profile more often!

[19:47] What is cuffing season?

[22:20] How to get a FREE premium subscription!!

[24:00] How to keep your cuffing partner long-term.

[25:26] The change in Hookup culture for GenZ.