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How I Knew...

with

Kait and JJ

Today we’re kicking off Season 19 of Heart of Dating with JJ and Kate sharing never-before-answered questions about their meet-cute, cringey first impressions, and what it really took for them to say yes to each other!

Introduction

GUYS! We’re back and kicking off a brand new season of the Heart of Dating Podcast!! Season 19, baby! This one’s called “How I Knew”. Get READY because we’re bringing you the stories and honest moments behind real couples’ journeys: the good, the wild, the hard. But before we spill all the tea from this season, we’re starting with something new! JJ and Kait are finally sharing the nitty-gritty of their own story. Questions they’ve never answered on the podcast before. Y’all, this is about to be so much fun. Let’s go!

How Did JJ and Kait Meet Anyway?

  • A Pandemic Meet Cute: JJ and Kait first crossed paths on a Zoom call for a Galentine’s conference in the middle of COVID. Kait was a keynote speaker, and JJ was there for a blind date segment. (00:40)
  • Did They Remember Each Other? Not exactly. Turns out Kait didn’t even remember JJ from the call. Which, to be fair, there were only about six people in that pre-call. Woops. (01:12)
  • Instagram Stalking: When JJ asked Kait out through the organizers, Kait had to stalk his Instagram to figure out who he was. Her immediate reaction: “Interesting in an interesting way”, especially because of all his wild hairstyles, including a mountain man beard, platinum, and blue phases. Kait says the clean-shaven look had “potential.” (02:31)

Almost Didn’t Happen

  • How Close Was It to a No? It was a super thin margin: Kait said the odds were like “51% yes, 49% no” as to whether she’d even do a FaceTime date with JJ. She figured he lived out of town, so, why not? (03:59)
  • When Did Interest Spark? Kait doesn’t remember every FaceTime detail, but JJ’s smile and sense of humor stood out. Fun fact: Even one of their friend’s kids later confirmed JJ is indeed a “funny guy.” (05:08)

First In-Person Meeting

  • Fate Steps In: Through a wild twist, when JJ came to LA, he ended up staying just a 10-minute walk from Kait’s apartment at a friend’s house. Their first meeting in person was a simple walk to meet in the middle. JJ showed up strutting, and brought flowers. (06:06)
  • First Date Fashion: JJ went with camo pants, a black tee, a denim shirt, platinum hair, and Air Force Ones with a smiley face. The verdict? “It was a lot.” Fashion critiques came fast. (08:34)
  • Early Cringes: It gets better! The most cringe thing JJ did? His texts. Think: LOTS of emojis and a lip-biting selfie. Both admit that going back to those early messages is, well, rough. (10:03)

Red Flags, Second Thoughts & Real Talk

  • Did Either of Them Almost Bail? Oh yes. Right after that first visit, Kait almost called it quits. She couldn’t get past JJ’s style and emoji enthusiasm. Also, his nickname in Switzerland (“Gigi”...which he swears he didn’t invent) had her questioning if he was even straight (after her past experiences). No, seriously: she even texted JJ to ask while boarding a plane and then put her phone in airplane mode so she wouldn’t have to see his reaction right away! (12:00)
  • Lowering Standards? Kait admits she had to adjust a little, especially about style, and JJ’s lack of therapy background. Generational gaps came up too, being six years apart. (14:38)
  • Did They Have Exit Strategies? Not really! After a month of FaceTiming, Kait figured she could always hang up if she had to. JJ may or may not have had a strategically-timed phone battery death… (16:00)
  • “Fixer-Upper” Moments: Kait jokes that style and eating manners were on the list to “fix,” but in her words, “you still have your own flair, that’s for sure.” Manners? Still a work in progress! (17:01)

Hard Moments: Burnout, Depression, and Commitment

  • In Too Deep to Walk Away? JJ teaches to always keep a “good grip on your walkaway power.” But during months 4–6, Kait went through major burnout and depression, and things got rough. JJ admits he almost left. Not for lack of love, but because sometimes, you just need to be single to heal and work on yourself, not in a relationship. They both prayed and sought counsel. Kait committed to real change, and the relationship improved. 19:02
  • Wisdom for Tough Seasons: The take-home: don’t rush to break up just because it’s hard. Pray, seek wisdom, invite counsel, and don’t operate out of scarcity or fear. (20:38)

Unique Decision: Not Saying “I Love You” Until Engagement

  • Why the Wait? JJ had never said “I love you” to a woman before and wanted those words to be backed up by action. For them, love is forged, not found. They chose to wait until engagement so “I love you” was a real promise. This was a reaction to both of their histories where “I love you” had been used lightly and often broken. (21:13)
  • It’s More Than Just Words: For Kait, who’d heard “I love you” from men who didn’t follow through, this meant everything. Now, it’s a pillar of their story and something they hope encourages others. (23:15)

Sneak Peek: Season 19 Guests & What’s Coming!

  • All the Stories: This season is stacked! Get ready for couples who met from “prophetic words” to those “still sleeping together as baby Christians,” to stories with breaks, redemptions, and everything in between. (24:05)
  • Featured Guests: Carlos and Alexa Penavega, Nika and Emeka, Tori and Chad Masters, D’Angelo and Whitney Moss, Mia Fields and Joran, Nicoletta Bradley (who had her own “The Holiday” meet cute in England), and Maddie and Grant Troutt. (24:41)
  • What to Expect: Wild variety, lots of wisdom, honest struggles and hope, plus some surprises! The goal? To encourage you, teach you, and remind you how unpredictable (and beautiful) God’s storylines can be.

Final Thoughts

We’re PUMPED for you to dive in! If you haven’t reviewed or ranked us on Apple or Spotify yet, it would truly mean the world! Help us keep these conversations and stories going! New episodes drop every Wednesday, so buckle up and let’s make Season 19 the best yet!!

Heart of Dating fam, let’s goooo!

Headshot of Kait

Kait Tomlin

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Kait Tomlin is a best-selling author, speaker, popular relationship coach, and the founder of Heart of Dating. She helps thousands of men and women on their journeys through the conversations on the Heart of Dating Podcast, which launched in 2018.

Through her ministry, Kait’s mission is to empower both men and women to have the courage to own their story, walk in victory, thrive with purpose, and discover clarity and vision in their life and relationships. In her new book, Thank You for Rejecting Me: Transform Pain into Purpose and Learn to Fight for Yourself, Kait vulnerably shares how she grew through her deepest, darkest rejections and offers readers the tools to heal from the past, take back their power, and walk in strength, victory, and love into their future. Kait currently lives in the Los Angeles area with her husband JJ and their pups Lovey and Teddy. She loves sunshine, walks, Jesus, and lip syncing to Celine Dion.

JJ Tomlin

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JJ Tomlin is a missionary kid born in Belgium, originally from Tennessee, and currently residing in the OC. He currently works in Gaming/E-Commerce, enjoys watching his Tennessee Titans on Sundays with his Goldendoodle Teddy and loves working with Christian men to raise the bar in singleness and dating.


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