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Mini Man-sode 49: Exposing Our Biggest Dating Mistakes Part 2


Kait and JJ Tomlin

Today JJ is bringing on Kait to interview him while he tells more of his dating story and his biggest mistakes in dating, from dating in a silo, to being a hypocrite. 


Hey hey MEN of Heart of Dating family (and ladies sneaking in)!!! We’re back with another mini man-sode and this week we’re actually building off of Wednesday’s episode! Today’s episode is JUICY and the second of two episodes (go back to Wednesday’s episode for part 1). Today’s episode is exposing our biggest dating mistakes part 2 and we’re mainly focusing on JJ’s story. JJ is getting really vulnerable and sharing more specific stories about his dating mistakes. The heart of today is for you to learn and grow from JJ’s mistakes. Let’s dive in!! 

SO you weren’t allowed to date until 17- what were some of the things you were taught about dating?

JJ wasn’t allowed to date until 17 and then they didn’t talk about it. He was so unprepared to go out in the world of dating and even more wasn’t prepared for the RESPONSIBILITY of dating. 

You wouldn’t date but YOU WOULD kiss/ makeout with girls is that right?!?!

From the age of like 17-24 JJ would actually boast about the fact that he didn’t date. There was some self-righteousness and pride there. He really was genuinely focused on God. BUT, he remembers that not always flowing into his single life. 

JJ tells a story of his teenage years where there were 4 girls he really thought he had a shot at dating. He actually put all their profile pictures together and he remembers the validation and power and confidence he felt knowing that he could get any one of them. This was one of the biggest lies and foundations of dating that set him up for failure. The idea that he was THE MAN if he could land the girl everyone thought was beautiful instead of the pursing of her. 

Up until the age of 24 he probably kissed or madeout with like 3 or 4 girls. He was still really flirty and texting girls. He would be in friendationships often. He remembers the thrill and the fun of having that kind of relationship without the actual commitment. 

Something happened in his sexual ethic when he afforded himself a hallpass for kissing and making out because it’s what everyone does. It may have been the first time he madeout with someone he didn’t know and in that moment it changed to a lie of “it’s JUST _____.” 

He felt like as long as he didn’t have sex or anything he felt good about himself. 

So… what did accountability and intentionality look like for you in dating when you did decide to date?

When JJ says that he just woke up with this feeling like he was ready to date…he was SO NOT ready. He had no accountability or counsel or community that knew anything about that. JJ says he probably thought he was doing well and being a godly man at this point. 

He says that it was pride that made him think he could do it on his own and didn’t need accountability. 

For JJ it was a combination of colossal failure, he found himself in this missional dating relationship. He KNEW they weren’t equally yoked. He was so distraught after this because this was the first time he had crossed some boundaries he hadn’t previously, like oral sex and that broke him. 

Sometimes guys in the church have really high standards and think really highly of themselves but when it comes to dating they’re not being intentional…were you doing this?

JJ says he was absolutely hypocritical. Everything he said in church and at small group wasn’t aligning with what he was doing in his romantic life at all. He was ghosting girls and purposely dating girls outside the church so he didn’t have to have any accountability. He would find himself going on dating apps, matching with women that they had no mutual friends with, he’d makeout with them and then he’d just never talk to them again. 

He had great friends but he wouldn’t let them see his true self, and let them in. He was leading a bible study group during all of this time. It was a secret dating life he had. He is so passionate to talk about this because he wasn’t the only one and nobody was saying that this was wrong. 

If there’s one thing that JJ has to accept the most grace for and carries the most shame for it’s the fact that he called himself a Christian and an ambassador for Christ and some of these girls he went on dates with were not really Christians. He’s so embarrased that their only impression of a cChristian man was him. He can only pray that God brings another Christian man that was stronger than him and better than him to leave them a lot better than he found them. 

There was just so much responsibility in dating that was too heavy for his character. When you find yourself in situations in life where the responsibility at hand is greater than the character you’ve clutiviated in Christ you’re going to massively fail and you’re not just going to hurt yourself you’re going to hurt everyone around you. 

Any last outstanding things you’d like to share?

By saying “I don’t date” he left himself open to so much unpreparedness. If you’re really going to do closed dating and be single then be a monk. Be 100% single if you’re in closed singleness and don’t leave the door cracked AT ALL. 

Second thing would be when you do find yourself in a place where you want to be in open singleness, have those boundaries, convictions, why you’re going to date, be SO clear, cemented in stone. 

Especially as a man, if you want to go out and date, it’s a tremendous responsibility. If you’re not mature, and your character, how you treat and leave women better than you found them, I BEG you, PLEASE don’t date. 

When you do date, don’t do it alone. Don’t be prideful and arrogant thinking you can go alone and date and do it well because you can’t. Do it with friends, do it with mentors, people who are so much smarter and wiser than you. Work up the courage to invite them into your life. Be ruthless about seeking it out. You need it regardless of what your history is and where you’re at in your dating life. 

1 Peter 5:6-8!!! 

Send this to a friend and say let’s talk. 

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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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