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Exposing Our Biggest Dating Mistakes Part 1


Kait and JJ Tomlin

Today Kait and JJ are telling more of Kait’s story though her biggest mistakes in dating from stalking, to a ferrari date. 


Hey Heart of Dating family!!! We’re back with another episode in our tools to thrive in singleness season. Today’s episode is JUICY and the first of two episodes (watch out for Friday’s episode for part 2). Today’s episode is exposing our biggest dating mistakes part 1 and we’re mainly focusing on Kait’s story. Kait is getting really vulnerable and sharing more specific stories she’s never shared publicly. The heart of today is for you to learn and grow from Kait’s mistakes. Let’s dive in!!

Controlling Guys

Earlier in her life, Kait never really noticed it when she was younger. However she does see it looking back. Control was the only way she could make sense of the chaos. For Kait she wanted to feel like the guy wasnn’t going anywhere. This gets into her anxious attachment style. She also used control to get guys to do what she wanted them to do when she was younger. 

Kait tells the story of her high school boyfriend she dated for 5 years. He was a great guy but in high school he wasn’t sure if he wanted to go to college but Kait wanted him to. So she kind of forced him to apply and would threaten things like, not respecting him or breaking up with him if he didn’t go. She looks back now and sees how that wasn’t right. 

She tells another story from a guy she dated in her early twenties that she knew they weren’t evenly yoked or spiritually on the same page but she saw the potential in him. Sooo she kept nagging him to get a mentor and that pushed him away. 

Ultimately through these experiences she lost respect for the guys she was dating. 

How did you disguise the control? She would disguise it with well these are all good things. She knew what she wanted in a guy and wanted to make them into that guy. This really stemmed from her caring what people thought about HER. 

What would you say to the girl listening, who says, yeah that’s kinda me? 

There are three core needs of a man. 1. Autonomy 2. Remain themselves 3. Needed and appreciated. She sees now that she completely depleted some of those through trying to change them. Trying to change someone really just hurts both of you. 

Became Guys’ Therapists

This happened more when she started healing and doing more work on herself. This was actually more recent even in Heart of Dating years. It would be like read this book, take this test, etc. It’s one thing if they brought it up and had questions or expressed interest but telling them they needed to do all these things was acting as a therapist. Kait was dating a LOT of potential at the time and was going to help them become that through the coaching and support she was giving. 

Do you feel like you gained a lot of significance and value through that? 

Absolutely! It goes back to she also didn’t respect them. 

Crossing Boundaries

Kait made a lot of mistakes. Here are some things she did, even after she stoped having sex and was actively working on her godly sexual ethic…making out early on, dry humping, spooning, thrist trap photos, flirty texting, sexting but not a ton, and sleepovers sometimes. 

Her sexual ethic had to be really deeply rooted to overcome this. Her why wasnn’t super deep yet and worked out that conviction with the Lord. She also didn’t set herself up at times with great accountability. She also struggled with masturbation in her early twenties and it wasn’t until she opened up and confessed to a girlfriend that they kept her really accountable. She knew she wasn’t doing well on her own but wanted to do better so got really good accountability. 

What would you tell yourself or someone who just decided to recommit to their sexual purity? 

Kait would say what her therapist told her, which was that you have to quit cold turkey. Be really brutal with yourself. Don’t watch things with sexual things, don’t kiss a guy. You’re going to have to go really extreme with yourself if you really want to see a change. Holiness has to be real and honest. 

Overtexting- ESPECIALLY to Affirm/ Thank Them

Kait was an overtexter especially to affirm them or thank them extensively. When she checked in with her intention she wanted to thank them but she also wanted them to think that she just really valued them and thought they were amazing which was a PERFORMANCE. She would take the reigns early on to plan really romantic things for them to make her stand out. She wanted them to think there was no other girl like her so they wouldn’t leave her and would remain close. 

Which also leads into… 

Being in Performance Mode/ Auditioning to be a WIFE

Kait tells a story about a guy she dated and was like 2 or 3 months in. She knew his favorite car was a ferrari so she rented it for a day for him and had a whole itinerary for the whole day which wasn’t cheap ($600)!!!! She wanted to be the best. It was more for her then for him. What’s the motivation behind doing this thing? 


Instagram stalking mainly! There’s a level of this being okay BUT she felt like she was doing it too much. If she felt off with her anxious attachment and would investigate and get wayyy too in the weeds. If you sense something in your gut and confront them, and they’re defensive…the worst thing you can do is try to control and force them. You need to pay attention to how it makes you feel and decide if you want to walk away or not. The desire to be liked and have connection was deep. She knew that she was worth more but there was a balance and a fight happening. 

What would you tell yourself or someone else if they just found out he was emotionally cheating? 

Ask a lot of questions and evaluate how you feel in the beginning. 

Comparing People to Ex’s

This was one main ex for Kait personally. She believed the lie that after that relationship no other guy could be romantic or woo her heart the way he had. Because she believed that lie nothing they did could level up. 

Don’t compare your relationship to other relationships. If you have good counsel and all of that is going well then don’t be comparing your relationship to everyone’s highlights. 

Were you extending grace and mercy to yourself while you were making these mistakes or were you only able to do that looking back or do you still carry bits and pieces of shame? 

It varies topic to topic for Kait. There are areas she has experience more healing and forgiveness than others. It’s not being perfect that matters, it’s being perfectable. - Ben Stewart 

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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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