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Red Flag: Age Gap, Cheating, Liars, Politics… and More


Kait & JJ Tomlin

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Kait and JJ are going through a smorgasbord of red flags in today’s episode answering some of the top things you guys sent in. 


Hey hey hey podcast fammm! We’re back with another episode in our Red Flags season!!! Today we’re going through a whole list of red flags you guys wrote that you wanted to hear about. We’re going to be covering a LOT so this is a really good one to listen in on! For this episode Kait & JJ will be acting as your dating coaches. Typically they prefer to ask questions and allow you to come to your own conclusions, but for the sake of this episode they’re going to tell you if they think it’s a red flag or dealbreaker. Let's jump into the episode! 

Age Gaps

We don’t think age gaps are a red flag per se, we think you need more information! The two biggest questions for you to ask are… 

  1. Are you looking to build the same things in life? This is more about the stage of life. 
  2. Do you both have a similar outlook on GROWTH? 

Think about their age in terms of LIFE EXPERIENCE and their POSTURE to GROWTH rather than the actual number. A good thing to ask yourself as you get to know them is… 

How much WISDOM do they have and how much WISDOM are they after?

Stage of life is HUGE! What they’ve been through in life is huge too. There are some people who have lived a lot of life at a younger age. 

Some things that can be hard with age gaps: 

  • Sometimes when dating older there can be a lack of willingness to grow depending on how set they are in their ways. 
  • It can be hard with FAMILY accepting age differences. 
  • There can sometimes be a worry about what people will think. 
  • The person will not always get references to things you understand if generationally you are pretty spread apart via age. Cultural things will be more difficult. 

A deal breaker though is a much older person wanting to date a MUCH younger person. 

Cheated in the Past

This is definitely a red flag! Is it a dealbreaker? This depends. 

Kait thinks you should always ask the other person when you’re on the cusp of getting into a relationship. It’s not a red flag if they don’t offer up the information voluntarily. YOU should always ask though! The huge thing here is to get VERY CURIOUS! Ask these questions… 

What did you learn? 

Why? What was the root of it? 

What would make this a dealbreaker is if they answer very superficially, blame the other person for their cheating, can’t give an answer for the root of it, OR if it was recently. 

If we’re being honest, we all will be tempted in relationships. If you see that they have acted on that temptation then it’s important to evaluate even more. 

You shouldn’t eliminate them solely based on the fact that they have cheated in the past. You should ask a LOT of questions. Things in their answers may reveal that this is in fact a deal breaker but it also may not. 

This isn’t just physical cheating either, this is ALSO emotional cheating!

Different Physical Boundaries

This is a red flag and could potentially be a deal breaker. 

What needs to happen is having an HONEST dialog with them. Are they willing to change convictions to come to where yours are? BUT ALSO, asking why their convictions were what they were to begin with. That’s SUPER telling! 

The thing is that one person is going to change and if you have stricter boundaries then it’s going to be you who changes because they will push the boundary. So that will be a conflict that you’ll have to be aware of and disciplined in. 

It’s more of a red flag and honestly a deal breaker if they don’t have a strong sexual ethic. Someone’s sexual ethic doesn’t define their salvation. However, it does reflect how deeply they desire to please God and glorify Him in everything they do. 

What if they recently had sex? This is a HUGE red flag, and depending on how recently, a deal breaker. It’s not a judgment toward them because we have no authority to judge them, it’s that we would seriously question their spiritual maturity in the way they’re running their life. You have to get really curious here again. 


JJ would say this is a big red flag because he thinks this is showing major insecurity they haven’t dealt with. 

Kait would say to get super curious, it’s not a red flag per se, but you need more information. If they’re not aware of their jealousy or willing to work on it, then that is a deal breaker. If they have some jealous moments and are aware of it, and it’s coming from past pain (like cheating), have anxious attachment, or struggle with abandonment then it’s possible the other person is doing something unintentionally or intentionally to trigger that. 

What can you do to create an environment of safety? 

Check in with yourself. Are you doing anything to make them feel uncertain? 

When jealousy becomes a deal breaker is when it begins to be a form of control. They’re not giving you autonomy to choose who you follow, who you spend time with, etc. Jealousy can be  a part of manipulation and abuse.


This is definitely a red flag! 

However, we use this word WAYYYY too much these days. We love awareness, however everyone is NOT a narcissist. Narcissism is a spectrum. 

Kait, personally defines 3 types of narcissism. 

  1. People who on OCCASION are really selfish. This is almost every single human being. 
  2. People who have very CONSISTENT narcissistic tendencies and it’s very clear. This is still low on the spectrum. 
  3. People who are very severely narcissistic, who have been diagnosed. 

Judgmental Christians

This is a red flag! 

If you’re not leading with genuine curiosity then that’s when you’re in the wrong. Leading with an accusation has never gone well. 

We see this in so many different areas… 





We’ve lost the ability to hold things in tension. The spirit of judgment is going to be very TOUGH to build a relationship with. Judgment is truth without grace. 

Obsessed with Politics

For Kait, this is definitely a red flag! 

If they’re obsessed with politics and NOT working in politics, this is a red flag. If you’re working in politics, then this can be a bigger deal because it takes up so much more space in your life. 

We’re not shaming people who are passionate about something. However, when politics have become the top priority or where you find your identity then that is a red flag. As Christians we should be a Christian FIRST and foremost. 

This is a very sensitive topic and there needs to be a lot of trust built to be able to have a conversation about politics because of the world we live in. 


This is definitely a red flag! 

Typically people lie to stay in control or because they have shame. We have a lot of compassion for lairs, but you have to watch out because a lot of abusers are liars. However, there are normal people who lie because of people pleasing or shame. 

The caveat here is that there is a time and place for withholding because of where they fall in your circle boundaries (we teach extensively about this in School of Dating). 

You want someone who is going to be forthcoming and you don’t have to ask a ton of clarifying questions. 

How are you running your life in the little moments? 

Overall, we want you guys to get curious about people. Ask more questions and get to the root! With that being said, there do end up being deal breakers as you hear their responses and learn more. 

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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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