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HOD SELECT: How to Spot The Top Red Flags and Dating Dealbreakers


Meygan Caston

This week on the Heart of Dating podcast Kait talks to Meygan Caston from Marriage 365!

Meygan Caston is the co-founder of Marriage365, a nonprofit dedicated to helping couples connect on a deeper level. She and her husband Casey reach millions of couples around the world each month with their resources including books, retreats, online courses, webcasts and they just released a brand new membership site called MyMarriage365.
Meygan, her husband Casey, their two kids and dog Hobie live in Orange County, California. She loves the beach, dance parties, writing, spa days, and of course — Jesus! Her life-long dream is to walk the Camino, have lunch with Brené Brown (which the ladies talk about at length) and get on The Price is Right.

On this episode Meygan and Kait talk about some of the most popular and biggest red-flags to become aware of when it comes to dating. They also talk about how to become more self-aware, work on yourself in different seasons of dating, and why connecting with someone who has the same values in God is SO important. We are so excited for you to listen to this episode filled with so much wisdom!

Tell us more about you and Casey and what you both do?

  • We’ve been married 16 years and met in college. After marriage, Casey and Meygan realized there were some real #struggles.
  • They wanted to create resources for couples to be better equipped for relationship in dating and marriage.
  • Marriage 365 is their ministry consisting of retreats, books, resources, and even an app!

Why do we commonly miss red-flags?

  • When dating, we’re typically on our best behavior.
  • We also tend to look at the positives starting off, ignoring red-flags.
  • The culture of introducing sex early on in a relationship makes a poor foundation for a relationship which often leads to missing red-flags.
  • Sex before marriage and before getting to know one another, distorts good judgement.
  • “If you can practice self control before you’re married, you’ll be able to practice it after you’re married”
  • Hard times are actually good to go through when you’re dating!
  • Many people do recognize red-flags, but just minimize them hoping that marriage will fix them.

Can you name the top 5 red-flags?

  • Extreme mood swings: Constant mood swings are a red-flag for unresolved conflict or mental illness.
  • Lack of Integrity: If someone is choosing the easy way out, even in small things, it shows a lack of integrity and that’s a red flag.
  • Family of Origin Interactions: If they’re very negative about their family, disrespect them, treat them poorly, or gossip about them frequently, that is a big red-flag.
  • Interactions with the Opposite Sex: If they are flirtatious, have one-night stands, are still close with their ex… then this a red-flag. “If someone is very flirtatious to the opposite sex when they’re single, it means they may have the tendency to continue to be flirtatious in marriage.
  • Screen-Time: Pay attention to how much time they spend on their phone. Too much time being spent on a screen also increases the chances of them watching porn.

What is the difference between red-flags that can be worked on and red-flags that are total dealbreakers?

  • Most people just don’t know HOW to do relationships well, so you do have to give your partner an opportunity to shine.
  • Relationships are about communication and progress. Be curious and observant!
  • Remember, you’re both learning and growing!

Are there specific questions to ask to find out if certain red-flags exist?

  • You have to learn and talk about past relationships, “what did they teach you about love, trust, and commitment?”
  • You don’t really want to hear “I don’t know” as an answer for deeper questions as it shows that they haven’t really thought of things before. If this is the case, give them time to process what their thoughts may be.
  • Remember, “You teach people how to treat you”.
  • Talk about family of origin with them, their family foundational background is an important aspect to consider.
  • Look for teachability!

What are some TOP deal breakers?

  • Abuse and addiction. You cannot help an addict unless they help themselves.
  • If you see your boyfriend or girlfriend as an emotionally lazy person… then that a deep dealbreaker as you’ll be setting yourself up for a really hard marriage.
  • Selfishness does NOT belong in marriage.
  • If you don’t have the same faith values, it WILL cause problems in the relationship!
  • Unaddressed mental health issues.
  • Extreme introverts with extreme extroverts don’t typically work together.

How do you know something is an issue you need to be patient on or break up because of?

  • First of all, you have to ask if you’re willing to be with this person if it doesn’t change.
  • You can’t force someone to change, if there’s an issue it will magnify in marriage.
  • Communication is key!

Where’s the line between encouraging someone in faith vs. rescuing someone in faith?

  • If you try to rescue someone, it’s like the other person becomes a project.
  • The other person needs to want to pursue a relationship with God on their own.
  • Rate yourself on how much you value your relationship with God and find someone who has those same values and is at the same level of you.
  • Before you can judge their faith you have judge yourself first.
  • Look for the willingness to get closer to God.

If you don’t have peace with the other person, how do you navigate that?

  • Pay attention to those feelings and don’t minimize them.
  • If you’re not “feeling it” when you’re dating, you’re not going to feel it in marriage.
  • If you’re not having peace… don’t ignore it! Process through those feelings with a mentor.

If the person sees a lot of red-flags, how do you move forward with a healthy and kind break-up?

  • Pinpoint one or two things that may be the issue, write them down, and practice what you’re going to say when you break up. This gives you confident.
  • Be respectful!
  • Kiss, kick, kiss method (or sandwich method)!
  • Don’t go into the conversation with anger, bitterness, or unforgiveness!
  • Remember, the only thing you can control is yourself. You cannot control the other person.
  • Be Confident!

If you break-up and there’s still a desire to be together, how does one navigate that?

  • If an issue was fixed, then go ahead and get back together, but if the core issue was not fixed… it’s not going to end well.
  • Don’t get back together simply because you miss each other.
  • If you do break-up, Meygan recommends waiting at least 6 months before trying again and seeing if the issue in question was truly fixed.
  • Healthy people recognize ‘I can always be better than I was yesterday’”

What’s your final nugget of dating advice?

  • “If you want to make a better marriage, make a better YOU”
  • First we have to look at ourselves.
  • Get curious with yourself! If you have red-flags, then work on yourself!
  • Work on self-awareness and get yourself healthy!

Other Resources:

Follow them on Facebook HERE

Follow them on Instagram HERE

Visit their website HERE

Get the book 365 Connecting Questions HERE

Visit their Premarital Course HERE

*use 20% off code HEARTOFDATING20 for the online premarital course and the connecting questions books

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