Should I Keep Dating Him? When To Call It Quits

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I was raised in the 90’s. Do you know what that means? That means that girls all around me were “kissing dating goodbye.”

The bestselling book I Kissed Dating Goodbye was a hit. Teenagers everywhere gave up dating and started a courtship system instead.

My mom shrugged and continued to teach me the way she already had been. She taught me that I was worthy and valuable. That I had dignity and purpose. She taught me that God’s apparently restrictive rules about intimacy between men and women were actually a gift to protect our relationships and our emotions.

And she taught me to date.

She taught me to go out with boys and learn what I liked and what I didn’t like about different personalities. She taught me to respect myself and expect the same from them. And above all else, to look for a man who would be a spiritual encouragement, a partner in my faith.

Dating still gets a bad rap in some circles, but here are some things I learned from dating:

• If a guy was good-looking, but that is the only thing he had to offer, the fun wore off pretty quickly.
• If a guy was very spiritual but didn’t make me laugh, that also got dull quickly.
• If a guy wasn’t interested in my family, or rolled his eyes at them, I wasn’t interested in him.
• Broken hearts hurt. But they also heal.

I’m so thankful for those lessons. (And I’m so thankful for my Steve. I’m so glad that I’m done dating!)

But if you’re still riding that dating train, I know one question you are probably asking:

Should I keep dating this guy or girl?

She slurps her spaghetti. He bites his fingernails. He’s not very masculine. She’s not into sports.

Or maybe he checks all those boxes perfectly but you just aren’t that into him. How do you know when to call it quits?

Good news! I created a flowchart! I love flowcharts because they solve all your problems like a math formula for life. (I’m kidding…but only partly.)

The Dating Formula

The Bible says that we should love God with our heart, soul, mind, and strength, which indicates our whole selves. We are made up of emotions (heart), spirit (soul), mind, and body (strength).

Our relationships with others, especially with our eventual spouses, should be relationships that demonstrate compatibility and mutual encouragement.

For the purpose of this article I define compatibility as the ability to enjoy another’s company, to agree on things that matter the most, and to have the freedom to be yourself. Mutual encouragement takes compatibility a step further, with the added element of lovingly helping each other learn to be the best versions of yourselves.

Mutual encouragement means that you are each better off for having been together.

Mutual encouragement means that you are better in your heart, soul, mind, and body because of this relationship.

1. Spiritual Compatibility & Mutual Encouragement

“And let us consider how to stir up one another to love and good works, …encouraging one another”
Hebrews 10:24-25 ESV

When Steve asked me to marry him, he asked, “Will you serve God with me for the rest of our lives?” (Swoon.) He had a picture in his mind of what our relationship would look like spiritually. We would serve God together. We would use our gifts together. Our relationship would orbit around God.

It was imperative that I be on the same page as Steve. That was his highest priority and greatest value. (Good news – I was right there with him. See? Compatible.)

You don’t need to be involved in full-time ministry together, of course, but you need to be on the same page spiritually. You both need to hold your relationship with God with the same grip. If you hold tightly to God and your boyfriend or husband barely cares, you will eventually find your own grip loosening to walk in step with your husband. Or you will be distanced from him as you walk with God.

It’s a difficulty in your relationship that you can avoid with careful evaluation.

Also, pay careful attention to the ways your physical relationship is building you up or tearing you down spiritually. Are you walking together with God or leading each other astray?

Finally, a quick note of encouragement: It’s common for new relationships to feel all-encompassing at first. You may be sitting in church and catch yourself thinking of the other person. Or maybe you’ll try to pray and start to think about them instead. Don’t panic! This is common early on in a relationship but it will pass.

2. Emotional Compatibility and Mutual Encouragement

“So flee youthful passions and pursue righteousness, faith, love, and peace, along with those who call on the Lord from a pure heart. Have nothing to do with foolish, ignorant controversies; you know that they breed quarrels.” 
2 Timothy 2:22-23 ESV

“Be kind to one another, tenderhearted, forgiving one another, as God in Christ forgave you.”
Ephesians 4:32

“A soft answer turns away wrath, but a harsh word stirs up anger.”
Proverbs 15:1

TV Shows love to portray the older couples that gripe at each other. We laugh at their banter and go on with our day. But can you imagine what it would be like to be in a relationship like that? Maybe you have been in a relationship like that. The harsh answers and quarreling become a habit and it can even begin to feel normal.

In your relationship are you mutually encouraging emotionally? Do you allow the other person to express their feelings and their emotional needs freely, and approach them with tenderness? Or do you have a relationship that’s based on ugly sarcasm or hurtful comments?

3. Mental Compatibility and Mutual Encouragement

“Iron sharpens iron, and one man sharpens another.”
Proverbs 27:17 ESV

Pride and Prejudice by Jane Austen portrays Mr. and Mrs. Bennet as a married couple who are unfortunately incompatible mentally and emotionally.

“Her father, captivated by youth and beauty, and that appearance of good humour which youth and beauty generally give, had married a woman whose weak understanding and illiberal mind had very early in their marriage put and end to all real affection for her.“
–Pride and Prejudice by Jane Austen

Of course, every married couple doesn’t need to have an IQ test to determine compatibility, but it’s reasonable to expect to be able to carry on a healthy conversation that is interesting to both parties.

The easiest way to fall into a trap of never realizing how mentally incompatible you are is by never talking. Spend every date watching movies or fill up those awkward moments with makeout sessions and one day you may find out you never had anything to talk about.

If you feel like you’re falling into that trap, try reading a good book together – or a bad one – and talk about it.

4. Physical Compatibility and Mutual Encouragement

Strengthen me with raisins, refresh me with apples, for I am faint with love.
Song of Solomon 2:5

What we’re talking about here is chemistry. There are happily married couples from ages past who would argue that physical attraction can grow from love, and I believe that’s true. But I also believe that physical attraction is an important element in a marriage.

Chemistry goes deeper than just perceived attractiveness. It’s what makes you draw near. It’s what makes you want to get closer to this person.

If we’re talking about the whole person: the heart, soul, mind, and body we can’t ignore the attraction to another person that comes from our body.

So let yourself ask (admit it, you already have): Does this person have a cute dimple? Beautiful eyes? Strong arms? Do I find this person attractive? Is there chemistry?

And A Little Room To Grow

Taken together as a whole, your impression of who this person is spiritually, emotionally, mentally, and physically, and who they are becoming, will give you an idea of whether you would like to continue this relationship or not. You may choose to end the relationship, to continue it, or to give it a little more time to decide.

The real question is who are they? And who are they becoming? And is that something you want to be a part of?

But remember that they aren’t finished yet. And neither are you! Spiritually, they will have slumps or discouraging days. But if they are a believer, then they will have the Holy Spirit to help them grow. Emotionally, they may be having a hard day, or dealing with a tough situation. Mentally and physically they may not be winning Jeopardy or climbing Everest. But the real question is who are they? And who are they becoming? And is that something you want to be a part of?