When You Don’t Feel Good about Who Your Son is Dating

One thing I have learned about parenting is that kids grow up in stages.

Just when you think you have one stage figured out, circumstances change, and suddenly your child is thrown into a NEW stage that puts you back at square one.

In preschool and kindergarten, boys and girls become friends. They invite each other over to play and don’t really see their differences. But around first grade, the two genders part ways. Invisible lines get drawn, and the boys hang out with boys, and the girls hang out with girls. They fall off each other’s radar until typically the spring of fifth grade, when they notice each other again.

In middle school, the boy-girl interactions amp up. They get crushes and have awkward conversations. Since their relationships are short-lived, a parent’s concerns are short-lived too. Give it a week, and a break-up is forgotten.

But in high school, dating can take on a life of its own. Hormones kick in, real attraction kicks in, and around 10th grade – when everyone starts to drive – dating can quickly get more serious. While every family has their own rules and opinions, we all want our kids to make good choices. We don’t want them to date just anyone, because the quickest way to get off-track is through a bad relationship with the opposite sex.

And since this age is new to dating, they don’t have many good relationships to compare a bad relationship to.

So, what do you do when your son has a girlfriend that you don’t like? How do you respond when he’s crazy about a girl who is a bad influence?

Maybe she is wild and gets into trouble. Maybe she is manipulative, yet your son isn’t savvy enough to get it. Maybe she plays several guys once or has no parental supervision – no one to give her rules, or put on the brakes, or even give her a curfew, and your son gets annoyed and embarrassed because he has less freedom.

Or maybe you see changes in your son that concern you. Maybe he’s started lying, letting his grades drop, or caring less about school and activities. Maybe he shows more attitude or has neglected his friends because his girlfriend demands all of his time.

There’s so much you want to say, yet your relationship with your son already feels strained because this girl has caused division. If push too hard, your son may shut you out – and find his escape in her arms.

Every situation is unique, but I believe the starting point is always prayer. God loves your child more than you do, and He wants what is good for your son – like healthy, uplifting relationships – more than you do. He knows your son’s heart, his desires, and every thought inside his head. God knows what he needs from you today.

So go to Him with humility. Pray for guidance and wisdom. If this is truly a bad relationship, pray it only lasts for a short season. Ask God to open your son’s eyes and convict his heart so that he sees and decides for himself that this girl isn’t good for him. Ultimately, you want your son to make good choices for himself, not because he wants to please you. You want him to use good judgment when deciding who to let into his life.

So ask God give your son the strength, discernment, and clarity to make good choices, and if tough love is in order, pray about the best way to go about it. Just as importantly, pray for the girlfriend. Bring her into the picture as well.

Why? Because if she is on a bad track, there’s probably a reason. There is some pain, void, or insecurity that is the root cause of her behavior. Maybe she’s never had a healthy adult guiding her or modeling good choices. Maybe she has trauma from the past that stole her childhood or messed with her psyche. Maybe she fell into the wrong crowd because they were the only ones who accepted her when her friends ditched her or she made a big mistake. 

Even if the girlfriend is toxic right now, God can help her turn around her life. He is in the business of giving second chances and helping people get their act together, so pray for that to happen. Pray for God to use your son – during this hopefully short season that they’re together – to help the girlfriend grow in faith, find her purpose, and set higher goals and standards for herself.

After you pray, think about the conversations you want to have with your son. Ask yourself, how I can get messages across without him getting defensive? My opinion is that you wait for the right time. Be patient, collect your thoughts, and find the right opportunity so the conversation feels organic, not forced.

My friend Sissy Goff, an amazing counselor in Nashville, wrote a book with her colleague called The Back Door to Your Teen’s Heart. They point out that one mistake we adults often make when talking with teenagers is going through the front door. Instead of being subtle, we’re direct. We go in the front door and have conversations that can catch our teens off-guard and make them put up a shell.

In this case of the girlfriend, walking in the front door might equate to telling your son, “That girl you’re dating is bad news. You deserve way better and need to break up with her. Otherwise, she will ruin your life.”

If this is your strategy, your son may get angry or defensive. Not only have you insulted this girl he’s crazy about; you’ve also insulted his choice of girlfriend. With teenagers, parents go from a position of control to a position of influence, but what happens in front-door situations is that we lose our influence. We make our teenagers tune you out because now they don’t care what we think or say. They believe we’re against them instead of on their side, that we are the enemy they have to fight.

Even if your son had doubts about his girlfriend before, a front-door approach may feel like attack mode to him and force him into a position where he feels like he must defend the girl. This deepens the divide between the two of you.

Going through the back door means waiting for the right time to talk. Thinking of ways to be subtle and low-key – or as my mom friend puts it, ways to be a cat and not a dog. So often as moms, we’re loud and obvious. We just want to cross the conversation off our list – before we forget – and we’re not thinking about how it may be received.

A back door approach may look like waiting for a day when your son is in a talking mood. Maybe you’re driving him to basketball practice, and he tells you about his friend who just broke up with his girlfriend because she always gets jealous. You might nod and say that yes, unfortunately, that is a common mistake girls make. You had a friend in high school who did that; she had the best heart, but she always drove her boyfriends away.

From here, you might casually parlay into a conversation about what healthy dating looks like. Without even mentioning your son’s girlfriend’s, you can share what you’ve learned over time and ask your son what he considers a healthy relationship. If the girlfriend’s name comes up, ask your son what he likes most about her. And if it feels right, casually ask what he doesn’t like about her, pointing out how every relationship has two sides – and with each person we date, we learn what we can and can’t live without.

Keep your messages in mind and look for opportunities to share them. Rather than unload all your lessons and advice at once, share in bits and pieces. Use real-life stories or wise nuggets that fit into normal conversations.

And if you need some words to use, here are truths that I believe are helpful for sons to know:

#1: When deciding who to date, think about your future goals. Ask yourself, “Will this person help me or hinder me in reaching my goals?” It’s been said that George Bush gave this advice his children, and it’s a great way to get guys thinking about long-term aspirations, and who is the best partner for that journey.

#2: A healthy relationship will bring you closer to the people who love you most, like your friends and family. Any girl who creates division in your closest relationships – or tries to separate you or isolate you from them circle – really just wants to control you so you only listen to them.

#3: A good influence brings out your best. The right girls will inspire you to become the best version of you, to rise to the challenge and become the man you’re meant to be.

#4: Dating is about rejection. As a priest once told me, it’s about finding the 1 person you’re meant to marry. With some girls you’ll know on the first date whether you’re compatible –with others, it may take 6 months or longer to get to those hidden qualities that can make or break a relationship. Knowing this eases the sting of rejection and the heartache of breaking up because you know upfront that 99.9 of your romantic relationships won’t last, and that’s okay. That’s how it works. By keeping your relationships innocent, and not crossing the line physically, you can end on good terms and even be friends later on. You can treat your girlfriend like you hope somebody is treating your future wife: as her guardian, and not her lover.

#5: If a girl ever tries to come between you and God, then she wasn’t sent by God. God can only bless those relationships that draw you closer to Him.

#6: Once you realize you’re in a bad relationship, it is best (and easiest) to cut ties early. The longer you stay, the more complicated, emotional, and dramatic it gets. The girl will get more attached, you’ll get more attached, and you may stay together for all the wrong reasons and stop noticing the red flags.

#7: When you do date, pray for God to reveal whether this relationship is for a reason, a season, or a lifetime. Ask God to pick out the girls you should date and especially your wife, because as my dad always says, if you try to pick them out yourself, you’re gambling. Only God knows the future and who that person will become.

#8: Understand that some girls can be very sneaky and manipulative. They use their charm, beauty, or sexual power to get boys to do what they want. When you feel tempted, ask God to help you stay strong. Remember 1 Corinthians 1:13, which says that God will not let you be tempted beyond what you can bear, and when you are tempted, He’ll give you a way out if you ask.

#9: What feels like love is often just infatuation. And when you’re infatuated with a girl, you’ll put her on a pedestal she isn’t meant to be on. Blind spots will cloud your thinking. This is why it’s essential to listen to the people who know you best and love you most (like your siblings, best friends, and parents) when they express concern or doubt. Oftentimes, they see what you can’t see yet.

#10: While love says, “I can wait” lust says, “I have to have it now.” Your best rule of thumb in dating is to respect girls and treat them as you hope a boy would treat your sister. Anytime you bring a girl home from a date, she should be in better condition than when you picked her up. She should be a better person just by spending time with you.

Recently I heard an Andy Stanley podcast where he talked about not becoming your own worst enemy. He said: Don’t trade your future for someone who won’t be in your future. The bad influences in your life only be in your life for 2 to 3 years, and after they tear you down or undermine your future, you’re left with the ruins. So think about what you want in life, and then choose relationships that align with your values and goals.

Whether you’re raising a son or a daughter, speak the truth in love. Build a strong relationship so that they care what you think and listen when you speak. Pray for bad relationships to be short-lived and to teach them lessons, and remember we serve a merciful God, who is constantly working on all of us and hears the prayers of the faithful.

Whether it’s your son’s girlfriend or daughter’s boyfriend (or your child) who is not in a good place, God can work miracles. The big message of the Gospel is the transforming love of Jesus that changes us from the inside out, making us desire what He desires for us. Within this framework, you can pray for your children and their romantic interests, knowing there is hope for everyone – even those who need a major turnaround – and that the best relationships always begin when light finds light, when someone with God in their heart is naturally attracted to someone else who has God in their heart too.


Thanks for reading this message. Please share it on social media, or click over to the Girl Mom podcast to listen to it audibly.

My new book Love Her Well: 10 Ways to Find Joy and Connection with Your Teenage Daughter is now available, and it’s getting a fantastic response. You can find it everywhere books are sold, including Amazon and Audible. What a privilege it’s been to narrate my first book for moms!   

My two books for teen girls, 10 Ultimate Truths Girls Should Know and Liked, have been used widely across the U.S. for group studies. For more posts, subscribe to this blog or join me on FacebookInstagram and the Girl Mom podcast.





Posted by Kari on February 28, 2021

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One thought on "When You Don’t Feel Good about Who Your Son is Dating"

  1. Nancy says:

    Thank you for this article and reminding me God who is the source of love itself – loves my son way more than I can in my human strength. He has been with a girl now for over a year He was 15 when they started dating and he will be 17 soon. She has a lot of heavy emotional baggage like a dead father that makes me nervous for my son. I want him to be young and carefree and not that he has to try and fix her or help her. I feel she is substituting him as he is very mature for her father, boyfriend or any male influence she needs to fill the void of dad. So I find myself wishing it would be over. Please pray for me that I can continue to trust God, know when to speak and when to be silent and that I would pray also for this young lady and her heartbreak. Selfishly, I just wish my son didn’t have to be part of all that heavy in her life – but perhaps God knew he was just the right one for this season.

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