Teen Dating: 5 Tips for Talking to Your Teen

Teen boy and girl dressed for dance laughing

Just imagine. It’s breakfast time on a beautiful Monday morning. The sun is shining in through the open window, the smell of warm coffee fills the air. It seems like the perfect start to the week.

You call up the stairs to your 15-year-old daughter, “Come on down to breakfast, honey! We need to leave for school in 15 minutes.”

You expect the typical power struggle to get her out the door but are happily surprised when you hear her immediately begin marching down the stairs. 

However, your happiness is short-lived when she makes it to the kitchen. There in front of you stands your daughter–your little girl–wearing…is that makeup?

Honestly, you’ve seen this coming for a while now. You’ve noticed the eye shadow and smelled the perfume. You’ve listened as her conversations gradually shifted from school and friends to boys and…well…more boys. 

Still, it seems impossible. Wasn’t she just playing tea party with her dolls a moment ago? 

“Mom?” she asks quietly. 


“I was wondering if it would be okay for me to go out on a date sometime?”

And there you have it. The question you have been dreading since the moment you brought her home from the hospital has finally been asked.

Your daughter wants to start dating.

Of course, you want to shout “No!” But, because you’re trying to play it cool, you fight the urge to take her straight up to her room, wipe off the makeup, and lock her away until she’s 30. 

The truth of the matter is your daughter is growing up, which means having real-world, real-life conversations about dating is now a necessity on your parenting to-do list. 

However, if you’re like most parents of teenagers, you’ve probably had other important conversations that haven’t gone so well. You know the reality of tackling tough topics with a teen can involve a lot of eye rolls, sighs, and attitude. 

But, you know this topic can’t be ignored. More than anything, you want her to listen, because what you have to say about dating is important.

It’s no secret that your daughter is navigating some tough waters and will be for some time. The teen years are filled with hormone-driven dilemmas and you are going to need to be on the front lines, ready to help in a way only a parent can.

So where do you start?

First and foremost, you must establish a judgment-free zone.

That’s right. As much as it may pain you to do so, the only way you’re going to build trust with your teen is by providing them with the comfort and knowledge that what they tell you is safe from judgment from you or anyone else.

Now that the lines of communication are wide open, let’s talk strategy. Here are 5 tips for navigating this topic so you can ensure you and your teen get the most out of this very important conversation.

Establish a judgement free zone
1. Start Small. Start Early.

First and foremost, it must be said: It is never too early to start having conversations about dating with your child.

Because the mere concept of dating can range widely in interpretation from person to person, it’s important that your kids have a very clear idea of what they can expect from the dating world before ever stepping foot inside.

Now, as awkward as it may be talking about dating and relationships with your twelve-year-old, the conversations you have early on are critical. This is where you can dive in and gain a better understanding of what your child thinks dating will be like when he’s older. It also gives you a wonderful opportunity to lay some ground rules before he walks off hand-in-hand with his new crush.

Start small. There’s no need to get into the heavy intimacy discussion quite yet. 

Try asking, “What does dating mean to you?”, “What do you think happens on a date?”, or “What would be your idea of the perfect date?”

Perhaps, for your child, a date means hanging out with a group of friends, going out for ice cream, or riding bikes to the park together. Use this time to talk about how you get to know someone better and what qualities he will look for in another person when he wants to start dating.

Now is also the time to lay the groundwork for the expectations you’ll have for them when they do begin dating.

Will the date be chaperoned? What hours and days are they allowed to go out on? Will you meet their date’s parents first? When will they be allowed to go on car dates?

Setting the rules early on will not only provide you with a concrete plan to fall back on when the time comes, but it will also give your child less reason to push back down the road because they know what is expected of them.

Hopefully, you’ve been having these conversations all along. However, should you find yourself blindsided by a teen who is ready to, or already has, entered the dating world, here are some tips you can use to help take the terror out of teen dating.

2. Manage Expectations.

As tempting as it may be to launch into a long lecture on teen pregnancy the moment your daughter asks permission to date, it’s best to ditch the birds and the bees talk–at least for now. 

As you already know, having any conversation with a teen is tricky enough, so it’s best to start on a lighter note.

So here you are, the big question has been asked: Can your daughter go on a date this weekend? 

Your answer may come easily. A “yes” would certainly make your daughter happy. Moreover, a “no” would probably ensure your happiness. But try not to be so quick on the trigger–this is a big decision!

Instead, answer her question with some questions of your own. 

“Tell us about the person you want to go out with.”

“What is your idea of the perfect date?”

Now, the purpose of asking these questions is not to nag or pry, so try not to go overboard. This is simply a strategy for getting your daughter to open up about what she thinks dating entails and helping her manage those expectations ahead of time.

Having a clear understanding of what she wants out of a date will give her great insight into her own dating desires. As an added bonus, it will help you get to know her a little better.

Remember, this conversation should never feel forced, awkward, or uncomfortable for either of you. Take out the judgment, drop the inquisition, and, above all else, keep the lines open. 

Trust me, taking an active role in making sure your daughter is comfortable with the conversation now will pave the way for her to bring other issues to you in the future. 

3. Plan in Advance.

It’s a concept that seems old-fashioned to us, but there was a time when the perfect date consisted of burgers at the local diner downtown, an early movie, and drop-off at home by 10 PM. 

Yes, long gone are the days when teen dating was simple.

Now, when you ask your son about his upcoming date this weekend, you’re met with a slight shrug and a nonchalant, “I don’t know. We’re just going to hang out.” 

How frustrating!

Of course, this is a very typical response, especially for a teenage boy. Still, if you want to help lessen the dating terror–on your end, anyway–try encouraging your son to plan his date in advance.

Again, you want to proceed with caution, without encroaching on that nagging or prying territory. Keep the conversation light and aimed at helping him set out a plan for the date ahead. No need to be exceptionally detailed. Just try to help him answer a few important questions:

“Where will the date take place?”

“When will you be home?”

“Will there be any adult supervision?”

Also, think about a few different scenarios he may face and ask him to come up with possible solutions. 

For example:

“What would you do if your date suggests sneaking into her parents’ liquor cabinet?”

“How would you react if she lies to her parents about where the two of you are going?”

Giving your son ample time to think through his responses means he will be better equipped to handle these situations in a mature fashion should they come up. 

Yes, you can certainly expect to receive some pushback from your teen, but do not back down. Instead, remind him that dating is a privilege, and the only way he can expect to enjoy it is by having this plan laid out now. 

You’ll soon see that those eye rolls and attitude are a very small price to pay for your peace of mind.

4. Set Physical Boundaries.

In today’s society, particularly with the #MeToo movement, we have seen so many examples of men and women speaking up about their own experiences with abuse and sexual harassment

When it comes to dating, sons and daughters alike need to know well in advance what they consider to be their own personal boundaries. Knowing what their comfort levels are, how far they are willing to take things, and the consequences of their actions should be at the forefront of your teen’s mind when starting to date.

I get it! This is a difficult topic to approach. But trust me when I say having a conversation about relationship boundaries with your teen is absolutely crucial to ensuring both their safety and your peace of mind.

A few possible conversation starters may include:

“Tell me what you know about consent.”

“How do you feel about respecting your date’s boundaries?”

“What would you do if you felt your boundaries being pushed?”

As a parent, I know all too well how hard this conversation can be. After all, having your teen enter into the dating world opens them up to a lot of new experiences–some of which may not be ideal. 

Make sure you know which situations they could face that would make them even the slightest bit uncomfortable. Even more importantly, make sure they know how to get out of them safely. 

5. Come Up With an Exit Strategy

A particularly ingenious example of an exit strategy is what is known as the X-Plan

In a viral online post, one father, Bert Fulks, explained how he and his teen came up with a simple, yet brilliant exit strategy of their own. A simple “X” in a text message would be enough of a signal for Bert to come remove his teen from any situation that made him feel uncomfortable, compromised, or in danger–no questions asked! 

Parents around the world are now employing the same tactic with their teens. Not only does it provide teens with a graceful way out of any situation they are uncomfortable with, it also enables them to save face socially.

However, please remember that “no questions asked” means exactly that. Any and all conversations you have with your teen need to be done in a safe environment, free from any judgment or shame. 

When it’s clear to your teen that you love them unconditionally and will always have their back, you’ll find that these deep, important conversations become more open, honest, and frequent.

Final Thoughts

Navigating the teen dating world can be a daunting task for any parent. But there is no reason you can’t ENJOY this time as well!

By maintaining a strong focus on establishing trust and communication with your teen AND utilizing these strategies, you can absolutely take this journey from terrifying to terrific. 

For more information on this and other ways you can help your teen make the best decisions in life, please be sure to check out our other Positive Parenting Solutions resources.

Want to know if Positive Parenting Solutions is a good fit for your family?

JOIN ME FOR A FREE ONLINE CLASS where I’ll teach you how to get your kids to listen–no nagging, yelling, or reminding required.

As always, we wish you the best of luck on your parenting journey!

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About the Author

Amy McCready
Nationally recognized parenting expert Amy McCready is the Founder of Positive Parenting Solutions® and the best-selling author of The “Me, Me, Me” Epidemic - A Step-by-Step Guide to Raising Capable, Grateful Kids in an Over-Entitled World and If I Have to Tell You One More Time…The Revolutionary Program That Gets Your Kids to Listen Without Nagging, Reminding or Yelling. As a “recovering yeller” and a Certified Positive Discipline Instructor, Amy is a champion of positive parenting techniques for happier families and well-behaved kids. Amy is a TODAY Show contributor and has been featured on The Doctors, CBS This Morning, CNN, Fox & Friends, MSNBC, Rachael Ray, Steve Harvey & others. In her most important role, she is the proud mom of two amazing young men.