Things I Want My Teen Son to Know Before He Starts Dating

The dating world has changed a lot since I dated, but some things never change...

by Nancy Reynolds

This post: Things I Want My Teen Son to Know Before He Starts Dating

It’s all happening a little too fast for this mom’s heart. One minute, my son was playing with Nerf Guns and cracking fart jokes with his friends, and now he wants to start dating…

I guess I saw the signs coming and just didn’t want to admit it. His voice is changing, he towers over me and he’s been dropping subtle questions about dating. As much as I’d love to slow things down just a bit, my boy is ready to move full steam ahead in this new chapter in his life. And, like it or not… I have to get ready, too!

Even though my son is quick to tell me that I’m totally clueless about the dating world, “OMG mom, that’s not how it works!” – there’s still plenty of timeless advice I feel compelled to share with him.

Things I need him to remember.

Things I need him to understand.

Things I never want him to forget.

So before my boy enjoys all the amazing and beautiful experiences that lie ahead of him, including his first date, his first kiss, his first big dance or even falling for his first “real” love, here are a few things I want him to know before he starts dating.

Things I Want My Teen Son To Know Before He Starts Dating


Manners Will Always Be Cool

Like it or not, when you step into the dating world, manners really do count. Don’t be late, open doors, put your phone away, make eye contact and put your napkin in your lap. Also, don’t eat like you haven’t eaten in four days.

Remember all the manners I pounded into your head since you were three – use your knife and fork properly, don’t talk with food in your mouth, don’t slurp your drink, and don’t talk about yourself the entire time. Your date is noticing everything you do and don’t do… trust me. Make your mama proud!

Dress Like You Care

Whether you’re hanging out and watching a movie with a big bowl of popcorn, you’re going out for a fancy dinner or you’re hiking to the top of a mountain to watch the sunset, put your best foot forward and dress like you care.

That doesn’t mean you have to wear expensive clothes or try too hard to look perfect. What it means is that you should dress appropriately for the occasion, wear deodorant (pleeaaase), brush your hair and teeth, make sure your clothes don’t look like you slept in them, and wear shoes that don’t have mud caked on the bottom. Not only will you feel way more confident, your date will notice!

Don’t Worry About the Awkwardness

When you start dating, awkwardness comes with the territory. It’s pretty much to be expected. Don’t put too much pressure on yourself to act like a seasoned “dater,” when you’re just starting out. Instead, just be yourself, know that long pauses in the conversation might happen and that you AND your date might stumble a little.

To keep the awkwardness to a minimum, just remind yourself that everyone feels awkward when they start dating, plan a date that involves an activity (like a movie date, bowling, ice skating or maybe an amusement park) so you’re not staring at each other over dinner, ask lots of questions to keep the conversation flowing and know that not every moment has to be filled with conversation.

Show Respect… Plain and Simple

I don’t care if it’s your first date or your 50th, your date deserves respect. Be the chivalrous gentleman I raised. Be polite, kind and trustworthy. Keep your language clean, don’t ever flirt with others when you’re on a date, give your date your undivided attention, let them weigh in on what you do or where you go, don’t bore them about past experiences with “exes,” never demean them and don’t be “player.” I can assure you… no one likes a player. Also, go out of your way to compliment your date. Little things really do matter.

Always Remember the Rules of Consent

When you’re young, your hormones are raging and you’re crazy about someone or full out in love, it’s all too easy for things to move quickly in the relationship. Even though we’ve had this conversation dozens of times before, I have to bring it up again… always, always follow the rules of consent.

Don’t assume anything – a kiss or anything else, for that matter. Don’t confuse flirting or your date’s “sexy” clothes with an open invitation for sex. Remember that when alcohol (or any other substance) comes into play, it always muddies the water of consent. Of course, “No” means “No.” That’s a given. But you also need to understand that “No” can be conveyed non-verbally, and that “Yes” can be revoked at any time – no matter how far things have gotten.

Above all, don’t ever push your date, girlfriend or boyfriend into doing something she/he isn’t willing or ready to do. You hold NO CLAIM to someone else’s body EVER. Important NOTE: Don’t allow yourself to be pressured into doing something you’re not ready for either. (By the way, son… not everyone is having sex!)

Read: Teens and Sexual Consent: 8 Steadfast Rules They Need to Know

Cheap Dates Can Be Just as Fun and Romantic as Expensive Dates

There can be a lot of pressure to impress your date by dropping big bucks on expensive or extravagant outings. In fact, a nice dinner can set you back $50 – $100 these days! But don’t get caught up on how much a date costs. You can still have a blast, impress your date and be romantic even when you don’t spend a fortune. 

Take a hike, have a picnic by a waterfall or on the beach, skip the fancy dinner and go out for chocolate chip pancakes and coffee instead, grab a blanket and watch the sunrise or sunset, go stargazing, have a game or movie night or make dinner together. Casual, lighthearted dates are sometimes the best!

It’s Okay to Go Dutch

While it’s always a lovely gesture to pay for the first date, (in fact, I’m a firm believer that you should always pick up the tab for the first few dates), it’s probably not financially feasible to pay every time. After dating someone a while, have a gentle discussion about splitting costs sometimes or taking turns. Let’s face it, most teenagers don’t have a lot of money to spring for expensive dates.

Don’t Give Up Your Life

When you start dating, it opens up a whole new world in your life. Plus, it’s really fun! Suddenly, instead of playing video games with your friends on Friday or Saturday nights, you’ll be itching to go on a date with someone you’re crushing on. But, please… don’t get so wrapped up in dating that you put your life on hold or brush responsibilities aside. And, don’t spend every waking moment with your new crush.

You still need a life outside your relationship. Keep up your academics, hobbies, sports and time with your family. And, make sure you spend some alone time too to regroup and just chill. You need that time, son.

And… Don’t Give Up Your Friends

I’ve seen it far too many times. People get so caught up with their girlfriend or boyfriend that they push everything else aside, including their best friends who’ve been beside them through the best and worst times. Trust me… don’t do it. Nothing can hurt a friend more than being tossed aside like an old worn-out t-shirt. And, chances are, if you push them away too many times, they might not be there for you when you decide you want them back in your life.

Always make time for your friends. And, if your new girlfriend or boyfriend doesn’t understand how important your friendships are to you, it might be time to move on. If they care about you, they’ll care about what matters to you.

Take it Slow, Baby…

Pressure from friends, social media, and even your own intense feelings may make you want to move your relationship at lightning speed.

But sweetheart, you need to know that the best relationships start out as friendships. They’re marathons, not sprints. Let those feelings grow at a slow and steady pace before forging ahead too quickly and ruining it before it even gets started. 

Just Have FUN!

Of all the things I want my teen son to know before he starts dating, it’s to just enjoy the journey. Dating should be fun, not stressful! Plan fun outings, and get to know one another. Be silly. Be yourself. Be carefree! You may not realize it, but these are some of the absolute BEST times of your life. 

Above all, know that no matter what, you can always come to me. My door is always open to answer questions, offer advice or guidance or just listen, day or night. I’m right here, baby… Love always, mom (ahem…your first love).

This post was co-written by: Nancy Reynolds & Morgan Hill
About Morgan Hill:

Morgan Hill is an essayist and humorist. She has written for many online and print publications including Insider, Your Teen Magazine, Revel, and MASK Magazine. She is the mother of freshman and senior sons in high school. When not writing, she can be found at flea markets, in her garden, photographing architecture, taking cooking classes or eating the stinkiest cheese she can find. You can also find her on Twitter @MorganHWrites or Instagram @MorganHillWriter

If you enjoyed reading, “Things I Want My Teen Son to Know Before He Starts Dating,” check out these other posts!

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