Dating Advice for Teenagers (and everyone else too)

I’m now on the sidelines watching my third child go through the adventure of dating. She’s 17 and pretty darn particular about who she spends time with, especially when it comes to the possibility of an intimate relationship. My two other children are older, so I’ve been able to watch – and hear about! – how dating has progressed with each of them, and their friends, over many years. What’s become clear is that most teenagers have no idea about how to spend quality time with someone else and help create a great date experience. Is it an issue that’s more widespread and not limited to just teens? Yeah. But as my youngest comes home post-date complaining almost every time that it was “the worst date I’ve ever been on”, so it’s darn informative to listen to her complaints.

This then offers me a jumping-off point to offer up some advice to teenagers about how to set up a date and how to then act while on that date. Is this advice just for boys? Of course not. Does it apply if you’re on a date with someone of the same gender? Yeah, definitely. We’re all driven by the same wants and desires, regardless of who you envision as your ideal date or significant other. In fact, this advice applies to all relationships, whether it’s a best friend, a cousin you haven’t seen in years, or the person who makes your heart race when they smile at you as they walk into the room…


One of the most common areas where teens seem to trip up is that they are too tentative about planning. A dialog like the following (a pretty typical interaction for my daughter to experience, from what she’s told me) does not instill confidence that you want to really go on a date, become part of a team, and have grand adventures:

pen on calendar planninghe: “so wanna do something?”
she: “sure, what should we do?”
he: “I dunno. what do you like?”
she: “lots of stuff. what do you want to do?”
he: “idk.”

Instead, propose a plan. As with so many things in life, having a starting point is much easier than staring at a blank page or empty canvas. Try “wanna try that new taco place? Then maybe we can play frisbee in the park!” Not too difficult and you’re already miles ahead of most of your peers by proposing a specific plan.

Of course, being flexible is smart, so if she responds “ugh. hate tacos. how about pizza?” then it’s a chance to demonstrate your flexibility. A response like “cool, cool. mama madrone’s has sick pizza. tried it? love that place.” is clearly way better than “oh. um. then what?”

Question: Why should the boy propose the plans? Answer: Either party can propose a plan, of course, but based on dozens of teens I’ve heard talk about dating, most girls are hoping that the guy will indeed suggest a specific plan, even if it’s then tweaked and changed. Your mileage may vary, but regardless of who proposes it, a plan is always better than the endless “dunno, what do you want to do?” cycle.

Negotiated a plan, have the times figured out, and are ready to go? Solid. Now it’s time to actually meet up.


Dating Rule #1: Pay Attention to The Other Person.

That’s it. That’s all my advice. Everything else spins out from this basic rule. For example, your phone, your apps, your games, other people who are texting or “snapping” you are all now less important than the person with whom you’re spending time. It’s tempting as a parent to condescendingly complain about “kids today” who are on their phones instead of interacting with each other, but us adults do it just as often too. Next time you’re out and about have a close look at couples and groups; we’re all hypnotized by our devices nowadays.

boy obsessed with smartphoneIf you’re with friends, it can be companionable to be on devices together, and sharing a game or funny TikTok can be fun – these gadgets are becoming an important aspect of our lives, after all – but generally speaking, if you’re spending time with someone, you’re expecting them to be paying attention to you. And vice-versa; both people on the date should be putting down their devices and paying attention!

Tip: A fun challenge that a lot of adults do at social lunches is pile up their cellphones, screen down, on the table, then agree that the first person to check their phone has to pay for dessert, drinks, or the entire meal. It’s a smart and socially acceptable way to say “hey, pay attention to me” at a meal.

Dating Rule #2: Shut Up and Listen.

The corollary to the first rule is that if you’re making eye contact, sharing your life, ideas, and enthusiasms, you also need to make sure you’re not falling into the trap of being completely self-absorbed. It’s not about you. It’s about both of you. So shut up occasionally, ask open-ended questions, then let them have the time to answer.

This is when we circle back to my daughter’s latest date, where she told me that after spending over an hour talking about himself, the boy with whom she was on her date finally asked her a question about her life, then promptly interrupted her answer to basically explain how his life was better and more interesting. Did that endear him to her? Would that work with you?

woman listening

Tip: One great place to learn about the insidious nature of interruptions is at a local coffee shop. Pretend to read or look at your phone and just watch and listen to the conversations around you. Who talks? Who interrupts? Who’s the “alpha” in the group? They typically have the biggest ego (not a compliment in this instance) and are often actually driven by their insecurities, not their expertise. Remember that true leaders are excellent listeners.

Okay, so back to that date. You’re at Mama Madrone’s enjoying a small pizza pie with this person for whom you’re all fired up. Is it okay if you stop talking occasionally and they don’t say anything either? Is a silence of a few seconds – or longer! – acceptable? Yes, it is. It’s a chance to think (not a bad thing) and an opening for them to move to a new conversational topic. Also keep in mind that some people can be uncomfortable talking about themselves and their lives, so while you might talk effortlessly, they might just need more space to find the confidence to share part of their lives with you. A tough topic? Then that’s true x10. Be quiet and let them talk.

Dating Rule #3: Be Kind.

Assuming you’re listening and giving them the space to talk about themselves, it’s important to remember that you need to be kind too. If they’re sharing about a personal crisis they’re having with the latest assignment in their German class, it’s time to say something like “sounds tough” or “ugh, good luck”. If you dismiss their concerns and challenges, it’s not going to end well. “school is stupid” or “i’ve always found languages super easy” are going to land like a sock full of mud. Guaranteed, you won’t come across as the cool kid, you’ll be seen as someone who has no empathy. And that’s never pretty.

But being kind isn’t about pretending you care, it’s about changing your mindset so that you actually do care about what’s going on with your friends, family and, of course, your date. See “it’s not about you” earlier.

Dating Rule #4: Be Fun, Have Fun.

I suppose there are some people for whom life is always serious and they don’t ever smile or laugh, but for the most part, a first date is not the time to complain about your life. Eventually one of the characteristics of a good relationship is that you are mutually supportive as each of you go through the inevitable challenges and overcome life’s obstacles, but not on date #1.

incoming text message notificationsA good date should leave each of you happy, excited, and eager to see them again. That’s hard to do if you’ve just dumped a lifetime’s worth of problems on the other person in the previous 90 minutes.

I’m not saying you shouldn’t be candid and honest, but there’s a world of difference between a casual “yeah, my mom’s a pain in the butt sometimes.” and a ten-minute diatribe about how horrible she is and how it affects you every single day. oh, and how she’s across the room monitoring your date too. Creepy.

The adult version of this is complaining about your boss or your job. Truth is, we all have challenges and problems, it’s just a question of whether sharing them in detail is going to help the other person decide you’re fun and interesting or not. What do you think?


Survived a date where you practiced listening and learning about the other person and their life? Excellent.

After you’ve gone your separate ways, it’s entirely appropriate to send a quick snap or text letting them know you enjoyed yourself and are looking forward to the next time you’ll see them. Heck, you can even suggest the details of a second date, like “foo fighters livestream Fri night. wanna come over? I’ll cook!” though odds are pretty good that they’ll have to propose a reschedule.

Don’t forget that you can learn a lot about how they thought the date went by their response. An answer like “hate foo fighters, non-starter.” is not so good. “busy fri. what you doing sunday?” is good. “hated spending time with you, hope you fall in a sinkhole” is definitely not good, nor is “fallen in love. let’s run away and get married instead.”. 🙂

That’s it. In a word, pay attention to the other person and basically be the person on a date that you hope the other person would be too; fun, engaged, and completely focused on the here and now. Good luck!

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