Growing up as a teen in the 90s was the absolute best. I wouldn’t trade those years for anything. The untethered freedom to make mistakes with no chance of it ending up on the internet (a new weird thing back then that involved horrible screeching sounds and tying up the house phone)… Driving around in our old beat-up cars, blasting TLC and Snoop Dogg… Sneaking off into cornfields where no one could find us… 90s teens had it all.
Except (at least for me) what we didn’t have were essential conversations that would have made dating a whole lot easier.
Looking back, I know now that I made choices, decisions (and yes, mistakes) because I was floundering. I felt lost when it came to the physical aspect of dating. I’d hear about what other kids were doing (or what they said they were doing) and think to myself, “Well, I guess that’s what comes next” and fall in line, whether I wanted to or not. Whether this “next thing” felt comfortable for me or not.
I didn’t have boundaries. I didn’t have resources. And I didn’t know how to assert myself. No one ever talked to me about the word “consent” and no one taught me to know my own worth—especially when it came to relationships. Preventing pregnancy and being home by curfew—that was pretty much it for lessons.
I’m now the mother of a teenage girl, and she’s officially dipped her toes into the “dating” world of today. She is 14 and has her first “boyfriend.” As an 8th grader, here’s what that means: They message each other on Snapchat all day long. They hang out at my house or his house (an adult is always home). They’re allowed to watch a movie in the basement (with the door open) and there is definitely some kissing going on. (I know this because she told me and also because her her little brother has busted in on them a couple times.)
So here we go.
In lots of ways, this very cute and very exciting relationship reminds me of what I experienced at 14. My daughter walks around with her head in the clouds, beams from ear to ear at the mention of his name, and is 100% convinced that she’s going to marry this kid. I used to feel the same when I was young and in teenage love.
But there are a lot of differences now, too. For one, they have iPhones and Snapchat; I had the house phone (that I shared with my entire family) and passed notes at school. But another major difference is due to the fact that I’m approaching her dating years differently than how my parents approached mine. That means I’m talking to her about all of it—the good stuff and the awkward stuff—even if it’s uncomfortable. I do not want her floundering through these experiences, making choices she thinks she needs to make based on what her peers say they are doing. I do not want her to have regrets or do things that don’t feel right and natural for her. And I never, ever want her to question her worth as she moves through any relationships in her life.
So I’ve decided to have regular, continuous conversations with my teenage daughter about dating, and here are the topics we cover.
5 Conversations about Dating I’m Having with My Teenage Daughter (that I Wish Someone Had With Me Back Then)
1. You don’t have to go at the same pace as your peers (and also, FYI a lot of them are lying).
This is one thing I definitely regret about my adolescent dating years. I never felt comfortable and confident in using my own voice, in asserting myself, or in making my own choices about the pace at which I moved through each new stage of teen dating.
All I knew (or thought I knew) was what other kids were doing. And what my peers thought I should be doing, based on how long the relationship had been going on or what grade I was in.
For example, my first “boyfriend” (intentional air quotes here) was in 6th grade. Our entire relationship consisted of walking to home together from school, occasionally going to get an ice cream, and I believe he came to my house once and I went to his once too. There may have been hand-holding but it stopped there. And honestly, I was very comfortable with all of that. This “boyfriend” thing was exactly what I wanted as a pre-teen.
Unfortunately, everything changed at the middle school dance. Joey and I had been “dating” for a solid 7 months by then, and we hadn’t kissed, which everyone knew. And that’s why the dance I’d been looking forward to for weeks turned from a memorable night with butterflies in my stomach to a stressful evening with a slew of middle schoolers circling the two of us, chanting “KISS! KISS! KISS!”
Well, you can imagine how the rest of the story goes.
We did it. Everyone watched. It was awful. It was uncomfortable and, frankly, to tiny little 6th grade me, gross. And we broke up not long after.
That forced kiss was the end of our adorable middle school “love”, which was fine—nothing lasts forever when you’re a tween. But I regret that it wasn’t on my terms.
And I regret that I didn’t learn my lesson and still allowed peer pressure to dictate my dating choices for the next few years as well—mostly because I didn’t know how else to handle it. Each new “thing” that I was 100% unprepared for, didn’t understand, and usually did not want to do would come along as what I perceived to be the natural progression. From that 6th grade kiss to having sex for the first time many years later, I never felt truly “ready.”
“Well, I guess we’re doing this now,” I’d think and steel myself to get through it, hoping I was “doing it right” and accepting my discomfort as simply part of life.
It wasn’t until I met my now husband in college that I felt all the “good” things I’d heard about throughout my teen years. Only then did I feel sure of myself, of my own choices, and that I could do what I wanted to do—not what others were telling me to do.
And it’s because of these regrets that I’ve vowed to do better for my daughter. I will have the necessary conversations with her (the ones I wish someone had with me) about listening to her own self, listening to her own body. And that she gets to decide the pace of her relationship, not someone else.
Related: Parents Need to Take Every Opportunity to Talk About Sex
2. You can always change your mind.
Not only did I often feel influenced by the young people around me when it came to teen dating, but also, no one ever told me that I was allowed to change my mind. Like lots of girls (of all generations) I was taught to be polite. Don’t talk out of turn. Don’t make trouble.
And when you’re raised with those rules hanging over your head, you might find yourself alone with a boy who seems to be moving too fast. A boy you don’t feel comfortable saying, “Hey, I changed my mind” to. Because that would make you troublesome. That might make him mad. And you’ve been taught your whole life to not make people mad. So you go along with it and then live with regret that you didn’t assert yourself afterwards.
I’m teaching my teen daughter that she can always change her mind—about all things in life. Career paths, hobbies, interests, passions. And yes, any time she’s in a physical or emotional relationship, she is in charge of her own body and she can always, always change her mind.
And—this part is important too—if she’s with someone who doesn’t respect her when she does so, she needs to get out of there immediately and not look back.
3. If something doesn’t feel good or feel right, don’t do it.
Because I succumbed to peer pressure or what I perceived to be the appropriate “timeline” for different relationships I was in, there were many times I found myself in physical situations that didn’t feel good or right for me. I never felt physical pain, but more just a lack of… well, anything. Being physical with a boy often didn’t feel good, but it didn’t feed bad. It just was.
There were times I’d spend a make out session (that I wasn’t into) or, later, when it progressed to sex, just sort of waiting it out. I’d nervously hope a parent didn’t walk in, keep an eye on the clock, and think to myself, “So I guess this is it…”
When I started dating my husband in college and experienced what physical relationships are actually supposed to feel like for the first time, I was able to look back on all those times during my teen years that were less than pleasurable. What happened? What was missing?
I think there were a couple factors that contributed to my less-than-desirable teen and tween dating experiences—namely that things often moved faster than I wanted them to. It seemed like just when I’d settled in with comfort and enjoyment to something, it was time to jump to the next step. I’d go along with it, but I was always playing catchup in my mind.
Also, there was an actual teen love in there one or two times, but there were also a few boys on that list whom I dated for the wrong reasons. They were popular, they noticed me, and I was lonely or sad and looking to fill a void. But once the relationship started progressing, I realized I didn’t actually like them as much as I thought I did, and I didn’t know how to get out of it.
I’m teaching my daughter that if something about a relationship doesn’t feel right, it probably isn’t.
4. Know your worth.
We’ve all seen the movie clips of the shy girl falling for the popular boy. The girl who can’t believe some Brad or Chad—the captain of the team, the most sought-after boy in the halls at school—has chosen her to be by his side. And that glory can cloud a teenager’s judgment. Did it ever cloud yours?
My teenage daughter is an absolute catch. She’s outgoing, she’ll try anything, she’ll eat anything, and she has no fear. Biggest roller coaster at the amusement park? She’s already in line. Pickleball tournament downtown? Sign her up! She’s never played before, but she doesn’t care. Sounds fun! She’s down for whatever life’s adventures come her way.
But also, my daughter is kind and generous and has a very loving heart. At age 8, she asked me to send all her change she’d collected at an Easter egg hunt (amounting to nearly $20) to the World Wildlife Fund to help save endangered cheetahs. Last week, she took the dog for a walk and “set a new record!” (she proudly shared) for picking up 17 pieces of trash she found on the ground. And just yesterday, she told me that she complimented another girl’s outfit at school, adding casually, “I try to give 20 compliments a day.”
And she believes passionately in women’s rights and finds inspiration in strong female leaders. One day a couple years ago, she sat down next to me, late at night, wanting to show me a project she was working on (just for fun). “I started reading about powerful women in history and decided to create a presentation—one slide per person.” So far, she’d learned about pirate named Grace O’Malley and had also created a slide about Ruby Bridges. Next on her list was Ruth Bader Ginsburg.
She’s smart and has very lofty dreams—as she should. If you ask her what her life plan is right now, at age 14, it includes becoming a marine biologist, living in Costa Rica, saving endangered animals, and learning to surf.
And, she’s absolutely beautiful. Friends and relatives who haven’t seen her in a while are usually stunned when she walks in the room and frequently comment on how she’s grown up into such a gorgeous young woman.
I can see how much my daughter has to offer this world, so I’m determined to ensure that no one—no teenage boy, nor anyone else—diminishes her self worth. I will continue to talk to her about her own personal value that is not tied to this current (or any future) boyfriend, so if one day he’s out of her life, that she feels strong in her foundation and knows exactly who she is.
We also need to teach our girls about their self-worth so that when Brad or Chad does look their way, they don’t change who they are. I don’t want my daughter ever giving up her dreams or finding herself tethered down when she’s always been one to soar. And I don’t want her chasing some boy who isn’t chasing her back. I teach all of my kids to go where they are celebrated, not tolerated, and if they’re giving themselves to a relationship—any relationship—where they are doing the bulk of the work, where the effort is not being reciprocated, that they need to step back. They need to remember that they are better than that and to seek out relationships that fill their cup, not drain it.
5. State your boundaries. If he leaves, let him go.
Her first foray into the dating pool has led to many important conversations, including one about boundaries. We’ve talked a great deal about ensuring she still prioritizes her girlfriends. Not only should make sure to spend lots of time with them, but she should ensure it’s quality time (meaning not Snapping the boyfriend the whole time the girls are together).
Also, it’s important to take breaks from each other. 14-year-olds in romantic relationships should not be together 24/7. Taking breaks from each other allows for other passions and interests like sports, hobbies, extra curricular activities, homework, and family time.
Boundaries can mean a lot of things. They can include statements like, “I’m not ready for that” or “I’m spending the day with my bestie. Talk to you tomorrow!” And whomever my daughter is dating should respect those rules she’s setting forth, just as she should respect his.
Right now, she’s dating someone who spends a lot of time with family, friends, and plays sports. There are times he’s unavailable and she understands and supports that, and he does the same for her.
I will continue to teach her about honoring boundaries and, if there is ever someone in her life who doesn’t, that she needs to walk away and let that relationship go. When someone doesn’t respect healthy boundaries, that’s a huge red flag I want my daughter to spot immediately as this can sometimes be a precursor to teen dating violence and manipulation.
Related: Setting Boundaries with Love: 3 Tips for Managing Challenging Teen Behavior
These 5 conversation topics will hopefully instill in my daughter a sense of self-worth and offer guidance into what healthy relationships look like. I want her to feel empowered in understanding that she’s driving her own car on this road through life—not some boy. He might a part of her journey, but her choices are her own. And I want her to know that as she meets new people in life, and as new romantic interests and friendships come and go, that she deserves honesty and respect—no matter what.
I can’t go back and do my teen years differently, and I am grateful for the life lessons and experiences I had. But what I can do is this: I can do better for my daughter. I can have these hard, awkward conversations with her. I can talk to her about things I wish someone talked about with me. And I will.
Looking for an additional resource to help you navigate the teen years?
Check out You’re Not a Failure, My Teen’s Don’t Like Me Either by Whitney Fleming. Whitney’s book addresses the many challenges we face as parents today and how we can tackle them to have better relationships with our big kids.
Parenting teens and tweens is a tough job, but you’re not alone. These posts might help:
8 Ways to Help Your Middle Schooler Develop Healthy Friendships
Parenting in the Influencer Age of Toxic Social Media
Why Are Teen Girls Struggling So Much Right Now?
How to Protect Your Teen’s Self-Esteem When Life Pushes Them Down
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