At 31 years old, I’ve been dating for quite some time now—my twenties were a storied history of unsuccessful relationships and sexual encounters that have often left me feeling, as my Jewish mother would say, “meh.”
Nonetheless, I’ve held out hope that my dream man is out there somewhere, waiting patiently. I have no idea who the hell he is, but I do know he makes a mean brisket, loves getting weird on the dance floor, and thinks a solid Saturday morning is rubbing my feet while watching hours of Rick and Morty. He’s also a heavyweight champion at head.
Still, i’ve been single for over a year and it’s as dry as the goddamn Sahara. I’ve swiped through all of NYC so thoroughly I think I’ve actually reached the end of Tinder. My friends are tired of me complaining, my mom’s pawned me off to the sons of everyone at temple, and I’m this close to buying a cat, rubbing it all over my face (even though I’m allergic), and just calling it a day.
The only place I haven’t turned... is to the kids. Like, actual kids. Perhaps their non-jaded, pure-hearted spirits know something I don’t about why my dating life is literal garbage.
Do I just need to send more pictures of my boobs? Should I be communicating in nothing but emojis? What’s Jaden Smith’s advice? How can I slay? Are we still saying fleek?
I told them to be ruthless. I told them to spare nothing. I told them I was their humble student, laid bare at the hands of their expert guidance.
And they straight up blew my mind.
Meet our teen experts: Alyson, Rachel, and Aaron from San Diego, California.
Hey everyone! Why don’t you start by sharing a bit about yourselves. Who the heck are you young people?Aaron: I’m 17 and a senior in high school. I really enjoy writing poetry about my feelings and I’m addicted to wearing Adidas sweatpants.
Alyson: I’m 17 and a senior in high school. I write for magazines. I love Teletubbies and colorful socks and I’d like to go to college on the East Coast.
Rachel: I’m also 17 and go to school with Alyson and Aaron. I love literature and soft socks.
You guys live in California, why the hell are you wearing socks?Rachel: Socks are a huge thing here!
All right then! First question. Where’s the best place for me to meet men?Rachel: I don’t know if it’s me and my Cali lifestyle, but I think it would be great to meet guys at a coffee shop. Like, an alternative coffee shop. You know, do work and hang out.
This sounds like the beginning of a '90s sitcom. What generation are you even from?Aaron: I think you should meet men at places that already interest you—so you both have something in common to chat about. Go to a place that makes you feel nice and do it for yourself. You’re not going to find some guy at a bar.
What about online dating? Isn’t that where the young folks are these days?Alyson: I don’t personally have Tinder. I know some kids my age that do. My personal opinion is that we all want a “we met someplace” romantic-type of story.
Rachel: I think online dating is good up to a point. I know Tinder is a place for hookups. What about Match.com?
Match.com?Rachel: It’s taken more seriously. Tinder is just a bunch of people throwing themselves around.
Point taken. Okay. Real talk. Do you guys look at me as an unmarried 31 year old and think “Wow. She’s super lame?”Alyson: My parents got married around your age but honestly, I haven’t thought a lot about marriage. I don’t want to plan my life out though, if It happens, I’m not opposed to it. But I think this is a great time to being “doing you” at 31. You’re living in New York and being cool. Just be Ariana.
Rachel: I would like to get married by 27, but it’s also really important that I get my doctorate so I’m going to be in school for a long time. Being 31 and unmarried—there’s no judgment there. You’re living life to the fullest. You’re a great writer. I don’t think age really matters.
Wow. Can you guys be my three-person therapy team?Aaron: Sure!
When do you think is the right time to have sex with someone? I’m pretty comfy having sex off the bat. Is this a good strategy?Aaron: It’s all in your own judgement. I personally haven't gone all the way—though, I’ve gotten close. You decide what’s right in the moment. For me, I decided I didn’t want to do it. The truth is, I’ll have sex when I want to do it and my partner should be able to respect that and wait for me.
That is an incredibly mature and empowered way to look at sex. I’m very impressed.Alyson: I haven’t even kissed anyone yet. A lot of people misconstrue it as being prude, but I just take it really seriously. How am I going to feel about myself after? A lot of kids at our school are sexually active. You know about "Netflix and chill," right?
Yes. I’m not a million years old.Alyson: It just depends on what you want to do.
Okay. Example situation: right now I’ve been on a few dates with someone and he’s good on paper but I’m just not feeling a click. Do I go on a few more dates to feel it out or end it?Alyson: You gotta trust your gut. When I think about being a single girl in New York, I think of Law and Order—be careful out there!
Thanks, mom.Alyson: Seriously though, theres going to be someone that’s perfect for you that’ll fit your puzzle piece. I don't want you to settle for someone that only fits the piece a little. Then the rest of the puzzle will be out of whack.
That’s some deep shit, guys. Thank you! So... how should I end it?Aaron: Well, you might as well be honest because it might be the last time you're talking to him. Don’t leave him with a bad impression of you. As long as you’re straightforward, he should understand.
How do you feel about me ghosting?Alyson: Aaron has a real thing against ghosting. I’ve had to do it a few times. It’s not that I’ve had so many suitors, it’s just that I thought we were friends and he kept trying to hassle me to be something more.
Rachel: I did it once in 8th grade. I’m not going to justify myself—it was bad. If it was done to me now I’d be super pissed. You’re so focused on the other person and then they leave you on the side of the road.
I have to say, I thought the kids today would be all about the ghost. I’m pleasantly surprised here. Speaking of past selves, would advice might you give to your younger counterparts about dating?Rachel: Not worry about it. In the past, I focused way too much on, “Ooh does he like me? What do my friends think?” I could have been playing Pokémon or something.
Alyson: I literally looked up facts about the World Series just to impress this guy I was into. I was just poring through Wikipedia, looking up things to talk to him about. My advice would be: don’t base your life on someone’s else’s. Don't pretend to be interested in baseball.
I think “don’t pretend to be interested in baseball when you’re not interested in baseball” is fantastic advice and also a great metaphor for life itself.Alyson: Thanks!
Wrapping up, do you guys have any questions for me?Rachel: (giggling) You don’t have to answer if it’s too personal.
Girl, please. Ask.Rachel: What’s been the best part of having a sex life. This is something I haven’t experienced yet—so what was it like for you?
Do you want my real answer?Rachel: Yes.
Well, it was pretty terrible until my mid-to-late twenties. Sex can be strange and uncomfortable and I didn’t feel like I could ask for what I wanted in bed until I felt more empowered as a woman. I certainly didn’t feel that sense of autonomy at 18.Alyson: Another question—what’s the biggest misconception about finding a boyfriend?
You have to love yourself first. When you’re younger, you think that if you can find someone to love you, he’ll teach you how to love yourself. It only works the other way around.Alyson: Thats how I feel all the time. That I’d be better if I had a boy.
I know. We’re socialized to play into the "damsel in distress" narrative—but it’s total bullshit. You gotta be be your own boyfriend—if that makes sense. Only then can you add another human into the mix.Alyson: (giggling) Also, we were wondering.. we’re super nervous about kissing someone. Do you have any tips?
Don’t wrap up your self-value in how it goes. It’s going to be weird. The first time you do anything is going to be weird.Rachel: Whew. That’s a relief.
It’s been absolute pleasure and seriously, you all give me hope for the next generation. Thanks for helping Stella get her groove back. I’m going to take your incredible advice to heart.Rachel: Anytime!