How To Stop Dating Like a High-Schooler

On Valentine’s Day of my freshman year of high school, I went out on my first official date. The boy met me at a movie, carrying a stuffed teddy bear and heart balloons. I was 14, he’d skipped a grade and had just turned 13. He was almost a foot shorter than I was. It is a scene that mother, who watched from her car in the theater parking lot, has recounted through snorts of laughter a thousand times in the years since. That moment didn’t capture the years of high school and college that followed that he spent tormenting me with insults and sarcasm under the guise of being a class clown or a buddy.

Sophomore year, I went on what I felt like was my first date-date. The boy was older — 17! — and cooler and the experience oozed from him. I thought that meant he’d have a driver’s license, would pick me up in a car and probably even pay for the movie. Instead, he used every cent he had to take a cab to my house, asked my dad to drop us off at the theater, then looked to me dopily to pay for the tickets and snacks. You may think that this lead up and then the fact that, when a piece of popcorn fell out of my hand and landed on my itty-bitty boobies, he leaned over, plucked it up and ate it, would sour me on him. But no, I was smitten. And when he kinda-sorta asked me to prom later (and never did follow up by taken me), I still swooned some. I was disappointed in the less-than-romantic nature of it all, I wondered if my expectations were too high, but I liked him and I wanted to believe it was a good date. It was not a good date.

I know that now.

Many dates, boyfriends, casual relationships, one-nighters, crushes, living with someone, a long-distance romance, a big wedding, a marriage, a divorce, and many online dating profile iterations later, I know that was not a good one. Still, I’ve been at dinners with a middle-aged man and felt almost exactly like I did when I was fifteen, horrified at his manners and still wanting desperately for it to be a good one.

What’s different now is the voice of experience and confidence that tells me to politely say goodbye to the popcorn-plucker, prom-promiser and insulting Napoleon guys, to move on. And then to write about in a way that helps me move on from the dates that are a little too reminiscent of high-school characters.

That means I have written a lot about dating, have a lot of crazy stories about relationships started online, and have big opinions about leaping lipstick-first into dating, especially after divorce.

Part of the challenge of ending a long-term or significant relationship or marriage and returning to dating is that many of us hold on to the attitudes, practices and crazy ideas we conjured up in our 20s, in college, or well before when we first held hands in a movie theater with a short, sarcastic boy bearing balloons.

That’s not all bad — some of those dating ideals are sweet, some of those boundaries should stick. But keeping a death-grip on everything we thought about dating when we first started can also keep us stuck in a high-school mindset, not just about the whole concept of romance and relationships, but about ourselves.

We no longer have crimped hair and Sally Jesse Raphael red glasses (oh, just me?). We’ve lost the braces and obsession with Nick from Duran Duran (OK, some of us). We have enough life experience to know the legwarmers and neon would come back (and has). But it’s easy to go back to that place, to embody that girl when we are dating again. Unless we dig back to who we were and what we wanted back then and walk ourselves through to this point in our time, our dating habits, expectations, boundaries and even desires may not grow up.

Here’s how to shed the high-schooler and evolve into an age-appropriate dater:

First, travel back in time. Just for a few minutes.

I propose that we go back to the days of doodling hearts and entwined bubble-letter initials, to having our moms drop us off at Olive Garden in the family grocery-getter, to debating whether we are “going out” or just “going together”, to melting at the drop of Drakkar Noir and clicking over frantically on call waiting to see if it’s him on the other line to visit who were were as a dating young lady.

Close your eyes and envision when it all began.

Smell the Obsession, feel the newly sprouted mustache whiskers on the face of that kid on the wrestling team, feel the cloud of sweat surround you as you steamed up your Pontiac 6000 in the WalMart parking lot.

Then shuttle forward, counting each step.

With eyes still closed and focus honed, recall what it was like to be you as a teen and young adult. I think we have to really get in there, to remember what were like as a date to a dance, how we felt standing in line next to that one guy from Geometry at a kegger, what we told ourselves on that first walk of shame back to the dorm room, the burst-wide-open feelings as we brought someone home to meet our whole crazy family over Thanksgiving break.

From there, step into the 20s and bars and set-ups, maybe through to the first online (or free weekly newspaper) dating profile, to running into someone from high school on the train and exchanging numbers, to debating about how to text that one person for the very first time.

Bring yourself, slowly and surely, to the present. 

Step by step, make your way through the milestones and moments and relationships that brought you to where you are today.

What was your last date like? What you would you have liked it to be? When was the last time you shined with confidence, you felt gorgeous and sexy and brilliant and hilarious and fun with someone else? What supported you in being on fire in that moment? What can you call on, release, acquire, remember, tap into and jot down so that you can feel that way again?

Hold on to some of the past, let go of most of it.

Some parts of who you are romantically may be the same — I still absentmindedly doodle the Not Boyfriend’s initials when I am on conference calls and get a little giddy-shy when I hear him say my name on the phone. Delighting in liking someone feels good, and why should you put any more pressure on that? Have crushes, feel hopeful, daydream a little. Maybe stop at hiring someone to deliver a balloon arch so you can take prom-like posed photos together, but do let the birds sing and the the unicorns swoop over rainbows while you think about the object of your affections every once in a while.

Next, practice being an adult dater, even though stretching may feel a little uncomfortable. 

It’s also critical to affirm what has changed — beyond the red plastic glasses and not needing a ride from your mom all the time. Are you more confident in your curvy body than you were when the hips and boobs were first blooming? Are you attracted to people who have jobs they love and are invested in and passionate about (other than at Taco Bell, which was super-hot senior year)?  Do you have a child? Are you more reserved? Do you love a man who towers over you these days? Compare the kid you were with the woman you are and don’t just note the differences, give them a gold star.

Then throw in what’s hanging on from the high-school girl that could use some growing up, too. How can you strip off the shame from traveling back home after an overnighter? Why are you still squirmy when someone pays the bill? Are you ever going to go on a movie date again? What will it take for you to believe he will follow through if he asks to take you to some big, fancy event? When is it time to stop accepting insults packaged as humor?

Finally, shake off the life-coachy stuff, put on your good-ass jeans, order a glass of Chateauneuf du Pape and thank the goddesses you’re no longer a high schooler. Or dating one.

You can help yourself move into the present, to be an age-appropriate dater, to shake off the cringe-worthy moments and bad memories and wounds of all those early dates. It might not be a romantic magic cure, it won’t invite Brad Pitt into your bedroom and it doesn’t mean you need to look up those old beaus on Facebook. But you will feel more you — the you who you are now — the next time you’re on a first date. And you can always kick off the conversation by sharing a story about your very first official date (after you’re done with the popcorn).


Read more of Jessica’s adventures as a single mom in the city at Sassafrass.

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Ogle shoes together on Pinterest.



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