Love Letters: Playground Love & Dating Regrets

Love Letters

‘Love Letters’ is a Petal + Sass blog feature that regularly asks a group of diverse women in their 20’s and 30’s about their experiences with health, sex, emotional wellness, body image, college, careers – and what they wish they had known themselves as teenagers. Visit the Love Letters’ To My Former Self page to learn more about the contributors.

Question posed: Do you have any ‘dating regrets’ from high school? Did you date around, just focus on friendships, or have a long-term monogamous relationship? What would you tell yourself about dating in high school if you could do it all over again?

Miss Bluebells

Miss Bluebells

Miss Bluebells: I feel like ‘dating around’ is a thing people used to do in the 1950s. ‘Dating around’ in high school just meant being slutty, which I was not (which truly was no choice of my own, I really wasn’t approached much until my senior year. Late bloomer). I was also hung up on the same person that I ‘dated’ on and off for most of my high school career. I was a love-lorn brooder type who thought there was only one person I was meant to be with forever and I just so happened to find him on the same street in the summer of 9th grade (tragedy from the get-go.) I wish I had snapped out of it and focused more on my self worth. I don’t even regret that I didn’t date more people, more so that I was hung up on one person who really didn’t return my deep affection. Waayyy to deep for high school, looking back. Not that high school relationships aren’t important – because I actually think they set the tone for all of your future relationships and self worth to follow – but in high school you’re just existing in a microcosm of a world where options are limited and emotions are high. You’re kind of thrust together with people you have no choice but to try to make a life with. After high school, the choices abound and you suddenly realize that “philosophical compatibility” is an option much more satisfying than “same band instrument.”

I actually think that ‘dating around’ sounds awesome. I’d recommend that, as long as you put yourself and your friendships first and don’t get attached to what other people think of you. Which is too hard. In which case I’d opt for a sweet, mutually compatible monogamous relationship that ends over text messaging freshman year of college at the end of your first semester. Which is too easy.

Miss CallaLily

Miss CallaLily

Miss CallaLily: Like many many people out there, it took me a long time to learn from my mistakes. As a serial monogamist, I had many long term relationships, and spent very little time focused on myself or my friendships. I’ll always look at this as a missed opportunity. Working on yourself can be lonely at first, but becomes so much less so and is integral to having a good life.

One thing I did get right was always making sure my boyfriends were my friends. Always, always be great friends with your partner.

With few exceptions, I always dated people at least a couple years older than me. They made me feel mature and important. They could always drive first, buy beer first, and I just loved believing that being younger meant that they would take care of me. It took me a long time to realize that I was looking for maturity which can happen at any age for men (or not at all). I’m now dating the love of my life and he’s a full year younger – and he takes such wonderful care of me, and teaches me how to take care of myself, which is even better.

With few exceptions, I dated “misunderstood” guys. Some of these guys were depressed and uninterested in treatment. Some were “artists”. Some were “brilliant.” I saw these people as interesting and challenging and felt safe believing these things would ward off boredom. In reality, they were just terribly narcissistic – which is insanely boring. Don’t date narcissists ever ever ever.

With few exceptions, I would shy away from breaking up with my boyfriends until way way way too late. For a stretch of time, I would cheat on my boyfriends in order to force a break up. I don’t know what advice I could give to prevent this destructive habit.

Mostly, looking back I recognize that I learned from every relationship, so I know that they were important. The most important lessons that I’ve learned have been: Never tolerate a boyfriend who comes between you and your family, or one that makes you feel uncomfortable talking about the things you are thinking about, or one for whom you must make excuses to your friends for. People can be interesting and still be nice.

Miss Lilac

Miss Lilac

Miss Lilac: I grew up with good friends who are dudes, so I never really “got” that you were maybe supposed to act differently with guys that you wanted to date and those with whom you were just buds. (I still stand by the fact that the person I will end up with will appreciate this about me, but I definitely appear a little gruffer than most ladies). Once, I had a crush on a boy, and after a night of thinking I was playing it super smooth, I whitewashed his face with a snowball. That momentary victory (I mean, I won the snowball fight, hands down) was followed by a lifetime of cringing at that memory.

I think that that is a pretty telling tale of my high school dating experiences, which is to say there weren’t many. Like with most things, I was a late bloomer. In retrospect, I wouldn’t change a ton of it. I’m still very close with most of my guy friends from high school, and don’t think that that would be the case otherwise. The only real regret I have was that I got caught in a pretty bad love triangle (square?) towards graduation. I had pal’ed around with 2 guys and another girl, the girl was in love with Boy A, as I was with Boy B. Boy B expressed feelings for me. We dated without telling anyone really and I fell so so hard. We continued to pal around with the others, and then he broke up with me for the girl. Man, that was awful. More than the extreme feelings that raged in my adolescent self (I think I listened to a lot of Sheryl Crow acoustic to try to get through, that should probably be my biggest regret of all), it set a weird precedent for a number of under the radar relationships that I’ve had through the years. All of them feel pretty terrible. So the only real advice I have is if you are hiding a relationship, ask yourself why you are doing so, and if it is really making you happy? Whoever you are seeing should be proud to be with you; you are a BAMF. If you find yourself slipping into backrooms or erasing texts, think about yourself even if you think it’s real love. I hate to be the one to break it to you, but it probably won’t end up well.
Miss Magnolia

Miss Magnolia

Miss Magnolia: I usually had long term boyfriends in high school. It was a huge waste of time and I should have dated around and had fun. I was way too serious about boys in high school.

Looking back, I would tell myself to be more relaxed, and that you’re not going to end up with these boys forever. In fact, you won’t even want that in a few years. Enjoy the boys for the play things that they are at that age. You can get serious about them later when they’ve grown up some.

I regret making boys my main focus in high school. Also, you should know that not one boy is ready for marriage under the age of 30.

Miss Peony

Miss Peony

Miss Peony: In high school, I was involved in a lot of dramatic relationships. I dated this one boy for four years on and off. He was always cheating on me, and instead of leaving the relationship, I used that as an excuse to treat myself and other men badly. I dated several guys at once, cheated on my partners, and led on really nice guys. I rationalized my behavior, thinking that each drama-filled incident would be great fodder for my future career as a writer, but the truth is that I wish I spent more energy on academics and less on romance.

I slept with lots of different guys, but I didn’t really enjoy sex until my senior year of college, when I knew my body and myself better. Discovering feminism took intimacy to another level for me. Loving and respecting myself allowed me to love and respect my partners. You need to feel trust in order to let go and enjoy yourself completely. It was a great feeling to graduate beyond just giving pleasure to allowing myself to receive it. If I could give advice to a teenage girl, I would tell them to make sure they’re enjoying sex. Otherwise, why have it?

Miss Rosebud

Miss Rosebud

Miss Rosebud: Let’s be clear about what we’re talking about. Dating is different than being in an exclusive relationship, and it’s different from hooking up. It is less formal than the first, more formal than the second. Dating is fun. It is testing the waters. It isn’t something you obsess about.

When I was in high school, no one “dated,” and I don’t think you can at that age. First, the setup of high school makes it impossible. High school is a fish bowl; you can’t “date” someone that you see in gym class every Tuesday, Thursday, and Friday. Second, dating takes a hefty dose of emotional maturity, detachment, and control that as a teen, you are just beginning to sort out.

I felt like everyone was either in a bizarrely serious mini-marriage or they were just hooking up. The first seems harmless enough, but they should be spending the time with friends and doing whatever else it is that teens do instead. The second seemed concerning, and I don’t really know what to say about it.

I have no regrets about high school. I had a boyfriend, and we’re old friends now. College, I have regrets. During college and your early 20s, date around! Bring back the date! It is insane to be in a relationship if you don’t both seriously think you may get married, and/or if you have been with the person for longer than 2 years and aren’t engaged. Why waste half a decade of your life encumbered by the burdens of monogamy when you “aren’t ready for marriage” or “wouldn’t spend the rest of your life with this person for x, y, and z” or “aren’t sure”?

Read more topics of conversation from the Love Letters‘ Series.

2 thoughts on “Love Letters: Playground Love & Dating Regrets

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