24 Things About Dating and Relationships I Want to Tell My Teenage Self

Surprisingly, when you’re in your teens you don’t actually know everything about love, romance, and relationships.

Sure, you know that you crying is often a bad sign, cheating and lying tends to rub people the wrong way, and condoms were made by the same people that invented jail. But aside from that, going into our romantically formative late teens and twenties, we mostly just went with what made us feel good, or what we gleaned from the relationships around us, or what we could kind of make out on the Pay Per View squiggly channels.

While there’s nothing necessarily ‘wrong’ with the learn-as-you-burn approach, we sure could have saved our older selves a lot of time, headache, and heartache if our current selves were around to sit our teenage selves down for a little chat.

So when we finally invent time machines, and they don’t accidentally turn us into hair gel, and they’re affordable for writers, from all the wisdom I’ve accumulated, here is what I plan to tell my teenage self over a cold beer and a few Party of Five episodes…

1. Don’t Waste Too Much Time Chasing People Who Don’t Appreciate You
Between falling in love with friends and running down shallow, unattainable floozies, you would do well to recognize that as long as you’re not a repulsive degenerate, there is a very finite amount of time that you should spend trying to convince people you’re worth their romantic attention; in most cases, that time is pretty close to zero.

2. There Really Are “Plenty of Fish in the Sea”…You Just Suck at Fishing
There is no shortage of people out there; you just have to figure out how, where, and when to apply your energy to create the right opportunities. And you will. Unless you move somewhere weird and small, like Liechtenstein or Vatican City…then you might be screwed.

Besides, there’s also chicken, beef, pork and tons of vegetables.


3. You’ll Never See Everything Coming
Don’t get in the relationship game if you can’t handle surprises; good ones and bad ones. If you’re looking for predictability, rent an Adam Sandler movie.

4. You Are Not Entitled to Closure
This is not Friends; this is The Sopranos. Wait, you haven’t seen the Sopranos finale yet? Right, that wasn’t ‘till 2007. Well, what I mean is, don’t expect to get all the answers. That doesn’t mean you should be confused; it means you should readily accept that some information, you’ll never have. And trust me, you’ll live without it.

I need to find the most scenic place to be alone.

5. Wear Clothes that Actually Fit
Being comfortable is important; but so is getting laid. You don’t need to wear spandex, but you certainly don’t need to dress like an X-Games lumberjack or a pregnant rapper. Unless you are actually pregnant, in which case we should probably watch Junior again.

6. It’s All Personal, But Don’t Take It All Personally
Yes, people can be very selfish, and yes, indirectly that is personal, but seriously, a lot of stupid stuff people do is much less deliberate than you think. And to be honest, if you’re hoping that everyone thinks you’re important, you should get out of the love business and get into the music business. Sometimes it is you and not them; just chill, and work on deciphering the difference. And…

7. Improve Yourself All the Time
This doesn’t mean you’ve done something wrong, it means you’re doing it right. You should want to be getting better all the time; at everything. Remember that practice makes perfect. Well, not “perfect”, but at least better than a lot of other people, and at the end of the day, it’s all relative.

8. Dude, You Have NO IDEA How Much Porn There’s Gonna Be
Ok, admittedly not an “indispensable” insight, but it would have been really interesting to know.

Oh..um…I didn’t see you there…

9. Being “Critical” Is Healthy; Being Negative Is a Pain In Everyone’s Ass
Thinking critically and challenging the reason and value of things around you is part of being a conscientious, contributing member of society who wants things to constantly get better. But that does not mean you have to go around pissing on people’s parades. It’s a subtle balance, but an important one to master.

10. Don’t Ever Tell Yourself “I Know What I Want”
You’ll ignore a lot of solid opportunities if you don’t accept the fact that while you think you know what you want, you’ll probably be surprised at what actually works. Not to mention that many of your “tastes” will change. Like Liv Tyler? You’ll be over her in a month. Téa Leoni stays pretty hot though.

11. Don’t Have Too Many Deal-Breakers
“Likes Country Music”, “Can’t Cook”, or “Eats Gelato While They’re on the Toilet” might sound like appropriate reasons to count someone out, but in the big fat scheme of things, they’re not. Get good at distinguishing between “inconveniences” and “sources of fundamental relationship stress”, or you’ll spend way too much time trying to fix everyone but yourself.

12. Your Standards Might Be Irrational and Unrealistic
You go right ahead and shoot for the stars, but don’t act like a brat when people tell you to aim for a few streetlights too. You will hear people say, “Never Settle”. Ignore them and spend more time with people that tell you to “Be Reasonable”.

Just remember, you might not be as good at jumping as you think…

13. Never Underestimate the Importance of Sexual Appeal
Usually, it’s very very very important. Yes, eventually all that fades when everyone gets old and smells like a dusty attic, but until then, sexual satisfaction and the desire to “jump someone’s bones” is something you should never take lightly. You’ll know exactly what I mean when you end up dating that stripper in 2010. And the one in 2011.

14. Give People Space to Like You
Not everyone is quick to make a decision, and though unfortunate, people tend to easily generate and panic over self-inflicted stress. So work on being a nudger, not a shover.

Maybe try a true or false question?

15. Don’t Be an A**hole with Response Times
I don’t care what some limp-witted, flakey narcissist tries to tell you, just reply to people’s messages as soon as possible, or as soon as it makes sense to you. If you scare someone off because they confuse “courtesy” with “desperation”, or they punish you for being excited, believe me when I tell you that you’ve dodged a bullet.

16. You Shouldn’t Lie, But Shouldn’t Always Say Everything On Your Mind
Colonel Jessup was right; people can’t handle the truth. 95% of the time that someone says they want to know everything you’re thinking, they’re either lying or they’re wrong. The other 5% of the time, they’re a rare breed of rational, or they’re f***ing drunk.

When the wine starts talking, you probably need to slow down.

17. Don’t Make People Feel Bad About Themselves
You are entitled to voice your sentiments and try to get the most out of your relationships. But when you do, focus on making people better, not making them feel worse. You should never encourage insecurity and self-loathing; that’s what Sunday nights are for.

18. People Change Their Minds A LOT, And Usually, Don’t Even Make Them Up in the First Place
If Michael Jackson didn’t teach you this lesson, your next 3 girlfriends will. You can’t avoid it, and seldom will you understand it. But you will have to accept it. And quickly.

Too literal?

19. Give People The Confidence To Be Honest With You
Never make it uncomfortable for people to tell you like it is, because each unique perspective, to some degree or another, is the way it is.

20. Before You Give Advice, Try to Make Sure They Actually Want to Hear It
Sometimes, people need an ear, not a brain. And if over time, they prove to not value your brain, start using your legs.

21. Only Be With People Who Are Naturally Supportive and Considerate
Someone who is always in your corner and consistently thinking about your happiness makes all the difference in the world. Sense of humor, charisma, talent, popularity, professional ambition, or robust genitalia will never be substitutes and will not sustain a relationship. Shocking but true.

22. Try To Admire People For What Required Courage & Character, Not Genetics & Geography
You should always be most impressed by the achievements that required a great deal of judgement.


23. Patience, Patience, Patience

24. Rewrite This List Every Few Years
It will come in handy. I promise.