Eleven Things I Wish I Knew About Love and Dating in my Twenties

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This is the longest I’ve been single in my adult life (one year, with periods of dating and a fling.) I’ve taken it upon myself to research love and dating, why we choose the partners we do (since, like many others, I was so very clearly choosing wrong,) and really just seeking answers to certain questions, namely: How do you have a healthy, lasting relationship? Do you really need to marry to be happy? Why do we find ourselves in unhealthy relationship dynamics? I don’t have all the answers to these questions, but I have learned a lot along the way.

In this past year, while at times it’s felt lonely and weird to be single, I’ve also discovered a tremendous pleasure in it. It gets worse before it gets better, as the saying goes. I’ve also dedicated a lot of time to evaluating what didn’t work, and my part in it, in an effort to not repeat the same mistakes.

We play a major part in choosing romantic interests, even if they are “toxic” and bring chaos and uncertainty to our lives. We are always half responsible for our relationships.

So, as I inch closer to thirty, I’ve had three long term relationships, a near engagement, several short term relationships, cohabiting twice, and everything in between, and these are eleven things I wish I had known about love and dating in my twenties:

Don’t Ignore Red Flags

Stop Photoshopping them a different color, honey!

Get really comfortable with walking away from red flags, and keeping both eyes open when you see a pink one. If the guy is an alcoholic, a gambler, a financial mess, doesn’t take care of basic hygiene, treats his mother or people in the service industry like crap, or disrespects you (or anyone else for that matter) it’s imperative you walk away.

Do not make excuses for someones red flags. Do not convince yourself you can fix or change him, no matter how good the sex is, or how much you want to be the fairy tale exception. You are wasting your time and causing yourself more hurt the longer you prolong this. Take it from me and many women like me, and walk away from red flags pronto.

Figure out What You’re Actually Looking For

This is the benefit of dating and staying single a little longer. You can take your time figuring out what you’re really looking for. To be honest, I’m still getting clear on that myself, but having that wish list and a few non-negotiables makes the process of dating a lot easier.

Make a list of qualities you’re looking for. If you don’t know what you’re looking for, you may settle for what you get, and get so wrapped up in being chosen that you forget to choose! So, figure out what’s important to you. Is it a sense of humor, ambition, an adventurous spirit, a desire to have kids? Write it down (aim for thirty qualities) so you can look back and evaluate dates based on what you wrote to keep perspective and perhaps make adjustments as you evolve.

Be flexible and open minded, and understand that while most people probably won’t meet all the criteria, that doesn’t mean they should be written off, and they may still meet most. Still, this is a good tool to ensure you hold out for a really good one.

Oh yeah, and ask yourself if you meet your own criteria. If you don’t, start working on yourself. Would you date you, based on the list you made? Check yourself before you wreck yourself. 

Take it Slow

Pump the breaks on commitment and imaging yourself married to someone you’ve been on two dates with. It takes time to get to know someone, and for their true character to be revealed.

We all put our best foot forward in love, even when revealing our so-called flaws to our potential partners, conveniently leaving out our chin hairs, commitment issues, inability to put the caps back on the toothpaste, or our closet smoking habits.

Let them and you reveal yourselves slowly and naturally.

Date More Than One Person at a Time

For the longest time, I believed this was a floozy thing to do, and I couldn’t understand how people got away with it in the 1950s. Here’s the kicker: you don’t have to sleep with them (you can, of course, just be safe and stay honest with your dates.)

Date light heartedly and get to know people! It will help shed light on what you do and don’t like, and what you will and won’t tolerate. Plus, it really helps from getting too obsessive and attached to one person and outcome.

Your Early Childhood Experiences Will Shape Your Romantic Future

If you grew up in a perfectly healthy household where your physical and emotional needs were consistently recognized and met, and you saw a loving, trusting, secure bond between your parents, you are lucky.

Many of us, God bless our parents (we know you did the best you could!) experienced a less balanced upbringing. So, if you experienced physical or emotional neglect, or saw addiction or alcoholism on the regular, screaming fights, or inconsistent care or a lack of boundaries, it’s extremely likely you will recreate these scenes in your romantic life in an attempt to heal them.

It doesn’t mean you’re doomed, though, if you make a conscious effort to learn about your past, devote yourself to self awareness, and maybe even go to therapy.

“You are a Magical Kitchen”

If you haven’t read The Four Agreements yet, get on that, but if you have, Don Miguel Ruiz wrote a follow up book called The Four Agreements in Love and the first one is that “You are a Magical Kitchen.” He goes on to elaborate that this magical kitchen can nourish your hunger, your soul, your emotional needs.

You walk into this kitchen and whether you want Vegan nachos supreme, a chocolate milk shake with a handful of maraschino cherries or a bubble bath and a hug, you got it.

The point is, we always hold the power to give ourselves what we want and need. The trouble starts when we put the responsibility of having our needs constantly met by someone else, and feel barren and hungry when they’re not met. Like, bitch, you are a motherfucking magical kitchen, what are you so hungry about?

It’s ok to have needs, and to expect your partner to be there for you, and respect your boundaries, etc. but the point is that if we seek for love to fill a void in us, we’re missing the mark. Love is what happens when our cup already floweth over. Learn to fill your own cup. 

In other words, learn to comfort yourself, and give yourself the entertainment, attention, validation, love, and nachos you so eagerly seek from others, cause you are a magical kitchen, baby.

Alcohol is to Men What Weed is to Snacks

Drink responsibly. Just like how weed gives us the munchies, alcohol gives us the mansies. Weed will have you lapping Hershey’s syrup off of tortilla chips just as alcohol can have you falling into the arms of a guy who doesn’t even brush his teeth twice a day. Be smart. Put Hershey’s syrup on ice cream and put that guy back in the “as if” box.

Drink responsibly, and date sober, at least some of the time, especially in the beginning. Alcohol can make boring events and boring people seem interesting, so you should really find out if you enjoy someones company while you’re sober before deciding to throw alcohol into the mix.

Don’t Fake Orgasms and Don’t Fake Feelings

I am shocked to learn this is still a popular tactic used among women who are either too scared to explain what gets them off, don’t know what gets them off, or really just want sex to end. Or, maybe more commonly, don’t want to offend their guy and want him to to instead feel like “the man.” 

You’re not doing anyone any favors by faking your orgasm or your feelings. Vaginal orgasms are a myth. Women come from clit stimulation alone, and vaginal penetration that results in orgasm is due to stimulation of the clit in the process.

Ladies, find your clit. Know your clit. Love your clit. Teach your man to do the same.
You do not have to be demeaning. He will most likely be stoked and when he sees what your real orgasm looks like, and won’t miss the off- Broadway show you were putting on before.

Please do us all a favor and learn to have a real orgasm with your partner. There are so many resources out there to help you if you don’t already know and coming is awesome and you should be doing it often so don’t sell yourself short.

You (hopefully) wouldn’t fake having feelings for someone, do don’t fake one of life’s greatest natural highs. 

Become Financially Independent and Thriving

When I was in my late teens and early twenties, I dated a couple of guys in the tech industry who generously foot the bill on vacations, food, and one who even “prorated” my rent for years.

At the time, it was great, but I stayed in a relationship years longer than I should have because I was scared that I couldn’t afford to make it on my own. I could have, and eventually did, but at the time it really didn’t feel like an option.

There are always ways to make money. There is so much money in this world and people get so stuck believing they are only entitled to the breadcrumbs. Get creative. Do research. Talk to people. Sell your in-demand skills. Ask around. Get certified in something. There are ways.

There was also a lot of guilt surrounding this financial arrangement I was in, and something my then boyfriend could always hold over my head. Again, I should have seen this as a red flag, but I didn’t know better at the time.

It feels much sweeter to spend your own money, and to make a life for yourself. It also means freedom. You should be with someone because you want to be, not because you feel like you have to be. 

There’s nothing wrong with accepting financial gifts or offerings from someone, in fact gifts and quality time are my love languages, but speaking from experience, get yourself comfortable financially for you. 

Relationships Are Not Always as Happy as They Seem on the Outside

This goes for anything, but please take those picture-perfect social media posts with a grain of salt and know that those couples fight, accidentally hurt each other, have power struggles, make sacrifices, and even question whether they should stay together or not, or perhaps wonder “what if…”

That’s not really social media worthy talk, though, and could get you the boot from your beloved pretty quick, so you don’t hear about it! Many people save their relationship woes for their therapist or journal, and only share the good parts with us. While that’s all fine and dandy and all, it can skew the view from the outside. 

Just remember to keep it real if you feel yourself lusting after some Insta-worthy relationship. Know that every relationship is filled with imperfections, and both of those people occasionally miss aspects of their single life, so enjoy yours while it lasts because it won’t last forever (and if it does, you’ll figure out a way to be happy, and those couples will still occasionally be envious of you from time to time, whether they admit it or not.)

Sex is Sacred

For real. Biologically, women are wired to become emotionally attached after sex, or even cuddling. Samantha Jones may be an anomaly, but she was fictional and most of us are better off with some discreet Amazon purchases (like the original Magic Wand and Jack Rabbit or even a detachable shower head) and being VERY discerning about who we choose to sleep with, because it is damn easy to just fall into a relationship with someone you sleep with because you will both likely become emotionally attached!

Sex is not going to be the ticket for the connection and intimacy and validation you’re craving without building that connection and intimacy and validating yourself first. Believe me, I’ve tried many times. It doesn’t work. 

Porn has become ubiquitous, and this is not a post about hating porn, or saying you shouldn’t have casual sex if that’s an experience you want to have, because our sexuality shouldn’t be repressed, but there is value in waiting, and this has nothing to do with a man valuing you more for waiting. This has to do with making smart decisions about our bodies and health, and choosing wisely who we decide to engage in the most intimate act possible with.

You do you, and I don’t regret how many tries it took me to learn this lesson, so if you need to find out for yourself through experience, by all means, have at it (safely and with discretion.) 

So there you have it, eleven lessons I’ve learned in my teens and twenties about love and dating. It took several heartbreaks, red flags, near-stalkers, break-ups, make-ups, hookups, bad dates, good dates, ok dates, flings, lies, betrayal, etc. to get here, but I made it through. You will, too. I’m still learning, and I hope you learn from your dating and love experiences, too, and stay hopeful even when it’s challenging. 

4 thoughts on “Eleven Things I Wish I Knew About Love and Dating in my Twenties

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