What I’ve Learned about Dating in my Later 20s as a Hyperindependent Woman

A fun, sobering reality and trail of thoughts from someone dating intentionally in her later 20s

by thefanggirl

I can’t believe I am saying this, but I wish I dated more when I was younger. Through dating, I would then only learn more about myself, what kind of person I needed (not just wanted), and to understand the deeper complexities of finding a life partner. I never wanted to be one of those girls in a relationship, just to be in the sake of one. I was always focused on myself and building my own path forward, with little to no regard for men except when I started my last year in college.

I have also been quite independent, made good financial decisions growing up, and relied on myself for most things—maybe too much to a point where I now need to learn how to make space for someone in my life. I spent my early 20s working in tech, traveling and working abroad, as well as building businesses and going into content creation.

Strangely enough, no one really cared as much as they did about my dating life. As I came back to Bay Area from Asia, the slew of questions began. How’s dating? Are you excited for being 30? You need to date more.

Comical, but annoying comments from my older sister would come through time and time as she kept casually mentioning her 35+ year old friends who were still single. It was a sobering moment, when I realized that I did not want to end up alone and find myself only to be in a small pond of men who had low EQ, toxic, or divorced (not that anything is wrong with them). Suffice it to say, the chances of dating and finding quality men are much better when you’re younger. As I have jumped into the ocean (with arms flailing, but having fun) to find a life partner, these are the interesting things I’ve been learning about while dating intentionally.

You’re single until you’re not 

Thank online dating, but situationships are more common than you think they are. Due to the unlimited swipes and hoping for “something better,” people sit in a grey area of “what are we?” but are too afraid to ask. I was dating someone for a while, made the effort to check in with him about being exclusive and he said he wasn’t sure, while wanting to date other people. That was fine with me, but after two months, I realized he may have just wanted the benefits of being in a relationships without the label. I said my goodbyes and firmly walked away. Some friends said I should have waited more, but in reality, I also didn’t like the person I became with him, which was an Emily who was unsure, worried, and anxious. If I wanted to be with someone, I wanted to feel secure and happy, not wondering if he was dating 5 other women at the same time.

So basically, the idea comes with…just because you’re dating someone does not mean you’re in a relationship. Until the relationship has been clearly defined, you are single until you’re not.

Check out some of my necessities when I go out on these dates! Pepper spray and hand sanitizer for sure.

Mature, effective communication is communicating your needs, not expecting him to read your mind

I also realized how immature I could be sometimes, and it has taken a lot of self regulation and inner work to work through my irritations or when I’m a bit reaching. While I can be patient with friends, for some reason, my expectations of a partner are high and this causes rift when my needs aren’t met, but I haven’t clearly discussed it with the person I’m dating. After another kerfuffle and ended texting situation, I was talking to a close friend who told me I needed to communicate better. “They’re going in blind. They have no idea who you are, what your preferences are, and what you’re thinking. You need to tell them if you’re feeling a kind of way.”

This was good for me to hear, as my first reaction is to end things because expectations were not met. As I date more, I have been articulating my needs more and if it cannot be met, this match is not right.

What I realized I actually need

I admit, I am one of those girlys who wanted to date a 6 ft man.

I stand at 5’7 myself, and would have liked to date someone taller, ambitious, successful. But those qualities may come with other by-products, like business, curt, impatience, etc.

Most recently, I have been more open minded about the men I date. While I date guys from all backgrounds, sizes, and shapes, I realized that these resume characteristics aren’t going to be helpful when we have children, marital fights or disagreements, or when I’m feeling at my worst.

It is kindness, compassion, patience, and hard-to-find values that will keep a relationship alive and thriving. These are the important qualities to find in a partner, not the guy who is hot and cold, but charming.

It is his thoughtfulness of bringing me my favorite boba when I have a shit day, his willingness to take the dog out or take care of the baby when I’m on my period, or covering the bill and being like “I got this” than always splitting 50/50. I would contribute as well, but I am still old school as I’ve seen the way my father takes care of my mother and dotes on her. I want that too.

I still believe in chivalry and the guy being able to provide if need be if I am 8 months pregnant and stumbling around with a watermelon belly. I am a contributor, but I wouldn’t date a man who wasn’t caring and chivalrous in his actions because that would be telling to me how he would treat me down the future.

You’re not perfect, so you can’t expect him to be too

No one is going to be perfect right off the bat. You must understand that you’re bringing two different people together, with different upbringings, values, boundaries, personalities, everything. For a proper, healthy relationship to build, you need a lot of communication, compromise, inner work, and respect. I used to be quite toxic in the way where if a potential partner didn’t “just get it ” or didn’t meet a certain standard, the potential relationship was off; I would think, “I’m not even going to bother.”

I strongly believe that you attract the energy you give off, so it was a lot of self work and asking myself too, “Am I someone I’d date myself? Do I have all these good traits and strong values that I want my partner to have?”

Am I kind, patient, understanding, and there’s one that I see this on the internet a lot: do I bring him peace? Do I make his life better or happier? It also works the other way too. Is he bringing chaos or peace to my life? Does he make my life better?

I am definitely not perfect, so I wouldn’t expect my partner to be either. The “perfect” person simply does not exist, but the “right” person does, and that’s through a partnership of working through things together, communicating, and loving each other along the way. That is what I’ve learned.

Books I read to learn more about dating and myself

Photo by How to Not Die Alone: The Surprising Science That Will Help You Find Love

How to Not Die Alone: The Surprising Science That Will Help You Find Love 

This “simple-to-use guide” (Lori Gottlieb, New York Times bestselling author of Maybe You Should Talk to Someone) focuses on a different decision in each chapter, incorporating insights from behavioral science, original research, and real-life stories. You’ll learn:

  • What’s holding you back in dating (and how to break the pattern)
  • What really matters in a long-term partner (and what really doesn’t)
  • How to overcome the perils of online dating (and make the apps work for you)
  • How to meet more people in real life (while doing activities you love)
  • How to make dates fun again (so they stop feeling like job interviews)
  • Why “the spark” is a myth (but you’ll find love anyway)

I really like her style of writing, as it’s digestable and makes you question all the things we were taught about love.

Photo by Marry Him by Lori Gottlieb

Marry Him: The Case for Settling for Mr. Good Enough
In Marry Him, Gottlieb explores an all-too-common dilemma—how to reconcile the desire for a happy marriage with a list of must-haves and deal-breakers so long and complicated that many great guys get misguidedly eliminated. On a quest to find the answer, Gottlieb sets out on her own journey in search of love, discovering wisdom and surprising insights from sociologists and neurobiologists, marital researchers and behavioral economists—as well as single and married men and women of all generations.

[Additional Note from Nov 17, 2024] I Found a Good Man

I felt like it was fitting to add a personal update here since I’ve begun blogging more on my website.

Fast forward to end of 2024, I’m sitting on a cozy couch next to my wonderful man who is currently laughing at an anime series. We’re in “parallel play,” where we both do our own things while close to each other. I’m in a happy relationship with a man who cherishes me, takes care of me, is emotionally mature and available. All of those terrible dates have led me to him.

When I reflect on the person I was when dating, the one thing that stands out to me is the self regulation and growth that had to take place. I can’t think my best with this anime playing in the background, but here are a couple things I’ve learned that hopefully make you feel better about dating.

  1. Love shouldn’t be hard ~ if he’s making you suspicious, worried, angry, crying, or any of the negative emotions, revisit why you are with this person. Love should feel like a warm hug, you snuggling under the covers on a cold day and a cup of hot coco he made for you without asking.
  2. Figure out your boundaries and what you stand by. This helps you filter your future partner faster. If you know you want to date a man who’d be a good father, find someone who loves kids and is patient. If you date someone who always complains about children or doesn’t want kids, then filter him out. Do this early on, so it’s not painful in the future.
  3. Understand what a healthy, good relationship looks like. I was shocked to find out that two of my friends have been emotionally abused this year, only to find out that their boyfriends treated them terribly when they started questioning themselves, their integrity, and their own boundaries. I felt like both of them were being chipped away, almost to the point where the man would dictate everything and anything, including money, wardrobe, communication, etc. Please, please understand and look into what a healthy relationship is.
  4. If it doesn’t work out, it just means you dodged a bullet. Things don’t work out for a reason, and it’s better to close that door rather be in a 10 year marriage with kids and you realize you’re miserable years down the road.
  5. Good people are hard to find these days; it’s sad to say, but when you want someone genuinely great, you need to take in account the whole picture than just a couple resume attributes. If you want someone great, you need to be great too. That’s why a lot of relationship coaches always tell their clients to also work on themselves, meaning going to the gym, leveling up, working on their EQ, and becoming a better potential mate. This is really important, especially for women. A guy who is amazing will have many options.
  6. Love your person well. I mean it in the sense where love doesn’t just stop after getting into a relationship, or after any big milestones. Love your person every day, and especially when it’s tough. Love is an action, where you continue on working on that love, giving love to your person in the way they want, and working through the hard parts because you chose to love that person and want to be with them. Love may fade over time if not through action; I see it as something that needs to be practiced, maintained, and continuously being learned as you both evolve. Love is undying, it’s patient, it’s funny, it’s warm, it’s the person you want next to you all the time.

[Update 31 July 2025] I’m engaged!

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