What I Learned From My Two Failed Lesbian Relationships

Dating Lesbian Couples Relationship Advice

What I Learned From My Two Failed Lesbian Relationships

I often like to ask Chia a lot of hypothetical questions about our relationship (i.e. Does she think we would still be together if we were living in the 1950s? Would she still like me if I had 6 toes? 😅).

I’ll admit that sometimes they’re silly and make no sense. However, Chia takes these questions very literally (for example, when I’ve asked if we’d still be together if we lived in the 1950s, she’s told me that we wouldn’t have met in the first place because dating apps didn’t exist back then 🤦🏼‍♀️) and therefore, is no fun. 

Nevertheless, I have still wondered what it would’ve been like if Chia had been my very first girlfriend.

I’d like to believe that we would still be soulmates the way we are now, but in hindsight, I’m glad that Chia and I met when we did–at a time when we had both matured and learned from our previous lesbian relationships. 

Prior to Chia, I had two other long-term lesbian relationships that as you could’ve guessed, didn’t work out. I’ve talked previously about one of them in my post about long-distance lesbian relationships.

The other one was my very first lesbian relationship back when I was in high school. It lasted over a year and then became an on-again-off-again type of relationship that wasn’t healthy for either parties (more on that later). 

Here’s what I’ve learned from both of these failed relationships:

1. Even if you love someone, they can bring out either the worst or best in you.

What I Learned From My Two Failed Lesbian Relationships

The first ex that I was in a lesbian relationship with (let’s call her “L”) was definitely not my healthiest relationship to say the least. It was a continuous roller coaster ride where I would experience extreme highs and then extreme frustrations. 

It often felt like a game of purposely making each other angry or jealous and then making up.

Being young and not feeling comfortable enough to be open about our relationship during those days certainly played a role, but we were also just fundamentally different people with completely different life perspectives and trajectories.

While we “loved” each other at the time, L certainly brought out the worst in me (anger, rage, jealousy, apathy, etc.) more often than not.

On the other hand, Chia, the love of my life, constantly brings out the best in me.

2. You can’t change the other person.

What I Learned From My Two Failed Lesbian Relationships

In my second lesbian relationship (let’s call her “X”), we had been close friends for many years before officially dating. So in a sense, I knew X really well and I was aware of the red flags and our flaws.

While our long distance didn’t make our relationship any easier, I thought that I would be able to change her into the person that I wanted her to be and the girlfriend that I wanted to be seen in public with.

After all, I thought I knew her better than anyone else and even better than she knew herself. 

But when you focus on trying to change the other person or waiting for them to change, it never really works out the way you want it to. Instead, you end up with both parties resentful of each other. 

3. Don’t ignore the red flags.

What I Learned From My Two Failed Lesbian Relationships

When you’re in the courtship phase, it’s easy to let the hormones kick in and ignore everything else. 

With L, we had a strong physical connection and in the beginning, we just couldn’t get enough of each other. But beyond the physical aspects–our life goals, ambitions, expectations, etc. did not align. 

Even though there were many red flags from the things she would say, I deluded myself into thinking that either 1) I can change her or 2) she doesn’t really mean what she’s saying and it’s not a big deal anyways so I’ll just ignore it for now.

Don’t let the honeymoon phase blind you to the truth.

4. Every relationship is a valuable experience, especially when you’re young. 

What I Learned From My Two Failed Lesbian Relationships

I’ve always thought that the advice/rule that some parents (especially Asian parents) give to their kids about not dating until you get to college and then marrying the first person you date is impractical.

I generally believe that the more experience you can gain–albeit safely, within reason, and not at the expense of your future–the better you understand what you truly want in a relationship and what you’re looking for in a life partner.

Would I still be who I am today without my prior relationship experiences? Perhaps. 

Do I have a better sense of what I want and what makes a healthy relationship as a result of these experiences? Absolutely.

This doesn’t mean you should say yes to every relationship and person who asks you out. The point is to not be afraid of them even if you don’t have the future all figured out and to learn from each relationship you have.

This brings me to my next point.

5. Your first relationship is not necessarily your last relationship.

What I Learned From My Two Failed Lesbian Relationships

Even though I knew early on that my first relationship with a woman wouldn’t last (we were in high school after all and the probability of ending up with your high school sweetheart is very low), I don’t regret being in it at all. 

I would still rather have been in that relationship than in no relationship at all and to learn through that process than sit around waiting for the “perfect” girlfriend to come along. It would be like choosing to have no job at all simply because it’s not your dream job.

While you shouldn’t go into all of your relationships being pessimistic, it’s important to be honest with yourself when it’s not working out and understand that it’s ok if your first few relationships aren’t your happily-ever-afters.

It’s ok if your first few relationships aren’t your happily-ever-afters.

6. Don’t lose sight of your big life goals and don’t let anyone hold you back.

What I Learned From My Two Failed Lesbian Relationships

Regardless of what relationship I was in at the time, I never lost sight of my academic or professional goals in life. This is especially important if you’re young and still in school or just starting off in your career. 

While I made time for my relationships, I wouldn’t be afraid of saying no to going out if I had a big exam coming up. Or when I had a once-in-a-lifetime opportunity to live and work abroad for a year that was aligned with my larger career goals at the time, I knew I couldn’t give that up or else I would end up resenting my partner at the time.

All relationships require some give-and-take, but if your partner is a bad influence or is jealous and unsupportive of your success, then it’s better to say goodbye than to let them limit your potential. 

7. Happiness comes from within. 

What I Learned From My Two Failed Lesbian Relationships

This is one of those life principles that I fundamentally believe in.

If you aren’t happy with yourself, no partner, no matter how great they are, can make you happy. And likewise, if you can’t find happiness within, you won’t be a good partner to your significant other either. 

In my second relationship with X, while I thought that we had a happy relationship, she wasn’t happy internally with herself and as a result, her personal insecurities and pessimism would project themselves onto our relationship. 

8. Don’t reinforce bad behavior. 

What I Learned From My Two Failed Lesbian Relationships

Inevitably, anyone that you are in a relationship with will annoy you from time to time (and you’ll annoy them too!). Most times, you’ll get over it quickly and it’s not a big deal. 

But if your partner displays behavior that you don’t like or that makes you feel uncomfortable, you should nip it in the bud as soon as possible. 

I made the mistake of not voicing my concerns with X with certain things that she would do and that only reinforced the type of behavior I didn’t want. For example, whenever we would get into arguments, she would bring up every grudge from the past no matter how old or irrelevant they were to the conversation. 

Instead of calling this behavior out, I’d try to use the same tactic as well. Unsurprisingly, keeping tabs on your partner is not healthy for either party in the relationship.  

9. Don’t mistake jealousy for flattery.

What I Learned From My Two Failed Lesbian Relationships

I certainly made this mistake often when I was younger. In hindsight, in my first lesbian relationship, I’d often mistake L’s insecurity and jealously for flattery. Whenever she would get irrationally jealous about something or someone, I would interpret that as her showing how much she cares about and loves me. 

I’d tell myself, “She’s only jealous of me talking to that person because she loves me and doesn’t want to lose me.”

In reality, this was a sign of a lack of trust and an unhealthy need for control in our relationship. And it only added more fuel to the fire. 

There are so many better ways of showing your love and appreciation for someone than through expressing jealousy.

10. Find someone who’s on the same wavelength as you.

What I Learned From My Two Failed Lesbian Relationships

Even though they say “opposites attract”, it’s important to be on the same page with your partner.

To use a nerdy analogy, there are two types of sound waves–constructive and destructive.

What I Learned From My Two Failed Lesbian Relationships

When you have two wavelengths arriving in sync together, they amplify sound (constructive).

On the other hand, when you have two sound waves going in inverted directions, they cancel each other out (destructive)–this is how noise cancelling headphones actually work. 

You want the former, not the latter in a relationship. 

While you don’t need to have the same exact friends, hobbies, or outlooks on life, when I was dating L, we were on completely different wavelengths in all of those categories from the start. Hence, after the honeymoon phase, our relationship was always rocky. 

On the other hand, with X, we were on the same wavelength for many things, likely due to the fact that we had built a strong close friendship beforehand. In comparison, my second lesbian relationship was a hundred times better than my first and lasted longer as well. 

11. You should be able to have intellectual conversations after the sex is over.

What I Learned From My Two Failed Lesbian Relationships

No matter how great the sex is, you can’t just have sex all day, everyday. At some point, you and your partner will have downtime where you’ll have to engage in conversation with each other so if they’re not interesting and can’t carry an intellectual conversation with you, the relationship won’t last very long. 

I came to learn this lesson really quickly with my first ex where I couldn’t enjoy being with her beyond our physical connection and things only unraveled from there.

12. Lust is not love. But love isn’t everything either. 

What I Learned From My Two Failed Lesbian Relationships

Don’t mistake lust for love. When you’re in lust, you focus on things that are more superficial (i.e. they’re attractive, popular, like the same hobbies, etc.). 

When you’re in love, you see a deeper layer of that person and despite knowing their secrets and flaws, you still feel like their presence warms your soul whenever you’re with them. 

But just loving someone isn’t enough either. I “loved” both of my exes from my two failed lesbian relationships, but it didn’t mean that we were compatible as life partners. 

There’s a lot more to choosing a life partner and you can read more about that in our post here.

13. Be with someone you’re proud to bring home.

What I Learned From My Two Failed Lesbian Relationships

Last, but not least, having been closeted for most of my life and during both of my lesbian relationships, I had a high bar for deciding when I would come out and share my relationship with my family and friends. 

I was never proud to reveal my relationship with L to close friends or family, which was already a sign that things weren’t going to work out. 

With X, I finally came out to my closest friends, but I never felt ready to come out to my mom about our relationship. There was still something that I felt was lacking in our relationship in order for me to take that step.

However, with Chia, everything changed. Not only did she get along easily with my best friends, but within the first month of dating, I wanted to come out to my mom about our relationship and ready to accept whatever reaction she would have. 

Chia was perfect to me in every way and I felt that I had finally found someone that not only I was proud to be with, but I was proud to tell everyone else that I was with. 

I had finally found someone that not only I was proud to be with, but I was proud to tell everyone else that I was with. 

And that’s when I knew that I had found the one after all of my previous failed relationships.

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