Lessons From Dating Around

Growing up, I didn’t really know much about love or dating. While the adult figures in my life were trying their best, their example left me with a pretty skewed knowledge of what was normal and what wasn’t. My lack of awareness led me into a pretty disastrous relationship in my early 20s that I’m so lucky to say has ended and that freedom has completely changed my life.

For the first time in my life I could focus on my own needs. It all felt like a second chance at life that I didn’t want to waste.

At 23, I started my life over completely with the goal of discovering what healthy love was—for myself and with others. I had an eat-pray-love journey, moved towns, got a new job, and really invested in my self care. For the first time in my life I could focus on my own needs. It all felt like a second chance at life that I didn’t want to waste.

I wanted to let my experiences and lessons teach me, so I could welcome nourishing relationships in my life. After a year of being single, I decided to put myself back out there with a new outlook. I needed more experience, so I decided to go on dates—a lot of dates. I downloaded all the apps and said yes to date opportunities that came my way. For about three months I went on at least a date a week and once, even two dates in one day *cringe*. I learned a lot about myself and what I wanted in the process; here are the main takeaways.

1. Be honest 

At times I was tempted to go on another date or stick it out with someone I knew deep down I wasn’t compatible with, but I learned no one benefits from this. Even if you want to like someone, you can’t force yourself to, no matter how good they might look on paper. It’s better to be upfront and honest after a few dates about what you want. If you want (or don’t want) a long-term relationship, don’t be afraid to tell someone. The right person for you won’t be turned off by you expressing your needs and wants. You can also avoid harder conversations later on. Be honest and be yourself.

The right person for you won’t be turned off by you expressing your needs and wants.

2. Say “no” more

Once when I was in high school, I said no to a boy who asked me to be his girlfriend, and then changed my mind after he started crying (spoiler alert: we broke up). It’s easier to say yes to spare someone’s feelings, but this won’t set the stage for healthy communication or a satisfying relationship in the long run.

Saying no will help you set boundaries, and it helped me feel empowered and more confident in my decisions. I learned I didn’t have to engage or give out emotional labor when I didn’t want to, and it allowed other people to be responsible for their own emotions. Don’t let anyone pressure you to move too quickly or do anything that makes you feel uncomfortable: anyone who values you will respect your boundaries.



3. Know your core values

If you want a serious relationship, it’s helpful to know what your core values are. These values are the guiding principles in your life that influence how you see the world, like religion, morals, politics, gender roles, etc. I didn’t know certain things were absolute deal breakers for me until I started having so many conversations with new people.

I didn’t know certain things were absolute deal breakers for me until I started having so many conversations with new people.

I realized which political core values regarding human + civil rights and environmentalism that I wanted a partner to share with me. It was too exhausting for me to be expected to completely educate a reluctant date-prospect on such heavy topics, and I found it easier to date someone who was already somewhat aligned on these big things.

While you can date someone with different opinions, it’s a lot harder to be with someone with radically different values or views on humanity. Be brutally honest with yourself, can you picture yourself with someone who has different views on gender roles or religion? Are you hoping you can change this person? Don’t go into a relationship trying to change someone; you wouldn’t want someone to change you. Also, the older we get, the less likely someone is to budge on what’s a core value for them. Know your core values and what’s a hard no to save yourself time.



4. Trust your gut

If you get a strange feeling about someone, trust it. Sometimes these feelings come up as early as messaging back and forth on a dating app. You don’t have to meet up with someone if you’re getting a weird vibe, or even give out your number. Listen to what your intuition is telling you. I once had a feeling a guy messaging me on Bumble had a girlfriend and it turns out he did—and she looked very eerily similar to me. Thank you, next.



5. You are worthy of a healthy love

The truth is, no matter what you’ve been through, you still deserve a partner that thinks highly of you and treats you with respect.

This was the most important takeaway for me. One of the motivating factors for staying in unhealthy or unproductive relationships is the lack of awareness of what you deserve. The truth is, no matter what you’ve been through, you still deserve a partner that thinks highly of you and treats you with respect.

That means you deserve a partner who won’t fall off the face of the earth for weeks at a time and then resurface. You deserve someone that communicates with you regularly and normally, regardless of how commonplace spotty communication has become. You deserve someone who puts in as much effort as you. There’s no need to perform mental Olympics to justify someone’s sketchy behavior, no matter how much you wanted it to work out. Find someone who’ll treat you with respect and choose someone that nourishes your soul and fills your cup.


When you start to truly see yourself as the imperfectly beautiful prize that you are, you’ll know regardless of any external validation that you’re worthy of a good thing—and that’s well worth the wait.


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Leah Thomas is a contributing writer at The Good Trade with a passion for wellness, inclusion and the environment. She works on the communications team at Patagonia and is a sustainable living blogger at Green Girl Leah. You can connect with her on Instagram @GreenGirlLeah