Cautiously looking for love

Organized Chaos
5 min readSep 7, 2020

As more of my friends turn 30 I feel like I’m asked to give advice on how to enjoy being single or even how to approach relationships. The first part makes loads of sense, I’ve now spent 13 years being single depending on how you describe that. Yes, I’ve dated multiple women for at least 5 months but those never progressed into a long term relationship. The second part is always interesting, even though I do talk to my friends about dating and relationship topics on my podcast I don’t think that qualifies me to give advice. Everyone who has visited and spoken to me has their own experiences both good and bad. There is a lot of work and communication that goes into relationships and I just feel that everyone looks for the easier path to maintaining a relationship and there is no simple method to be happily in love.

Photo by Priscilla Du Preez on Unsplash

I was talking with my friend last week and the question that gave me pause as we drank in his balcony was “have you ever been in love?”. It felt weird saying no but it was an honest answer. My only “relationship” was when I was 18, I was excited that someone was interested in me but saying I love you multiple times was based on a childish perspective. We didn’t really know each other, honestly, we were more infatuated with the other person but love takes a while to develop. We started our relationship because we were both interested in each other and knew each other but that doesn’t equate to love. Knowing her for a while and even post-breakup, I never had animosity towards her and even happy that she found love.

I spent my 20s going on many dates, some lead to no second dates, multiple dates which lead to either of us not having an interest in the other person. Many swipe rights lead to no conversation, ghostings, and best of all three great friendships. Some lead to hookups, some lead to longer times dating but never having the commitment attached to relationships. I don’t use my being an only child as a reason for my uber singleness, but I just had my own goals I wanted to accomplish. That’s usually always a cop-out answer but it’s true. I didn’t work on my mental health, wasn’t where I wanted to be career-wise to bring someone else into my life. I wanted to travel, go to baseball games, scuba dive, take classes, and get to do whatever I wanted without worrying about what a partner would think. My emotional unavailability and constant need to deflect questions that made me uncomfortable meant that I just wasn’t ready to commit. Also, I had some misconceptions about what relationships entailed looking back at it. I had this mindset that partners were codependent and that’s something I did not want in my life.

Found on the Internet

Settling wasn’t an option, I didn’t want to get into a relationship because I felt like there was this checkmark I had to accomplish. There’s this one quote I saw Tumblr in my early 20s, where it was the decade to be your selfish years. I took that quote to heart because there were just many things I wanted to do and I wanted to do so on my own terms. I didn’t think about having kids so there was never a rush to be in a relationship. I felt my life wasn’t together yet, I was taking temporary roles as I continued to spend my money on experiences.

Now that I’m close to turning 32 and still not saying I’m ready to settle right away but I do want to see myself in a relationship and I guess in a way I should put that out there in the universe. I’ve spent almost three years making a podcast and almost two years in therapy being able to deal with my own childhood trauma and a better understanding of my own behavior. The podcast has been eye-opening, it’s been great hearing everyone’s experiencing along with having great authentic chats about difficult relationship topics. I want to be able to have those kinds of conversations with a partner. Therapy has helped me open up and be more emotionally vulnerable, I know I’m not an open book but definitely more willing to have those talks.

Telling people I am open to a relationship leads to the next question which is “What are you looking for?”. Honestly, I can’t give a clear cut answer considering I’m still learning more about myself. I have a better mindset that I don’t want kids and now that I’m in my 30s I don’t want to waste someone’s time who wants to start a family unless it’s a family with dogs and cats. Considering how open I’ve been talking about depression I definitely want a partner that understands that she shouldn’t be there to fix me (something I thought in my 20s), just someone to be supportive and wants to understand the process. Dating in my early 30s has been productive, sure they didn’t lead to relationships but there were better open conversations. I also realize having a podcast may throw some women off but those episodes have been a self-assessing experience. I’m someone who enjoys my space and alone time for creative or mind-clearing escapes. Interdependency is something I’ve read about and would hope that is something a future partner would understand and like to strive for. There are other values that I can’t think of at the moment but the beauty of dating is getting to know people and the more questions I ask the more I’m better suited to figure out what it is I want to see in another person.

I’m going to approach this with a patient mind, there’s honestly no need to rush into a relationship especially during a pandemic. Sure, the need for companionship is important and feels needed when we have to social distance and wear masks. This is the perfect opportunity to engage in more self-work, build on the connections I already have. I think people tend to want things to work out so much that they accelerate the dating process and when it comes to emotions I’m going to be cautious and the goal is to start being more optimistic. Sure the paradox of choice makes it impossible for people to make decisions but I love the idea of knowing when you know. What made some short dating “relationships” work is that we didn’t rush it and enjoyed each other’s time. We realized that our values didn’t match, understood that, and moved on. That takes time and we live in a rushing, time-sensitive society. We need things easier, quicker, and better and that doesn’t help with online dating. I look at it with my closest friendships, those came from time getting to know each other and I believe the same approach should be had in relationships even though they’re different. When people who have been married for decades tell me my approach is the smart mindset I’ll take that feedback as a win and just continue working on myself and being cautiously optimistic with what a future relationship will look like.

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Organized Chaos

Podcaster. Baseball lover and already visited 20/30 stadiums. I write about social media, mental illness and whatever comes to mind at the time