How To Feel Better About Your Dating History—And Future

July 21, 2022

Okay, so I don’t know how you’ll feel better about your dating history, but here’s a trick that works for me. I simply describe each person from my past as if they were the most wonderful human on Earth.

You see, my complaint was that whenever I thought about my dating history, I felt as if it were all a big failure. I had acted dumb. I had gotten horny for guys who weren’t the Prince Charming I had imagined. It had all just been a series of “random” OKCupid hookups and “goofy,” pointless crushes on whoever.

My negative thoughts consisted both of judgments against my own behavior, and evaluations that these men weren’t good enough for me to have felt that way or to have spent that time with them.

So to counteract this, I started telling myself a different story about the guys I had liked or been on a date with. They were each so unique and beautiful in their own ways. It’s a privilege and accomplishment that I was able to spend time with a human being like that.

So much of how we feel about our lives so far is just the story we tell. The same life story can seem like a failure or can seem hugely accomplished depending on how we interpret. Yes, your mind might be tempted to go back into complaint mode, but you don’t have to obey that temptation. You can practice focusing on the parts of memories that are actually redeeming, and pretty soon everything starts to look completely different. It’s magic.

As for me, I started by thinking back to my high-school crush. I was going for a walk while thinking about this. I imagined reminiscing about all of his features that I admired. As if I was telling a friend about it—the perfectly placed mole on Leonard’s face, the way he would lean back in his chair and almost fall over… The boy used to play this unique game on the school grounds, which involved flicking bottlecaps. It was so entertaining to watch. Now if anyone ever asks me about my high-school crush, I’ll have an enthusiastic answer ready to go. My mind will remember to immediately remember the positive, and to speak of this person with joy.

I have been on dates or flings with people from Brazil, Nepal, Sri Lanka, India, Turkey, Kuwait, the United States (including Puerto Rico, baby), and more. So many cool places.

Even though I didn’t get to know most of them super well, some of their life stories really stuck with me. A memory from his childhood would often tell me a lot about what it might be like to be this other person. It would expand my sense of the human experience.

I got to sleep over with an engineer once. I really liked that, because I missed math and always wondered how my life would have turned out if I’d just gone to school for something mathy. It is fun to feel like: I slept with my male-identified alter ego who became an engineer. 😄

Basically, every human on this planet gives you a lot to admire, appreciate, and learn from. Our mistakes and difficulties are beautiful too. This most certainly applies to people I met in a dating context. When I remember that, it’s easier to feel okay about myself, too.

Because when guys who once liked me look back on me, they could just as easily think to themselves, Why did I go out with that person? She was crazy, or self-centered, or not put together enough. But I hope that instead, they would think of me for the good they saw in me. This would make their dating history feel 1% like more of a good thing. It would probably help them better accept their own flaws too.

I will never be a “perfect date,” nor am I capable of shedding my clownish characteristics. But by looking back on anyone I’ve dated as if they were truly divine human beings, it gets so much easier to feel optimistic about the dates that lie ahead.

No matter what, I’ll continue to meet amazing sentient beings who are worth spending time with. I’ll continue to collect stories, interesting memories, and knowledge of the human experience. I’ll continue to learn and grow via good, worthy people—myself being one of them.

I hope this helps you figure out how to feel better about your unique dating life. You deserve to enjoy your memories, and to feel good about your growth curve in life and relationships. May your future be every bit as lovely and bright as you are.

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Photo: Volodymyr via Unsplash

Phoenix Huber
Phoenix Huber writes about personal growth, compassion for all, and daily vegan life. Based in Arizona, her hobbies include taking notes to remember her phone calls with friends, leaving effusive comments, and journaling. (She’ll get back to you once she finds some real hobbies that don’t involve writing.) An aspiring freelancer and researcher, Phoenix loves getting to amplify people’s messages of joy and kindness. Oh, and her family rocks! Find more articles from her on Medium, or donate to her via Ko-Fi and receive her eternal gratitude.


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