Lessons from My Dating Past to Present

two paths.jpg

My dating career isn’t too extensive, though its trajectory does seem to show some promise. By that I mean I haven’t dated too much but I feel like I’m getting better and better at reading and picking out good guys, and even men.

My first adult relationship happened at 25 years old. The four years prior to that were spent infatuated with the idea of a relationship with this one dude. Said dude is now happily married. As you can gather from just that, I wasn’t the brightest when it came to affairs involving the other sex.

Maybe it’s because my baseline of knowledge and wisdom isn’t that high to begin with, but I feel I’ve become less and less clueless with every guy I’ve dated. I haven’t necessarily dated for long periods, the longest is 9 months, and not all were official, but I still consider them significant in my dating history haha. I’ve categorized the lessons by whether I’ve learned to become a better person as an individual and a better participant in a relationship.

It’s a little unnerving to think that the guys I’ve dated might be reading this but really, I have nothing bad to say.


The First

  • Personal Lesson: If you don’t ask, the answer is always no.

He’s a sales guy so that’s what he does all day — ask questions to get what he wants/needs. I don’t feel comfortable asking questions to probe or just to find out more information and options, even if it could yield desirable results such as getting compensation for a cancelled flight or freebies at a store. As such, I typically don’t ask questions I think are imposing or imply I want something. I think I pass by opportunities everyday because of my timidity. This has stuck to me and slowly, I’ve learned the business of life, that truly, if I want something and it’s worth the interaction, make it known. It doesn’t have to be rude or demanding. It just has to be honest and clear.

  • Relationship Lesson: Know my boundaries.

The First is always hard, isn’t it? There’s no precedence, no guidance, no experience to use as a benchmark. I pretty much gave and gave and gave thinking that was the best way to love. And ended up with nothing lol. I actually ended up way broken and cried for two weeks straight. I laugh about it now but those was some hard times, I tell ya. After those two weeks, I realized loving someone isn’t about them getting what they want. It’s about loving and knowing myself and being someone that can relate to the other. It’s impossible to relate to another without understanding yourself — otherwise, how else will you know what you want, what you feel, know, etc? If they like the way I relate, then we do the relationship. If they don’t, we move on.

The Second

  • Personal Lesson: Friends are your living breathing resumes.

Through this guy, I learned how important it was to have legit friends. When we dated, about 70% of the time I spent with him was also with his friends. There were moments when he was away, getting a drink or in the restroom, and I would talk with his friends. They always vouched for him, talking about their friendships, his character, and personality in a non-salesy way haha. A huge part of the reason I respected him was because his friends respected him. Obviously that can’t be the only source of respect but til the very end, I was pretty impressed not only with his relationship with his friends, but the fact they were good people. It indirectly let me know this guy was good people too. It made me appreciate my homegirls even more since I’m proud to be their homeslice and vice versa. They are my accountability — should anything happen to me, you can go to them to ask anything about me. I can leave them alone with anyone and know I’m taken care of. And I would do the same for them.

  • Relationship Lesson: Don’t be afraid to ask the hard questions.

This is sort of similar to the Personal Lesson taught by the First one, but in the realm of relationships and dating. I learned that I can either sit around guessing and wondering what is going on on the other side of the relationship. Or, I can throw the whole coy female act out the window — which I suck at anyway — and get my answers. Call it impatience, brashness, unladylike — I don’t mind. I don’t hate a lot but if there’s one thing that comes close, it’s wasting time, and especially wasting time to put up a front or adhere to social norms. No thanks. If it’s not the relationship for me, it’s not the relationship for him and vice versa.

The Third

  • Personal Lesson: Inaction is decision.

Bam. In yo face. This convicted me quite a bit. Actually he got this from his brother so half a kudos to his brother and the other half to him for sharing. Over the past year, I’ve picked up on this more and learned to exercise this. I’ve spent a lot of my life in this limbo, the swaying, the shaky top of the chain-link fence prolonging and perpetuating my fears. It’s not a great place to be. Because we’re living creatures, hungry by nature for action, movement, the more. Inaction breeds doubt; doubt breeds fog; and fog breeds nothing good. Through this, I realized no matter what, a decision is being made. Today and forever, I want to live by design, not default. If there’s fear involved, I still choose make a decision. Once I jump, at least I can land somewhere and go from there.

  • Relationship Lesson: Don’t fall in love with or settle for the potential.

There were so many right things about this guy — ambition, generosity, patience, ability to cook, healthy relationship with family, and the list goes on. But there was still something I didn’t quite see while we were dating. I felt — no, knew there was potential, and that kept me going for a bit but after a while, I couldn’t. Once I had evaluated that he was lacking this thing, I couldn’t see past that (which I consider my flaw), and everything he did from thereon out was assessed based on that judgment. It wasn’t fair to me and to him, especially, since I was interested in what could be, rather than what was, as imperfect as it was. That’s just unsatisfying and cruel.

The Now

  • Personal Lesson: Pay attention to the little things.

This guy like to cook. Correction. He loves to cook. It’s evident in the way he seasons the meat, vegetables. It’s evident in his knowledge of sous vide. It’s evident in the way he knows the fundamentals, which give him the arsenal to fix just about any mistake. It’s evident in the way he gets lost in it. It’s evident in his concentration as I view from the sidelines, typing away on my laptop, writing and working. It made me ask the question, what do I do with that much passion, attention, and interest? What gets me going? For me, that’s writing and connecting with people. Seeing another person immersed reminds me what it looks like and means to be lost in art and heart. And that reminds me to pay attention to what that looks like for me.

  • Relationship Lesson: It’s okay to not be joined at the hip.

I consider myself pretty independent. I like doing things alone. I like doing things on my own terms. Maybe that makes me cold, unapproachable. Maybe that makes a horrible girlfriend. I used to think the start of a relationship meant the demise of independence and self (see Relationship Lesson taught by First). Not true. I am a whole person and I choose to believe the other is as well. I will treat him as such and know that I am okay doing my thing. And he has been awesome about it, constantly reassuring me that he’s cool with it. I feel supported not just as a participant in the relationship but as a person. I’m very appreciative. Because at one point, butterflies fly away, heart rates slow down, chocolate gets digested, flowers become crunchy… and what’s left? Yourself and the other — partners and individuals. I think if we can let the individual part thrive, the partner part will flourish.


I 100% believe I’ve become a better person through my experiences with these dudes. I hope they can say the same about me. If you’re reading this and identify yourself as one of the guys up there — thank you.



, , ,




2 responses to “Lessons from My Dating Past to Present”

  1. amyksu Avatar


    1. Grace J. Kim Avatar

      Hahah thanks girlllll!! I think your dating history would have a lot to say too… I’d be curious to read!! Just saying hahah

I wanna know what you think

%d bloggers like this: