Lessons I’ve Learned from Dating – 2021 Edition.

So it’s been a little while since I’ve written here. Since my last post, I’ve gone through therapy, a pandemic, getting deported, having a hurricane hit where I’m staying, and was hospitalized due to COVID-19 for 3 days where I was hooked up to an oxygen tank after going blind & barely breathing for 10 minutes. Oh, and that was all in 2020. Can’t wait to see what 2021 has in store at this rate!

Based on that summary; you can imagine that I’ve had a thought or two about the world around me. I won’t try to cram it all into this post alone, so I’ll start with something that had a huge impact on me last year: dating. There was never an official title attached to either woman, but I spent almost 7 months seeing “I” and just over 2 months getting to know “L”. To protect their privacy, the context that I can share was that I’ve known “I” for almost 3 years and finally had asked her out at the end of 2019, and “L” I met off Tinder almost immediately after ending it with “I” at the end of May and we quickly would tally up 2-3 hour FaceTime calls multiple times per week, with eventually meeting in July. “I” and myself were going on dates (pre-COVID), and I spent almost all my quarantined time with her from March to May. Even though “L” was just over two months long, we got to know each other very well and I’ve had some of the most insightful conversations of my life with her, including the best first date I’ve ever been on. Looking back on my experience with both of these women (and other exes), I’ve come to realize a few key lessons about dating that I would love to share:

Date Who Is In Front Of You, Not Their Potential

This one wasn’t as obvious to me until last year… but who someone is today and who someone might be in the future are two very different individuals and only one of those people is actually real. All of us go through that honeymoon phase at the beginning of meeting someone new; it’s exciting, it keeps you on your toes, and nothing feels better than new love. The problem is, a lot of who this person is to you could be rooted in what you see in the future with them which is a false expectation as they may never actually realize that person.

“I” is a great individual. She’s achieved a lot already for being in her mid-20s. I saw (and see) a ton of opportunity for her to make an amazing life out of her business, and it was awesome to meet someone that I not only was physically attracted to but also respected before anything else. As someone who has had to do a lot on his own, I have a bias that made me grow attracted to her fairly quickly after learning about all that she does for herself. This is all great on paper, but as we all do, “I” has a few things going on in her life that she hasn’t figured out yet. With this still present in her life, she had told me multiple times over the span of us seeing each other that she wasn’t looking for a relationship and did not plan to commit to me anytime soon. I would hear her say these things, but I chose not to mentally process them as I was stuck on what kind of girlfriend she could be rather than the person in front of me. Looking back, I’m not sure why I expected something to change from her repeated affirmation of the relationship she didn’t want, but I can admit that it’s hard to overpower your emotions and think rationally in a situation like that.

Basically what I am trying to say is stop expecting other people to meet your expectations, because frankly, a lot of people will not. We shouldn’t expect someone to mold themselves or change just because we want them to, and vice-versa. On top of that, I never actually asked “I” what she thought of my expectations or told her about the image of her I had come up with in my head, so what else could happen other than eventual disappointment? Setting expectations only leads to let downs – so don’t do it. Again, it’s easy to type, but try to think about the individuals in your life and the image you have of them. How much of this is comprised of expectations of how they look/act/talk and how much is actually based in reality? To be honest, it wasn’t fair to her to do that in the first place as if I want to have a relationship with someone, that means being open about how I am feeling and what I am thinking and allowing that individual to provide their own input. Setting expectations for her to live up to is not her problem, it’s mine.

I can’t pretend to understand why certain things in her life are leading her to not want to date, but I should have respected that and not tried to force what I wanted. Being rational for a moment, I also know that anything forced usually doesn’t last long, so that shouldn’t be the foundation of a new relationship anyway.

Know Your Value & What You Bring

Flipping to the other side of this topic, it’s important to know your own value and what you can bring to the table before jumping into any relationship. At this point, I have a pretty good grasp on what I can offer my partner, and I try to communicate this early on, but the other person should know what they bring too and that always isn’t the case.

While getting to know “L”, we talked at length about our pasts which included finding out about an ex of 7 years that was still present in her life. As someone who still has an ex in my life (as a great friend I may add), I tried not to make negative assumptions about the role he may play in hers. Although from some of the stories I heard, it was hard not to feel like he was being manipulative and greedy while only running back to her to feed his emotional needs and not because he actually wanted any sort of productive future. I admit that I have a bias as someone who was pursuing her for romantic purposes and saw him as competition, but he didn’t seem like he was willing to work on any of the problems that they had together and I had very little respect for that.

Why did I provide any of that context into someone else’s dating history? Well… “L” is an incredible woman and deserves nothing other than to be treated like a queen, so it’s hard to see her treated less than that by anybody. Instead of writing out all the reasons this woman should be royalty… I’ll ask you to take my word for it and be content with a few listed here: She is smart, extremely honest and open about how she feels and what she’s thinking, plus knows exactly what she wants out of life. All of this was extremely sexy to me. That’s also why it was hard to hear her tell me on the phone back in September that she was giving it another shot with her ex and cut communication with me as a result. As someone who truly wants the best for her, there was nothing much for me to say other than to wish her luck and accept her decision. If someone tells you that they are pursuing happiness and it isn’t with you, it’s selfish to do anything except support that. That doesn’t mean it will be easy, or won’t suck though.

The hurt I experienced from us ending was different than the breakup with “I”. I don’t want to make assumptions of what “L” can and can’t bring to the table (aka Lesson #1 above), but I did recognize that value that she provided in my life and it was sad to think about it being gone. I never got to tell her how much I cherished some of our conversations, and respected how blunt she was, even if it meant opposing my view or calling me out. I probably need more of that in my life. Any potential of what we could be may not have lasted forever regardless of her ex coming back into the picture, but I definitely wish I had gotten to spend more time with her after recognizing how much of an impact she made on me.

If there’s anything that I learned from both of these relationships though… it’s that I have the ability to provide a lot of love and caring for someone who will be open to receiving it.

Be Truthful With Yourself: Why You Chose This Person And What You’re Looking For

The most important lesson that I’ve learned about dating isn’t necessarily a result of last year, but probably an accumulation of my entire dating life. I need to do a better job at being honest of why I am dating an individual, and what I’m exactly looking to get out of it.

Being blunt, I’ve jumped into a few relationships just because I think they will make me look better (on Instagram as well as in person). I’ve dated a few women due to their looks, or having a ton of followers on social which is all to fuel my ego about having a “trophy” wife as a standard of success. I’ve had this problem of trying to be better than all of the kids that bullied me growing up which has driven a lot of my decisions, but I’m now just realizing that these kids aren’t keeping tabs or give a shit what I am up to; so none of it matters. I need to be making decisions for me, and not because of what others may think or see. On top of that, only dating someone for their looks is extremely immature on my end as I’m objectifying someone which I have no right to do.

Although the honesty I am asking for from myself, and from you to yourself, is beyond the face value of someone’s looks. I’ve also dated people because I knew deep down that it wouldn’t work out and there is a part of me that feels like I don’t deserve to be loved. Going through therapy a year ago let me peel back some of the layers of bad dating decisions and I realized that I could admit that I knew some of my relationships were never going to work, yet I pursued them anyway. For reasons too long to explain right now, there’s always been a part of me that feels like I don’t deserve the life I work so hard to try and achieve, including giving & receiving love from a partner. Due to this insecurity, I’ve spent weeks/months with individuals that I will never get back just to fill the short term void of loneliness, but also knowing that it will eventually end and I’d be alone again. I think we all have this fallacy that there will be a ton of people that we meet, date and truly have a connection with… but I am starting to realize at 31 that it probably doesn’t occur as often as I hope. There isn’t this endless supply of people out there, and there certainly isn’t unlimited time, so we need to start valuing our time more if we really seek these powerful emotional connections. That starts with being honest about who we’re dating and why.

Don’t get me wrong, dating for fun or to hook up is completely fine, as long as that’s absolutely the only thing you want in that moment. If so – communicate it so that the other person can decide if that’s good with them or if they need to find someone else who aligns with their goals.