As some of you know, I’m in the midst of a 3-week Pacific Northwest expedition (2-week solo road trip followed by a 1-week Alaskan cruise with my family). The day it started I posted the blog, “Digital Dilemma” which discusses a few ways in which the modern digital age has shifted our priorities and values as of late. It’s a critical opinion piece that received some great feedback from readers.

With that being said, being solo on the road creates A TON of opportunity to get lost in my own thoughts and experience a range of emotions. I’m sure you can relate too. These waves of feelings especially hit me when I start thinking about-

Past vs. Present vs. Future
Existential vs. Essential
Little Things vs. Big Things
Who I Was vs. Who I Am vs. Who I Want To Become
The People Who Influenced My Life

For brevity’s sake and what has come to mind recently, I’m going to focus on the last one: The People Who Influenced My Life.

Particularly, All of the Women I’ve Loved Before.

I think its lame that men don’t talk as freely about these things. I get it, our brains and emotions are wired a bit differently than women. A lot of guys tend to go with the default responses of, “Yeah she was a little crazy” or “Things just didn’t work out”. While both of those qualities may be true, I think a lot of us struggle to appreciate, or simply avoid appreciating, just how much the culmination of meaningful women impacts us over the course of our lives. Particularly the women we loved.

Love is a subjective concept. And like most people, I’ve put a lot of thought into what it means to me recently. What love was for me 5, 10, or 15 years ago is certainly not the same as what love is for me now. I’m confident in guessing that you, too, are just the same. And much like me, you probably also thought you were in love with someone in your past only to realize later on that you weren’t. Or, the absolute reverse.

The reason for that is pretty simple. During those various points in our lives, we were different people than we are now.

We mature, we learn more about the world, and we expand our horizons through travel, friendships, heartache, challenges, disappointment, and surprises. What excites us and what we value in High School vs. College vs. Young Adulthood vs. Middle Age is guaranteed to evolve. Shit, what moves us Last Year vs. This Year is already different enough.

So that brings me to the point of this blog-

I’m extremely lucky in that I never experienced any ill will or had a nasty breakup with any of the women I’ve loved before. Maybe it’s them, maybe it’s me, or maybe it was the two of us together. What I do know is that I only view them as great people who had positive influences on my life and helped me grow to become a better person.

And for that, I want to thank them while sharing my anecdotes with you. Maybe you can relate to one of them a bit, or simply appreciate the simplicity of this blog. I think you’ll also notice the maturity increasing as you keep reading, as our love lives typically do. Either way, you’ll learn just a little bit more about me, and I’m okay with that. Writing has become my new therapy.

To keep them confidential I’ll use initials, even though I won’t embarrass them or write anything personal that crosses the line. None of them had any previous clue that I wrote this. Hell, they may not even agree with my perspective. For those who really know me, you’ll be able to easily determine at least one, if not all of these women.

There are 4 of them.

MA – First Love

I was 16 years old, starting my junior year of high school. I just transferred to a private Catholic school after attending public schools my entire life. My Mother recently dealt with her second divorce, and thankfully she qualified for tuition assistance and the schooling was paid for otherwise I would have never completed my final 2 years of high school there. And I certainly would not have crossed paths with my first love.

I met MA at one of the first football games of the year. 5’10”, brunette, athletically built, and my God was she well-developed for her age. During the game, she went to smoke a cigarette away from the crowd and that’s when I noticed her and we started chatting. She had a sarcastic sense of humor and a bit of an edge. She also seemed like the type who kept to herself and did her own thing, which definitely intrigued me. We exchanged phone numbers, and I believe it was the next night that I talked to her on the landline (which I stretched outside to the back porch to prevent waking up my Mother) for about 4 hours until the wee hours of the morning.

We did all of the things that most high school couples did together – talked on the phone, went to the movies, attended house parties, got drunk or high, snuck out of the house at night, and skipped classes. We also lost our virginity to each other. As you would expect, neither of us had any fucking clue what we were doing at the time. The whole thing was awkward, we were both nervous, and my first attempt at using a condom was a complete and utter disaster. Over time we got better at it, but it would certainly pale in comparison to what either of us has become accustomed to now.

We were young. Naïve. Stupid. Innocent. Inexperienced. But we did it all together, and leaned on each other when the time came.

Her home life was tough and her schedule was strict. On top of it all, her father was overbearing and abusive back then, amongst other things.

She was exceptionally good at tennis, and was constantly busy with practice, traveling, and tournaments. Her frequent time away never really seemed to bother me, as I simply looked forward to the times we could spend together. She eventually went on to be ranked nationally and attended college on an athletic scholarship. She was that fucking good. I remember that I used to dream about her becoming a pro tennis star, and I would be content as the cool, ambiguous boyfriend watching from the stands. Clearly that didn’t pan out as dreamt.

I dated her for 2.5 years, but like most high school sweethearts our connection fizzled out over the course of our freshmen years in college. She went to school in DC and me in Chapel Hill. Sadly, she had an extremely unfortunate ending to her first year, one that I cannot publicly discuss. That occurrence combined with the new stimulation of college changed things for us. I ultimately had to let go, pivot, and immerse myself in the seedling phase of young adulthood.

MA was my first love. For that, I will be forever grateful. She showed me what it all meant. Our relationship taught me at a young age how to care for someone who is going through hardships. I also give her credit for never really judging me back then, while staying true to herself. This is extremely rare for someone in high school. Those are two attributes that I carry today, and that I have valued in a significant other ever since.

Thank you.

KU – Tentative Love

By the start of my sophomore year of college I was finally comfortable being away from home. My freshman year I visited home an average of about 1 weekend per month. Toward the end of my first year, however, I established some go-to college friends, tried harder in classes, had a few more sexual encounters, was moving on from MA, and fully embraced life as a Tar Heel.

I was such a weird fucking kid at that point in my life. I shaved a zig-zag style beard on my face, I wore socks with slip-ons everywhere I went, and I generally rocked an undershirt as my apparel of choice with a visor. Jesus Christ. WTF?!?

Anyways, my best friend in college, Zack, had a pregame gathering in his dorm room at some point in the Fall and mentioned that he met a couple girls that would be joining. Booze. Girls. 19. Got it.

And that’s when KU and I connected. She was a freshman. 5’5”, light brown hair, intelligent, witty, cute, southern belle. She managed to pull off being shy and bold at the same time, and was persistent in maintaining my focus and attention over the next few days. After describing my appearance back then, she could have only been attracted to my level of not giving a fuck.

If I remember correctly, our first follow-up dinner date was at Bandido’s – a true gem of a college Mexican restaurant. The walls and ceiling were covered with photos of people who managed to finish a gigantic burrito in a short amount of time. And for some reason I recall that she wore a plaid, button-up style shirt on that date. It’s weird the small details you can remember sometimes.

We clicked instantly. Her smart, sassy demeanor worked well with my clever bullshit. And as broke college kids who lived within walking distance, we spent a lot of time together that school year. We were on our own and we were away from home. It was us navigating the weirdness of college life with one another – half caring and half getting fucked up, dealing with the uncertainties and questions that rested in the back of our minds about who we would ever become as people. Let alone, who we even were then.

I always admired her work ethic. I was never the student that gave it 100%. I half-assed my way to getting A’s my entire life. She studied very hard to maintain outstanding grades which eventually led to her becoming a Speech-Language Pathologist. She knew exactly what she wanted to do professionally and she was very dedicated to it. That’s a very uncommon thing for most people at that age. A part of me envied her then, as I was still navigating many different interests and didn’t have such a clear-cut path in mind for myself.

I dated her for about 2 years in total. We were on and off and wanted to see other people for months at a time, so it wasn’t entirely continuous. It’s college. It’s common. You’re still half-kid, half-young adult. Likewise, you still don’t know much about the real world at that point.

Once my senior year approached, we hooked up a few more times but we knew our fun chapter together was trickling down to a slow drip. It was time to brace ourselves for what was next in life, not to mention she had more schooling ahead of her. Nevertheless, we managed to stay in touch and remained in contact until she finished her undergrad a year after me. The Tar Heels won the championship that year, and we watched the game in Chapel Hill together with friends.

KU taught me to not squander my time with a significant other, because I did at moments with her. Even when there are obvious excuses, question marks, or hurdles in front of me, I should be upfront with my intentions and expectations with a romantic partner. That has translated for me later on in my relationships, by being more upfront in the early stages. This pays dividends in the long-run when I want to maintain accountability for my partner or myself.

Thank you.

SP – Tumultuous Love

The first couple of years living in DC I was simply adjusting, and trying to enjoy young adulthood in the city. I dated a couple of girls during this time, but nothing truly substantial. I was focused on working, paying off debt, making ends meet, having fun with friends, and beginning my MBA.

And then the phone call came from my distraught Uncle.

My Dad unexpectedly passed away. It was October 30th, 2010. I was only 24 years old, still 3 months from my 25th birthday. The broke, lost, young guy I already was…now added dismantled and directionless to his list of attributes. And yet I still continued on, pretending as though everything was okay without going through the necessary stages of grief (denial, anger, bargaining, depression, and acceptance). I wanted nothing more than to sweep it under a rug and forget about it. Unfortunately that type of dirt never disappears until you deal with it.

I met SP while I was going through this phase of my life. She was less than a year younger than me. 5’3”, dark brown hair, Greek, dynamic personality, and a dancer’s figure. She was full of jokes, designer bags/clothes, a shitload of energy, and smoked weed on a daily basis while teaching special-ed, elementary students. Pretty confounding I would say. But her charisma definitely captivated me.

After we had sex she straight-up told me, “I better hear from you again.”

And so that was that. I always appreciate a bold gesture. I followed-up.

Already in a vulnerable period of my life, I was willing to see where things would lead. She still lived with her parents at the time and came from a stereotypical Greek family- loud as hell, always tons of food around, and parents that likely sheltered and stunted her independence and personal growth the first couple years out of college. She too, was lost in her mid-20s. And maybe that commonality is what subconsciously drew us together.

Nevertheless, we found ourselves going full-steam ahead. Five months into our relationship, we embarked on our first international trip with a significant other. Italy and Croatia. 17 days. In hindsight, this is when the cracks were first exposed. At some point in the trip, she brought up arbitrary timelines of when she envisioned herself getting married and subsequently having kids. And that if her and I were to work out long-term, what her general expectation would be.

As an Aquarius who doesn’t like such rigid confines (especially at that age), this made me uncomfortable. We got into an argument about it during that vacation. Much like we did with virtually all of our arguments, we haphazardly came to a conclusion and then sought out the next adventure or time to spend together to forget about it. However, during the last several months of our relationship those arguments became louder, more frequent, more draining, and less resolved.

Don’t get me wrong, we shared some of the most amazing times of my life together. We went on another international trip together to France, Spain, Monaco, and Portugal. Over time, she bonded with my Mom (and stays in touch with her to this day) and I bonded with her parents. She immersed herself into my group of friends, while I found appreciation for a couple of hers. All in all, we felt deeply for each other and were carelessly in love. The highs were high, and yes there were more of them….but the low moments and discrepancies were unavoidable.

I dated her for 2 years. Unfortunately I was hiding from depression, and she had trust issues and relied on co-dependency. It was not going to work long-term and as emotional as it may have been for us, we knew that neither of us was ultimately in the right place or time in our lives for us to be successful together.

SP taught me that you have to be okay with yourself, on your own, before you choose to include someone else in your life (this may be the most common mistake people make). She challenged me many times to open up more, to share my feelings, and to express myself better. She showed me that the best moments in life should be shared with someone else and that you should always continue exploring things with a significant other no matter what. Most importantly, she reiterated to me that I needed to reach out and be the proactive one in trying to rekindle a relationship with my brother. Something that was long overdue.

Thank you.

MT – Free-Spirited Love

Wow, how much different my life was by the end of 2013. I was getting close to finishing a year of individual therapy, as well as group therapy to deal with deep –rooted issues and learn about myself. I also completed my MBA, grew an amazing networking group of event professionals called Metro Event Specialists, and spun my event planning business, Troyal Events, off of those connections. Oh yeah, and I also bought my rowhome in DC!

Needless to say, it was the best I felt in a long time. The positive momentum was certainly on my side. It’s amazing how the way you frame things in your mind can dictate how it makes you feel and ultimately respond. I was confident, and I was alive.

I soaked it all in until the summer of 2014, and that’s when I met MT. A little less than a year older than me. 5’2”, dark brunette w/ a purple streak, exotic and pretty, mixed-Filipino, tatted up, and west coast chill. You wanna talk about a contagious free spirit? Yep, this was definitely her. A bit more shy and introverted compared to the others, but she was always smiling and without a doubt the sweetest girl in the room and very generous. The positivity radiated from her, and that meshed perfectly with my status at the time.

Based on my last relationship, I knew that I needed to ease into this one and go more with the flow. Plus, she was a bit of a flake at first. It was hard to pin her down.

At one point I gave her the ultimatum, “That’s 2 times in a row you’ve cancelled. 1 more time and the chase is over for me.”

It took us about 6 months to get to the point of being exclusive.

She was a late bloomer as far as academics were concerned. When we started dating, I motivated her to return to school to get her degree. Albeit at her own space, she followed through on it (and will actually be graduating in a month! It’s impressive to do that starting at age 30 to improve the course of your life).

She was super close with her family, and a massive family at that. Her Mom’s side was a stereotypical Filipino family that engaged in frequent get-togethers, massive birthday celebrations, a million cousins visiting, and so much damn food and gifts. She had two siblings, both married, and both with children. To put it simply, her social life primarily consisted of her family as there was no shortage.

This was much different for me. My family was more fractured and condensed down from what it once was. I visit my Mother a few times a year, my brother 1 or 2 times a year, and my Uncle and Aunt 1 or 2 times a year. For me, my friends made up the remainder of my family. It’s been that way for most of my life. Nonetheless, I enjoyed spending time with hers over the holidays or special occasions which even included her Brother’s wedding. Her Mother, Brother, Sister, Cousin, and I bonded pretty well whenever we saw each other. And she certainly connected with my Mom (who she also stays in touch with to this day). We went on multiple trips, weekend getaways, and vacations together, and I took her to Iceland over New Years. In general, things appeared to be on autopilot for a while.

And that’s where the mistakes began.

I became extremely busy with Troyal Events, and my weekends were getting fully booked. On top of it all, I invested in 2 restaurants around the same time which soaked a lot of my energy being at them regularly during the first year of opening. Not to mention I have sociable friends who are out and about a lot that I enjoyed spending time with. Likewise, she was working full-time, going to night classes, and lived out in Rockville. We simply didn’t spend enough time together nor communicate as regularly as we should have about how it was impacting us until it ran its course. Personally, I needed to slow down the pace of my life.

Regardless, I had some of the greatest moments of my life with her. My friends all enjoyed her, my Mom adored her, and I expressed my feelings and concerns with her more openly than I ever did before with a significant other. I felt a sense of calm almost every time I was around her. It was as though we connected at a spiritual level. I considered her the Yin to my Yang as I was more of the go-go-go “push”, and she was more of the go-with-the-flow “pull”. I can admit that I occasionally had visions of marrying her. For the first time in my life those thoughts actually crossed my mind, however fleeting they may have been. I think it was my mind’s way of telling me that I had progressively grown better at choosing a better complement.

However it seemed like each time we saw each other needed to be significant because it wasn’t as frequent as either of us ever expected. Over time, she gradually became unhappy and I slowly grew distant. Many things she harbored for a long time, several months even, before she made me aware. Conversely, my heart simply wasn’t 100% in it anymore. It was as though we were walking up 2 separate hills and neither of us stopped to ask for directions.

I dated her for 2.5 years. It was one of the hardest choices I had to make to end our relationship. I eventually came to terms with the fact that I had grown distant and lost my belief that we were ultimately right for each other. It’s certainly not easy to let a significant other go – particularly the older you get. When you’re in your 30s, the gravity of relationships seems to have more weight. The expectations, level of sacrifice, and societal pressures are all seemingly heightened. In the end, it took a lot out of me to break someone’s heart knowing that it was the best for both of us.

MT taught me that I needed to slow down and simplify my life, so that I would appreciate the things right in front of me. I’ve made concerted efforts to do that ever since. She showed me how important it is to connect with my family, or at least make an attempt to. While we dated, I saw my brother more times than I did the previous 7 years combined. Her example rubbed off on me. I learned that I could go through a relationship without having to yell whenever there was a disagreement. That you should always try to process things in a mature fashion. She also caused me to be ever-so-much warmer around people, and to smooth the edges a bit. Essentially, she taught me how to be selfless toward someone that you love…because she was certainly that.

Thank you.


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