Love, dating and relationships

Tree Trunks & Mr. Pig from Adventure Time

Two years together

Recently it was a special day, because it's been two years since I met the love of my life. She's pretty special and I feel quite lucky to have found her. Sadly you, the Internet, probably won't meet her unless you know me personally, which is unfortunate cause she's great.

Hopefully though, you'll still find this reflection useful anyway, because I'd like to talk more about my experiences dating in general as well as how we've maintained our relationship up until now.

Disclaimer: I'm not an expert. These are just my reflections. Your mileage may vary, especially if you're a person of color, queer or someone that isn't a straight white male. If you're lacking stability in your life, it can be harder to hold any kind of relationship at all.

That said, I offer you my ramblings.

Table of Contents


A long and bumpy road

I didn't start out confident about who I am. I slowly discovered who I was as I became an adult. These days I'm kinda glad that I was too nerdy and awkward in high school to date anyway. It saved a lot of drama and heartache during some crucial developmental years, but at the time I was worried about finding someone and you know, doin' it or whatever.

My pick-up phase

I've always been independent and curious to learn, so one day in high school I decided to read more about dating online. When I came across the pick-up community on Reddit I spent a lot of time reading advice and other stuff. To be clear, it's a bit weird. There's some hit-or-miss advice and some questionable views on women. The ideology around pick-up can get toxic if you're not careful to read between the lines, but the advice offers a concrete view of the process to someone who is absolutely clueless.

There were a few gems that stuck with me to this day. In fact, the best advice you could even apply to other types relationships and stuff in general.

Advice like:

  • Leave someone better than you found them.
  • Take care of your physical health.
  • Dress in clothes that fit. In my case I altered them.
  • Don't be afraid to make advances.
  • Rejection is good because you waste less time wondering.
  • Learn how to build rapport.
  • Self-improvement is sexy: Go to the gym, pick up a hobby, etc.
  • Do things that make you happy and own it (as in, don't be ashamed).

There's probably more, but this is what stuck with me as some of the healthier gems of the pick-up community. Some of the toxic things to avoid can be basically be summed up with: avoid any advice that emphasizes quantity over quality. When you start to focus on more hook-ups over enjoying yourself with someone then you start to walk down a path which overemphasizes sex as a goal instead one of many ways to build a meaningful connection with someone.

Don't get me wrong, sex is fun (important to remember that sometimes it's not though), but when you start to care too much about it then the desperation reeks from miles away. That impacts your ability to have fun too which creates a dangerous spiral of Bad Vibes.

As you can imagine, at first I spent a lot more time reading than I actually did talking to women. I did try to apply what I was learning online in the real world, but quite frankly I was just too damn shy and nervous most of the time.

I also had unrealistic expectations. I would overthink situations as simple as walking by a cute woman on my way to class in college. I would kick myself for not immediately stopping in the middle of the sidewalk (bustling with people) to tell them they're cute and ask them out. The reality is though that most people don't want to be hassled when they're on their way to something that's time sensitive like classes, so I probably saved myself some embarassment.

That's not to say asking out someone you've never met (called a "cold approach" in the lingo) can't work, and you should definitely get out of your comfort zone at some point (in a way that respects people's rejection if it happens), but I placed some heavy pressure on myself because dudes online made it look so easy by editing together footage of the times they were actually succesful.

A lot of my obsession came from the fact that I just really wanted to know what it was like to be in a relationship and have sex, because it's glorified to no end. I mean for good reason, being in love with someone is great.

But it's also important to understand that some relationships are horrible messes that you'd be much happier not having. Like really, really fucking bad. Luckily I've never had a truly toxic relationship, but I'm sure people out there will tell you that love doesn't exist because they went through some fucked up shit that ruined them forever.

Actually talking to people

What helped me more than any advice a man could write up about seducing women was just becoming friends with women. In my attempts at talking to women I was interested in I made a few friends who I never did anything romantic with because they weren't interested in me or they weren't in a good spot to have a relationship.

As I got to know them I found they were cool people. In fact, I found out I just plain like women in general and hanging out with them. They're like, actual people who have personalities and stuff, it's weird I know!

However, I will say that it's important to mention your interest in someone from the get go instead of letting things build up and expecting it to "just happen", because if you don't then it becomes awkward the longer your let your feelings grow unmentioned. Remember, being rejected isn't a bad thing and who knows, maybe they feel the same way! Make a move, see where things go. Being friends can be fine too, just don't expect they'll change their minds if they said they're not interested at all. I've learned that the hard way.

There were very few times where I did anything that could be considered a cold approach, and even fewer that were successful. Not to say that it can't be, but you really have to build your social-emotional skills to read people and your ability have meaningful conversations with strangers which will likely come with a lot of painful failures before you get there. In fact, it's a good life skill to build for meeting people in general, but it takes work.

That said, far and away the easiest times I had in hitting it off with people were in social settings with friends of friends or at a party. It eases a lot of the tension when you're in a safe place having fun with people you already trust. Parties are a great place to meet people, but you can also just meet people through hobbies, at a café, or out and about with friends. Don't ask people out in a dark alley or the cashier at the grocery store! It's weird and will make someone feel threatened if they reject you.

I don't mean to say that I don't get nervous talking to people either, cause I still do, but it's easier to get over it now. Because the single thing getting in the way of actually doing it, is just doing it. It really depends on how I feel mentally though and my interest in actually socializing. In the end it's something that takes practice like any other skill though.

Most people are clueless when it comes to relationships and meeting people, so you shouldn't feel bad if you also are. Be honest about it and the other person will appreciate that more than painful attempts at powering through a macho facade. If they don't, fuck 'em (well, not literally).

Making moves

One of the areas I struggled with the most when initially starting out was how to make a move. What the hell does that even mean, you know?

Really, it's not as straight forward as it seems. Making a move can look different depending which stage of getting to know someone you're at. Saying "Hi" is a great first move, but whatever you do don't use a pick-up line. It's about as interesting as saying "SO HOW BOUT THAT WEATHER!?". Well, unless you have some damn good delivery, but if that's the case you don't need my help anyway.

Everyone has their own style too. I would often say hi, compliment/comment on the thing about them that drew me to them in the first place (a nice shirt, their hair, or maybe they've got a cool button on their backpack). From there I would try to ask a question that would tell me more about them.

My go to get-to-know-you question in a lot of social situations these days (beyond dating even) is "What's the coolest thing I should know about you?", because it does a few things. First, it tells you if they're actually interested in talking to you, because if they're not they'll just say "uhhhh I don't know", which even if they ARE interested in talking to you is already a bad sign.

Secondly, it gives you an idea of what they're into and starts a conversation that's actually interesting instead of what job they sell their lives away at or some other mundane bullshit that nobody cares about but everyone asks because we're so deprived of excitement in our lives that sometimes don't remember what fun is... Ahem, anyway.

The key isn't that it has to actually be something cool, it's just an open-ended question that can lead to a genuine conversation. Come up with a question about something that interests you.

When you're making moves the key is to figure out:

  1. Who they are.
  2. How receptive they are.
  3. If they're worth your time.

You make yourself vulnerable by putting yourself out there and facing the potential for rejection at the hands of the other person. How they respond to that tells you if they're a person worth talking to, or equally as important, if you need to readjust your style and approach.

Always respect rejection! It doesn't mean you can't try again later, because sometimes people just need to get to know you better before they're willing to open up in that way. The same goes for advancing into sexually charged territory. A friendly touch on the arm after you've established a base level of trust, telling them you think they're cute or asking them what they'd do if you kiss them are all ways to call the question of "are you into me?" and escalate things.

Never force yourself onto someone though. Yes, confidence and assertiveness can be sexy, but so is respect and consent.

There are whole books written on the details of making moves, but really you should develop your own style that flows with who you are. You're not a caveman trying to hunt a gazelle though, you're trying to get to know someone enough to have a good time.

As for the timeline on these things, there really isn't one. You can go from "Hi!" to sex in a day (or less) or it can drag out over a few weeks or a couple months (likely not much longer though before they start to wonder if you're even interested). It really depends on how trustworthy you come off and the person's past experience with relationships. Some people have been hurt before so they may be reluctant to open up.

Suffice to say it, eventually I figured dating out.


My first girlfriend

I finally met someone who wanted to keep seeing me more than once! I had technically dated people prior, but not successfully. We met through mutual friends, but didn't hang out right away. However, I eventually came back a semester later after winter break with freshly altered clothes, my hair held together with cream so I didn't look like a middle schooler and new found confidence.

Things didn't start from 0 to 100 in one swoop, instead it was gradual. We both were interested in other people more than each other initially, but as we got to know each other we found out that we really liked each other. Eventually we started hanging out more, going on adventures and decided to do the whole boyfriend/girlfriend thing.

It was nice to finally be with someone because I could stop worrying about dating. I learned more about what I was actually looking for in a partner, which helps you avoid falling into the trap of just being in a relationship to avoid being alone. Being alone is ok, or at least it's better than being with someone shitty.

But things didn't last forever, which is common for college relationships anyway.

My first breakup

When I came home from a long car ride only to get dumped in a truck outside the dorms, it definitely wasn't a great feeling. But the most important thing she told me was more or less "It might not seem like it now, but things will be better eventually". It didn't feel great, but it never does for either side.

Eventually things did get better though and we were better off individually for it.

To help ease the pain I hung out with friends. It was super important to be with people who I could just exist around. It was part of the healing process as I felt and dealt with my feelings. It was good to lift my spirits. Not all breakups are made the same of course, but if it's unwanted then it's rough.

Hobbies helped me maintain composure too. Music is always one way I've gotten through stuff, this was no exception. Getting outside helped a lot too. I spent some moody evenings in the marsh by the cemetary, I'll admit it! Finding solitude when you live at the dorms is hard, so being outside helped.

Later I learned that sometimes it's better to break up than to carry on with a relationship that just won't work though. Sometimes there's just a fundamental difference, changed feelings or some reason breaking up makes more sense. Sometimes it's mutual. You should try to communicate if you want to save the relationship, because talking it out can help, but you're not obligated to either.

It's not really easy no matter which way you shake it, but it can be healthier to acknowledge it won't work if you reach your tipping point and decide it's been enough.

Finding the right one

Since then I dated around and found who I'm with now. It's been better than I could have hoped. A lot of luck was involved in meeting each other, but staying together has been a commitment that requires work. Not an excessive amount, but sometimes it requires thought and effort. For me past experiences helped so I was aware of the pitfalls and problems that can come up.

I realize to some people that two years is nothing, but to me it's the longest relationship I've had, so that's what I'm working with lol. I foresee many more :)

We met online through OKCupid, which filtered out a lot of fundamental questions that can take a while to come up in a relationship the old-fashioned way. So out the gate we were pretty well matched. It was nice.

Some things can't be worked on. But for those that can, I've identified a few important areas that at least merit mention.

TIPs on Trust, Intimacy and Passion

There's a lot of cliché remarks about the importance of communication and commitment when it comes to dating, but that's because it's true. They're an important tool to help maintain these three areas of a relationship, otherwise they can start to degrade over time. When trust is lost, it closes off intimacy which will start to eat into the passion that brought you together in the first place.

Everyone has different ways of expressing their needs. Some are quieter because they've been socialized not to complain and others will let you know when you're fuckin' up no problem. Sometimes we aren't even in tune with the ways we're reacting to a situation ourselves until it's been going on for a while. Espcially if you don't reflect much and find your life is a blur that you can barely keep track of.

Regardless of how you do though, it's important to be able to express yourself in a healthy way with a partner who is willing to listen. Inevitably, something will happen that you or they didn't mean to fuck up your trust of each other, whether it's hurt feelings, a misunderstanding or you-name-it. At some point, we just fuck up because we're human.


Trust is when you're willing to to make yourself vulnerable to someone in some capacity.

That means you expect that what they say is true, they'll follow through on commitments and you can depend on them in general. If you don't have that, then it's not a healthy relationship. That isn't to say you should blindly trust people, because it should be earned. But if it's not there then that's bad.

When that trust is broken so is the special connection that makes the relationship work. Even in friendships trust is important. Without trust, waiting for a text message can lead to paranoia that your partner is cheating. With it, you know that whatever they're doing is fine and you'll see them again at some point anyway.

Many things can eat away at trust, so it's important to identify the root cause of the problem which requires communication and commitment to a solution that takes dealing with difficult emotions sometimes.


Intimacy is a space opened up through trust. It's when you share your existence together as you are without bullshit in between and accept each other openly. It's brushing your teeth together, eating dinner, watching movies, goofin' around, playing games and sharing your personal stories.

If you can't repair trust, you can't repair intimacy. Sometimes it's them, sometimes it's you, and sometimes it's a situation that can be worked on. But without the ability to trust one another, opening yourself up is hard.

Intimacy provides the spark that reminds you why the person you're with is special. It gives you a connection that only you and the other person share which seperates them from just any ol' body. The special appreciation that intimacy gives you for someone is what fuels passion.


Maintaining a relationship isn't just about fixing fuck ups. It's also about excitement and fun. Passion comes from being with someone who makes you feel great.

Yes, that can be as sexual as it sounds (it's an important question for compatibility at least), but it goes beyond it too. Making someone feel appreciated, having a great time goofing around, playing video games, going out to dinner, showering in the morning, doing new things and just living life in general with each other in a way that makes you feel glad to know the other person.

Passion comes from genuinely liking the person you're with and expressing it in the space opened up by intimacy and trust. Finding time to keep it alive is hard. Sometimes it means doing things you might not always like. Cleaning around the house, taking care of yourself and otherwise just being an Adult Human Being are important ways to maintain the fabric of a healthy relationship and the environment it lives in.

Because if your partner has to take care of two people all by themselves, they're gonna burn out quick.

Dating and Relationships: Solved!

So this post turned out to be waaaaaaaay longer than I had anticipated and there's still things I feel like I haven't covered yet. If you've stuck around, then hopefully you found this useful. This is just my own experience. Dating and relationships are complicated subjects that a lot of people are interested in. It was something that came up in my poll of interests y'all had!

My goal was to offer some insights that I feel are healthy and generalizable for those curious. I know that if I was younger I would have found these thoughts useful to myself trying to navigate what it means to date, have relationships and all that stuff. For young men growing up, there's a bunch of semi-decent advice wrapped up in unhealthy views of sex and women that focuses on the result and not the process or even meaningful connection. I'm sure the same is true for women and folks who live beyond the binary.

Some of that advice though is worth expanding on and using to understand our desire for intimacy, connection, purpose and support so that we can grow with the love of others. Even if you don't want to fall in love and do just want to have a lot of sex, then go for it.

Because at the end of the day, our relationships should make us better people.

Until next time,