Photo from

You don’t have to be an expert to give (good) advice

You just have to pay attention

This is a long post about human relations, self awareness, pickiness, perspective and ultimately learning to let go. From the ground level, and from a single guy.

Part 1 — Craigslist personals and online dating
Part 2 — No experience, or no perspective?
Part 3 — Growing up, learning a better way, and breaking down your picky mental barriers
Part 4 — Let the right one in (aka “you know you’ve learned the lesson when you can teach it to someone else”)

Part 1 — Craigslist personals and online dating

I used to spend a lot of time on Craigslist. A LOT. Like, I’m ashamed of how much time I spent on there. I would spend entire DAYS, (similarly to how I once used to apply for jobs as well). One mistake I know in retrospect that I was making, aside from being kinda desperate (I’m human, not perfect) was that I would reply to any ad that had anything in it that appealed to me. Even if it was only one thing.

She likes board games but isn’t into anything else I like? Screw it. Email her.

Not only would I write my email, I’d usually spend no less than 20-30 minutes on each email, carefully sculpting it to be eloquent, intelligent, funny and casual (I will admit, I failed at at least half of those things most of the time, I’m sure).

I would even write emails, and then completely delete them and start over. I was spending an hour of my life, writing essentially a cover letter, to a complete stranger - one whom I knew little about - and possibly only had one thing in common with for sure, and I was putting myself completely at their mercy. If you can’t see what is wrong with this picture — congratulations — you are me 5 years ago!

Some lessons take WAY too long to learn, but better late than never. My withdrawl from Craigslist was slow and drawn out, but eventually I got to the point where I only checked it once every couple of months, then every 6 months, then to a point where I don’t even remember how long it has been.

And as with being in a toxic, emotionally manipulative relationship with someone, you often have no idea of just how messed up it was until you’ve been away long enough to get it out of your system and have clear perspective on it looking back.

I just logged into Craigslist this morning, and my goodness, it saddens me. I still remember the psychology I used to have looking at this screen, but couldn’t feel much further from that looking at it now. It’s an entirely different world view, and to look back at the people who are still where you came from, but yet to learn the lessons you have by this point, it’s a bit of a punch in the heart (well, if you’re an empathetic heart-on-your-sleeve type like me anyway). I feel bad for them because everyone deserves to be happy, and I don’t think they are going to find happiness there, or at least the chances seem slim.

I am no relationship or dating expert, FAR from it, but I have learned enough things via observation (and pattern recognition) that I learned to see warning signs at a glance without thinking too hard about it. Quite honestly, looking at this screen (the women for men page in the LTR section of Craigslist for my area), I can’t help but feel like I am looking through a one way mirror at a room full of vision impaired sad humans who have yet to learn some very crucial lessons.

Of course, I clicked on a few links to see what the ads said, and to their credit, it seems these particular women are being efficient and just typing 2 or 3 sentences about themselves. Whenever I posted, it was always at least 3 paragraphs. To quote the internet: “Adam, you were doing it wrong”. I know!

I get that people are busy, and even moreso I get that many people would rather not waste time in bars or clubs trying to meet someone good. At the same time, I get the sense that some of the people posting on Craigslist could be fairly assessed as lazy or socially under-developed, in regards to dating. I was definitely on there largely because I was not socially strong, but I can’t apply that same judgement to everyone else on there.

Look folks, I’m going to share with you a secret that I have figured out through years of trial and error (mostly error) — just putting a message or profile up online (potentially unless you are one of the lucky few to win the genetic beauty lottery) and expecting your ideal match to find it and message you… is very unlikely, I dare say impossible. You MUST put yourself out there. I seem to lack on paper, but in person I’ve done much better (thanks to years spent working on my social skills). I’m busy, I don’t like crowds or busy, noisey places. My introvert battery runs out pretty early in the night (I get up between 5 and 6 am for work), but when I have made the effort to go out and mingle, I’ve had a good time and usually always met some cool people and had a good conversation with them.

Coupled with what I know of my own psychology when this was my regular stomping ground, and the fact that that psychology largely seems to still be the primary psychology of others posting there now, the prospects do not seem very good here. Not to mention the abundance of women, ranging from early 20s to late 30s who specifically mention marriage/kids or asking why they can’t find a nice, honest guy… This site really seems like a negative psychological feedback loop, and no matter how many rom-coms you watch, things don’t change just because you keep wanting them to or hoping they will. You have to break that loop!

That said, I DID meet more than one sane, reasonably well-adjusted (often better than myself at the time, honestly) woman on Craigslist, it’s not ALL bad, but it does appear to be overwhelmingly so. And knowing how complex humans are, and the existence of sites like OKC with matching algorithms, I think Craigslist is largely inferior now (if you’re going to go the online route). It provides very little information, it’s essentially like a blind date in text form, and you rely solely on the presumption that both parties are being honest. Of course I have observed people being picky and flaky on every platform, so that’s not exclusive.

Part 2 — No “experience”, or no “perspective”?

Over the weekend a friend of mine alerted me to something she found in an OKCupid profile. One of the (many) questions the site uses to match you with potential mates, is “would you consider dating someone who hasn’t been in a relationship?”.

She found a guy who had answered “No, at this point my peers have been in a relationship, I’m not interested in coaching a newbie”.

I was taken aback by this response, which seemed short sighted and selfish to me. So I ran it by some other friends, and was kind of surprised by their responses, which largely agreed with him.

BUT, the interesting thing that I think is missing both in his response and in theirs, is perspective. Why? Well, on one hand yes — having a lack of experience can be problematic, but only if the person in question hasn’t learned anything on their own (or worse yet, hasn’t even tried to).

To tell you the truth, I have very limited “formal experience” in dating. But I know that I’m capable of it, for the same reason that I know that there are people who have lived twice as long as me, but are less mature — because I observe and I learn from the world around me, not everyone does. Same as you don’t have to go to college to be able to work or start a business. There is more than one way to learn the things you need to know.

So, my stance is, if I meet someone and I like them and they tell me they haven’t been in a relationship before, there are other questions I can ask (much like they ask you in a job interview) to find out if they understand the key concepts and best practices regardless.

My parents are divorced, both have remarried but one runs a healthy, communicative relationship, and the other just yells at and argues with their spouse all the time. From that alone, I have learned healthy and unhealthy relationship behaviour, even without being in one myself. Of course if both my parents were in the latter kind of relationship now, I would lack the perspective that there is a ‘better way’.

So I think this person’s answer to me speaks more of impatience and is short sighted in that it ignores this fact. While there are absolutely some things you can only learn how to deal with in the context of a relationship, most of what you need is just human relations 101 and some decent self-awareness.

I think it is a sign of what I have learned just in the fact that I used to think my only chance at happiness was changing myself to fit someone else and I have learned that my needs are important too, and that I need to find someone who wants to meet in the middle.

I also recently detailed in a post on my website that I have done some soul searching and asked myself some tough but necessary questions, and ultimately decided that I would prefer to focus my energy on projects (such as writing) which I feel can tangibly add value to the world vs spending hours or days, (potentially) futilely chasing the ghost of romance’s future around the internet, to no avail. I am going to do what I think is worth my time, and in doing so, perhaps the right person will find their way to me one day. In the meantime, I’ve been doing something positive and productive with myself.

Part 3 — Growing up, learning a better way, and breaking down your picky mental barriers

It occurs to me how - as I’ve gotten older - I have both relaxed my standards, but also refined them. I’m willing to consider more variations in a partner, but have also learned how to determine what is really worth rejecting someone over (ie is it really a dealbreaker or can I deal with it?). I will no longer spend time writing dozens or hundreds of messages to different women, I will choose much more thoughtfully who to spend time and effort to write a message to. I go for quality. This is largely why I ditched Craigslist and switched to OKC. But no platform is perfect. Sometimes I still spend too much time on OKC, and still haven’t gotten out of it what I am ultimately trying to.

Despite my large lack of actual direct, personal experience dating, I feel like I really do largely “get it”. Many of the problems in relationships that I have observed, seem to stem from one (or both) person’s inability to effectively “manage their shit”. Insecurities, dishonesty, not communicating effectively… I feel like knowing yourself well and knowing your issues (including being able to be honest about them) and developing ways to mitigate or work around them is CRITICAL. That way you’re doing your part for the partnership. After all, you can’t run someone else’s life for them, and I would hope you don’t expect them to run yours for you.

My parents are divorced. My mother and her current partner talk everything through. They’re CONSTANTLY talking about things as they come up, and working on them. My father and his current wife do not. They just yell at each other and argue and never really resolve anything. It is excruciating to watch, and never pleasant to be around. But that’s how they choose to run their marriage.

I have always been picky, as far back as I can remember. With food, with fashion and music choices, with how I’d like my partner to look, sound, think and act. And guess what? Yeah, I’m single. Largely due to pickiness, and because I’ve been sorting out my own shit.

I signed up with a matchmaking service earlier this year, partly in attempt to take some of the burden of searching and choosing, off my hands. I had to fill out a questionnaire. At the age of 29, it was a bit weird. I felt a bit young to be worrying about some of the questions, and a bit old on others. But it was good, because it forced me to think through EVERYTHING. I’d like to have at least rough answers for all this stuff before meeting someone, lest I get into a relationship and figure out that I hadn’t considered something that turns out to be a dealbreaker.

The big ones are usually stuff like marriage, kids, politics and religion. I know how I feel about all those things. The question is, if we don’t match up perfectly, can we get past it? Recently I went on a date with a woman who was loosely religious. I had thought that would be a deal breaker for me, but we had a good, honest, thoughtful discussion and I felt like her beliefs didn’t define her, which was cool. I’ve also come to be kind of a non-traditionalist, so marriage isn’t necessary in my mind.

Same goes for kids, but that’s more because if you force me to choose between my hobbies/interests, and kids, I’d rather be able to continue working on my projects of interest. Not that one is more valid than the other, it’s simply a matter of looking at it objectively — where can I do a better job? by creating something, or by being a parent? If more people had the presence of mind to say “you know, maybe parenting isn’t going to be a strongsuit for me”, we might have a lot less unhappy, improperly raised children (and people) in the world.

[Side note: stop pressuring people to get married and have kids, maybe it’s not right for them, and by pressuring them to do it, you’re doing more harm than good. Sure they shouldn’t give in to your pressure in the first place, but I’ve seen the way some people hound and hassle their friends/family members. Lay off. You’re probably not helping]

I think you get to a point (or you should eventually), where you have enough life experience and perspective, where you’re mature and evolved enough as a person to know who and what you are, and what truly matters to you. You learn what you are willing to sacrifice and what you aren’t. You learn to differentiate between “preference” and “mandatory”. For example - I prefer someone who enjoys exercise, but it’s mandatory that you are kind to animals (and people). I’m still making that distinction on some things.

I had a conversation with a friend months ago, and I told him I knew in my head what my dream woman was like. He asked me “can you see her?” and I said yes. He said “that’s your first problem, you need to erase that image”. I wasn’t sure if I could, but turns out I can, to some extent anyway.

I still know what I find most physically attractive, but there’s a funny trick you can play on your own brain. I’m not even sure how to describe it, but it kind of relates to the Sedona Method which I read about years ago. It has to do with accepting things as they are, and letting go of things you can’t change. Reframing a thought and removing the internal resistance. “I only find X attractive!” becomes “I find X most attractive”. In one case there is only one possibility. In the latter, there are infinite possibilities, but you are still favouring the same thing.

Every time I would see a Craigslist post that said any version of “you must be X feet tall or I won’t date you!” — I won’t be at all surprised if that person never finds what they are looking for. Once you get used to saying (and thinking) “I prefer people who are X feet tall”, instead of “…ONLY 6 feet tall!”, you’ll notice that resistance fade, slowly. I know this because I did it with “curvy” women. I stopped saying (and thinking) that I could never find a curvy woman attractive, and I’ve noticed that I have started to find more curvy women attractive. Still not my ideal, and I don’t suddenly find them ALL attractive, but I can still appreciate them. No one is forcing me to date them after all.

I used to look at women who didn’t fit my preferences and my brain would be like “eww, no way!”. That’s a problem. First off, because that will likely lead to you being unfairly rude, mean or dismissive to the person. You are making a value judgement based on your own personal preferences. This happens all the time in daily life, and many people don’t even realize they are doing it. Afterall, “beauty” is really just what the majority of people mutually agree is visually appealing. But everyone’s definition of beauty is different. Funny, that.

If you re-frame to “well, they are not what I personally prefer, but there are other positives about them”, then you’re less likely to treat them poorly based on personal opinion/preference.

The more specific and uncompromising you are, the less you’re going to get of what you want. There’s a time to be picky and a time not to. Ultimately, I’ve knocked down a few of the pickiness barriers, and I feel better. Less hopeless about finding a match that is still pretty good.

That matchmaker package of questions? I’d already considered many of them, but it put the whole thing in a context that I never had on my own before. I was able, at this point in my life, to be able to take a good hard look at myself, and my wants and needs, and trim some of the fat.

I think many people spend too much time on the ground, close up to specifics of themselves or others, and get lost in these details and maybe can’t get the big picture context to realize they might want or need to make some changes. There’s nothing wrong with admitting that you’ve been getting something wrong. It’s a step towards contentment, fulfillment and happiness. Sitting around waiting for things to change rarely (if ever) leads to things changing.

For some people, this big picture perspective gets forced on them due to certain circumstances, or perhaps when they reach a certain age and certain options are no longer on the table and they have to re-assess. I try to habitually go back up to the top level and look down periodically.

And over time, you get used to looking for good qualities in everyone, not just the people who look, speak, or act the way you like. And as a result, now when I meet people (particularly women) who don’t meet my ideal, I don’t have an instant knee-jerk reaction of disgust or disappointment, I just say “okay, time to find out what other things about them that I like”.

It’s like human relations 101, and it took me a long time to figure out.

I know many will resist the idea. I did at first too.

I’ve been single for several years, and while I haven’t really wanted to be, I have at least gotten to know myself exceptionally well. Where I used to be desperate to make others want to be with me, now I understand my value as a person and in a relationship, and I am going to make sure that I only give my time, energy, love and commitment to someone who is good for me. Whenever I find her.

Past 4: Let the right one in
(aka “you know you’ve learned the lesson when you can teach it to someone else”)

I have recently realized, after writing several responses directly to other people over certain issues, that when you write in response to a specific incident or person, your thoughts and ideas are more focused and directed, than when you decide to just sit down and write about a topic in general. I have written drafts on here before that were general, and then a specific event or interaction led me to write a whole new, focused post on the topic which I think was much more solid.

This post you are reading had been in draft form for about 2 weeks when I saw a facebook post by a guy I met recently (don’t know him very well) about being at the end of his rope, having no luck with women and just desperate for some kind of answer or result. He has apparently been single for a while. Here is what I wrote back to him to try and ease his pain:

Hey, I saw your status from last night, and since I'm in pretty much the same boat (but with perhaps a bit more of a positive outlook) I wanted to shoot you a message.

So, let me hit you straight first off - I'm 29, I have limited “formal relationship experience”. My last “serious” relationship was 6 years ago. So, I know single life well.

In high school, I was far too awkward/desperate, I chased (scared) all the women away. In college I was less awkward, but now for some reason had some kind of ego. If not for a co-worker asking me out at 23, I might still be a virgin. After that relationship ended, I ended up moving to Toronto a few months later. Since moving here, I've dated a handful of women. In every case I was the one who called it off. I had a lot of hangups, and I still do, but I’m getting better.

So, I've spent a lot of time single, and basically it has forced me to get comfortable with it. I could never afford to PAY someone to date (or sleep with) me, and I don't want that either. I absolutely want a real, meaningful relationship with someone great, but being an introvert with a busy, tiring job and having far too many interests/hobbies for my own good, I don't get out all that much (I have to make a point of it).

I've tried OKC, POF, Craigslist, even a matchmaking service. I've met some nice and cool people, but not one that has stuck. I'm still working on me, and have chosen to focus most of my time/energy/effort on personal projects, basically stuff that I'm good at and proud of and can say "well, maybe I'm single but look what I have accomplished in lieu of just laying around having sex all day!"

I wish there was an easy answer. I don't think there is. But the best thing I've done (and thus keep doing) is not dwell on my singledom - make the most of it. I would hate to end up in 20 years saying "I spent my whole life searching for love and never found it and never accomplished anything else either". If love never comes, then at least I can leave behind some kind of legacy.

So that's my advice - whatever you most enjoy doing and are the best at, that gives you the biggest sense of accomplishment and confidence, do that, as much and as often as you can (without getting sick of it). Chances are a woman will eventually see you doing that and be very impressed/interested and come talk to you. The great thing about this is that you are in control at that point. They've come to knock on your door. They want in. You get to choose if you want to let them in. Don’t let anyone in just because you’re lonely. You have to let the right one in or you’re shooting down your own balloon.

I feel like it would be at least partially ironic for me to write a book about relationships, despite my history, but I think I’ve clearly learned a lot of the lessons, and am just waiting to meet the next woman where there is mutual interest and put this all to the test. In the meantime, I’ll be at home, working on posts for my website, or producing my podcast, or reading something new to help keep evolving ideas in my head.

Here is a brief follow-up I wrote after this article.