Oops, I did it again…

I’m frustrated.


I once again frustrated myself in my dating life. Which explains why I disappeared and abandoned this blog without a word. Previously I declared that part of the purpose of this blog was to help curb some of that frustration, but when you go sprinting out of the gate like I did, it’s hard to maintain that enthusiasm in the long run.


In 2017 prior to starting my blog, I went on a 6 month dating hiatus. This was the result after having my heart broken by the latest edition of Mr. Emotionally-Unavailable. He, in a lot of ways, encompassed what it is that I’m looking for as per my previous post. In fact, he was the living embodiment of it that proved to me that my idea isn’t so far-fetched or unrealistic. The only thing missing in our relationship was the willingness on his part to take a chance. That bummer aside, I took the time during my hiatus to lick my wounds and to occasionally engage in some self-destructive behaviours. I even managed to develop a rebound crush on someone I met by chance while on vacation. Unfortunately there is no future there so I’m not pursuing it, but crushes can be a nice break from reality.


So when 2018 came around, I was ready for a new start, one that I grabbed hold of with great gusto. I told myself I would get back in the dating game and start a blog to keep me motivated and sane during the experience. So I started this blog and downloaded multiple dating apps, since you never know which app Mr. Right is lurking on. Yet less than two months out of the gate, I was over it. I stopped opening the dating apps and felt no inclination or motivation to even do so.


“The definition of insanity is to do the same thing over and over again and expect a different outcome.”


That’s how I felt when I was on dating sites. I’ve been on and off various sites all throughout my 20s, and here I am closing in on 30 and still cycling through the same sites (and occasionally the same people), hoping for a different outcome. My cousin who recently got engaged, met her fiance through a mutual friend. She too had struggled in the world of online dating and suggested that I take a step back and go “old school” by meeting people through friends. An intriguing and promising idea. I’ve floated the idea to some friends and family and most have come back with the same answers, “I don’t know anyone decent who’s single,” or “the people I do know aren’t ready for something serious.” Welp, that was short-lived.


Honestly, it was hard not to get bogged down by the enormity of it all. I wish I was one of those people who dated casually all the time, maybe then I wouldn’t spend so much time thinking about the big picture when I do meet someone with potential. However, I’m also not the type of person that needs someone. Being in a relationship is a nice to have, but if I have to go it alone then that’s fine too. I’m perfectly fine with going to events and doing things solo. It’s all I’ve ever known really, which means I never feel like I’m missing something, and since I don’t give a flying fuck about what people think, I’m pretty content in my day-to-day life as it is.


However, my parents have been making comments and suggesting its time I got married and “made something” of myself (as if the solid education and good job isn’t enough). My parents are immigrants and they measure success by the number of children you produce. My mother is also a hopeless romantic and every time I start to date someone new she automatically thinks he’s the one and that I’ve found the love of my life. After a few dates she expects me to announce the undying love between Mr. Right and myself and cannot comprehend how I don’t even know if I like a person after a few dates. She thinks dating is like the movies and always digs for details. I know she does it with the best of intentions, but it only adds to the pressure while dating. Another factor I need to take into consideration. Having all that in mind makes dating seem like an insurmountable task.


Hence my unplanned hiatus once again. I had reached a new low. I constantly felt like dating was impossible and that all hope was futile. Most of that feeling stemmed from the fact that I had no confidence anymore. Despite the 2017 dating hiatus, I wasn’t ready to date. I had spent that time wallowing and licking my wounds instead of building myself back up and reassessing what I wanted. As a result I decided instead to change focus. I’ve spent the last 6 months focusing on me. Slowly I’ve regained my confidence and my sense of control over the things in my life. I’m still a work in progress but at least I’m at a point now where I’ve built up enough resilience and patience to get back into the game.


So here I go (again)! Wish me luck.



So I know I’ve vaguely referenced “it” in my earlier blog post, but I haven’t actually spelled out what it is that I’m looking for while dating. However, before I go into what I think “it” means, let me first give you a better idea of who I am.


First of all, I wouldn’t exactly describe myself as outgoing (friendly, yes, but that varies depending on my mood). Despite this, I’ve been told that I possess a quality that puts other people at ease which makes them feel comfortable opening up and to be themselves. Now I’m not sure what exactly it is about me that makes others feel that way, but it could be because I see myself as an open book. I have nothing to hide and regret very little, so I can be pretty forthcoming once I warm up to someone (again depending on my mood, we all have those anti-social days, don’t  judge me). It’s the same while dating. The way I see it, I need to be my most authentic and genuine self while dating. It means putting myself out there in all my quirky, talk-to-much, know-it-all glory. If I’m busy pretending to be someone else for the sake of impressing someone, then I’m going to have a hard time keeping the act up if things progress. I’ve come to realize that anyone can pretend to be someone else for a few hours. I can pretend to be a natural born sous chef whipping up meals on a dime, when in reality I probably ordered take-out. I can pretend to be the most patient/ understanding/ laid-back person by telling you “its okay, you can leave date night early to go hang out with the boys, it’s no biggie,” when in reality I’m thinking ‘leave early and I will actually cut you in your sleep.’ If we can’t be our raw genuine selves with whomever we’re involved with, then what’s the point? Especially if the ultimate goal is to find a long-term commitment. Managing other people’s expectations and perception of you is all good and well until you’re living together and you can’t hide your true character anymore. Can’t hide the emotions, the insecurities, the pet peeves, or the weird habits you have like twerking to the countdown on the microwave while your 1-minute rice cooks. All this to say, I don’t hold back in my dating life (or in my regular life for that matter); what you see is what you get. I’m very frank. If I like someone, I want to spend time with them.  I hate playing mind games, hating the power plays, hate beating around the bush. Ask me what I want and I will tell you.


“So what do you want?”


I want a best friend. A partner in crime. An equal. I want someone I can connect with on a such a deep emotional, intellectual, and spiritual level that the physical becomes a bonus. I want someone who is going to be my best friend before anything else (in other words before life gets in the way, because it inevitably will). The physical aspect isn’t everything – it’s important, don’t get me wrong, but it’s not everything. Relationships come with an endless amount of intimacy in various forms, but I don’t want physical intimacy to be the only thing that binds us. I want my partner to walk through life side by side with me. I don’t want someone who is going to raise me up on a pedestal to worship me and make “taking care” of me as their sole purpose of existence, because I’m a strong, independent person capable of doing that on my own. In essence, I don’t want someone who is going to become consumed with my life, just like I don’t want to be consumed into theirs. I also don’t want someone who will walk ahead of me, being the alpha male always in charge, making decisions without me and expecting me to dote on him hand and foot. I want someone who is also strong and independent, who sees me as a formidable equal and ally who would be a great addition to his life.


“But doesn’t being a relationship undermine the independence? How can you still be independent while in a relationship?”


Being in a relationship doesn’t mean you will or should lose you own independence. In fact I believe that maintaining an independent identity while in a relationship is necessary for a healthy relationship. Like I said, I don’t want to lose myself in another person and wouldn’t want someone else to lose themselves in me. That being said, I’m not saying that I want to always live my own life without having to answer to someone, obviously there are things that should and need to be shared. But if I want to have a girls’ night I shouldn’t have to feel guilty about it, just like I wouldn’t want him to feel guilty if he wants a boys’ night. Similarly, just because we go to parties together doesn’t mean I want us to be attached at the hip. I’m a social person (most of the time), I like talking to people and like moving from group to group. I don’t want to turn around and see him sulking in a corner, or observing me and becoming increasingly jealous, or have him refuse to come along to events altogether. Being in a relationship doesn’t mean you need to be dependent on each other. Being dependable and being dependent are two very different things. I want someone who is dependable, reliable, honest, forthcoming, communicative, open, and willing. I want someone who is willing to swim upstream Shit Creek with me when things get rough. I don’t want someone who is only ever going to send words of encouragement from the sidelines because he’s afraid to get dirty, or someone who’s only ever going to pull me out to swim for me, and definitely not someone who is going ignore the fact that Shit Creek even exists. Life gets rough. One could even argue that the whole point of life is to suffer and endure. Being in relationship often means you endure things together, but occasionally there are things you need to do alone. You will have your own personal battles you need to fight, same as your partner. Your partner should be someone who is willing to endure it with you, but also allow you the time and space to fight alone. They shouldn’t be responsible for fighting your battles for you. They should not take a completely hands off approach. Sometimes all you really need is support, someone to jump into Shit Creek to swim alongside you, and someone to embody the security and comfort of knowing that you are not alone.


The way I see it, if you’re best friends with your partner before anything else, it makes your bond that much stronger. Your bond will go so much further than whatever suffering you’re currently enduring that it will help you get through it, and stop you from throwing in the towel at the first sign of things going bad. I want someone who has a sense of humour, who isn’t afraid to speak his mind, who can keep me grounded and centered, and someone who motivates me to be the best version of myself. I want banter, laughs, vulnerability, security, honesty, support, freedom, independence, partnership, teamwork, passion, an equal, a partner in crime, a best friend.


That shouldn’t be too hard, right?




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“So, what do you like to do for fun?”

“So what do you like to do for fun?”
Nothing. I have no hobbies. Actually, that’s a lie, I do have a hobby. Want to know what my fucking hobby is?
Want to know what the fuck I do in my spare time?
Do you know how much fucking work goes into dating?!
A lot.
In other words, if I’m not at my actual day job earning a living, eating, or sleeping, I’m dating. But I can’t say that while on a date or talking to a new potential date. Dating is like a full-time job with no benefits (k, sometimes there is the occasional benefit). In other words, once I finish work I’m basically coming home to work my second job. A job where I’m, in essence, volunteering. Matter of fact the process of dating is like job hunting. If I’m not actively on a date, I’m screening potential candidates for the next one. I spend my evenings reviewing profiles, trying to determine if the potential candidates meet the minimum requirements of the job, and assessing their skills and competencies to see if they match mine. I spend hours trying to determine if they lied on their resume and if they would be a good fit. I’m going on dates actively interviewing said candidates, usually armed with a list of predetermined questions, so that I’m not that jackass saying “that’s cool…coolcoolcooliocoolcool” to get through the awkward silence. Majority of the time after a short conversation or at the end of the date, I’ve come to the conclusion that the candidate is not the right fit and/or doesn’t meet the requirements, which means I’m now sending the standard job application rejection email in the form of a text message. During no part of this process am I having fun (k, sometimes there is the occasional fun). Stop fucking asking me what I like to do for fun. Dating you is supposed to be fun, and it’s taking up so much of my free time that I don’t have time to have a casual hobby. Honestly, what the fuck are you expecting me to say? Do you want me to say I volunteer three times a week when I’m not out walking dogs, learning guitar, recording YouTube tutorial videos, or taking part in the neighbourhood watch?! I’M PROBABLY FUCKING SLEEPING.
What happened to the art of conversation? When did it become so hard to get to know someone? Meeting people has become the easy part, getting past the pleasantries and small talk is where it gets complicated. We use dating apps to talk to new people everyday, yet somehow I find myself having the same stale ass conversation with multiple people. Conversation and communication is a big deal. I know I talk a lot for just one person (ask any of my old teachers), but that doesn’t mean I’m willing to talk for two. If the conversation is stale, I’m going to lose interest. If you constantly give me one word answers and don’t make an effort, I’m going to move on. But worst of all, if you ask me a dumb, basic, small talk type question, when I’m actively trying to get to know you, I’m going to lose my shit. Your teachers lied to you. There is such a thing as a stupid question. Some questions are so stupid that I am literally rolling my eyes and asking myself, “How the fuck do I respond to this shit?” So here’s a lesson in questions that people need to stop asking ASAP. If you ask me any of the following be prepared to see me automatically triggered:
“Have you met anyone on this app? Any luck with this dating app?”
Plenty actually, that’s why I’m back, couldn’t figure out how to leave a review on the app store so I thought I would just pass on my success story by matching with as many people as possible.
“How are you still single?”
Good question, I’m actually taking a poll, would you like to anonymously provide your feedback?
“Why are you single?”
Uh…why the fuck are you single!? Is it because you ask dumbass questions like that?
“Why are you on tinder?”
To find my biological father, Maury Povich was unavailable.
Stop asking me “so what are you doing right now” every motherfucking hour. I’M WATCHING NETFLIX. Now look, you got me fucked up and I missed what Eleven said. Now I have to rewind and wait for Stranger Things to buffer again. Stop asking me the same basic ass question over and over again.
“So what are you doing now?”
“So what are you doing now?”
“Without me?”
“So what are you doing now?”
“So what are you doing now?”
Thank you for your time and interest in this position, I was very impressed with your capabilities, however after much consideration I have concluded that I am unable to offer you the position at this time.
It’s time to relearn how to make actual conversation. Before you say something, ask yourself the following:

  1. “Is this significant input to the conversation?”
  2. “Can someone respond to this?”

If the answer to either of the above is no, then don’t bother. Don’t text me some dry, stale ass sentence for the sake of saying something. My mother always told me if you have nothing nice to say, don’t say anything. I would like to extend that lesson to if you have nothing relevant to say, don’t say anything. Small talk is not conversation. It’s the shit you say while you mentally determine the quickest escape route from the situation. If the next thing you’re about to say cannot naturally evolve into a stimulating conversation, its small talk. Fuck small talk.
“I need a coffee.”
K…do you need me to point you to a Starbucks? You know they have a store locator function on the website, right? Is this what passes as flirting now? Caffeine is no joke, I will cut a bitch for my morning coffee.
“I hate this weather.”
K…do you need me to have a conversation with the Mother Nature? Maybe you should move, or put on another sweater.
“I know what you mean”
Do you though? Maybe if you did you would have had some input or insight to add. I’m a pretty articulate and insightful person, you should try it sometime.
“You need a glass of wine.”
After this stale ass conversation I think I need the bottle, or a lobotomy, what’s quicker?
“The weather is so nice today.”
GOOD! I’m glad my conversation with Mother Nature benefited you.
“I just ate”
CONGRATULATIONS ON NOT STARVING! Would you like a gold star? I bet your mom is super proud.
Now I know my mother wouldn’t exactly be proud of the internal dialogue that goes on in my head (to which I counter with “I didn’t actually SAY it, mom, just thought it”), but it’s shit like this that forces me to make small talk and general pleasantries. Something that quickly becomes frustrating when I’m actively trying to get to know someone, and that someone is making a blatant effort to not open up or try. So if you haven’t already picked up on the lesson, it’s this: dating requires you to give a fuck. At least one. So if you really couldn’t give a flying fuck in space when it comes to actually getting to know someone, put that disclaimer out in the beginning. If you do give a fuck and genuinely want to get to know someone, then put in the effort and actually engage in the conversation. Genuine connections don’t happen overnight, or materialize out of thin air. To find a meaningful connection it means you need to open up, show your true colours, show your personality, be vulnerable, be an engaged and active participant. The passive approach is why we’re all stuck having the same conversations. Your passive approach is making me aggressive, and I’m all quickly running out of pleasantries.


Frustrated with dating?

Frustrated with online dating? Tired of being ghosted and/or having to ghost others? Fed up with all the lacklustre connections? Happily committed but curious about the world of online dating/secretly love reading TinderNightmare stories and can’t get enough?! Welcome, you’ve come to the right place.

You are now reading my latest attempt of keeping myself sane post dates in the hopes that I won’t have to resort to looking up old Miss Cleo videos to get advice on my love life (if you don’t know who Miss Cleo is you’re too young for this blog bro….if you’re still not sure if you’re too young, and didn’t get the “too young bro” reference, then you’re definitely too young). Now, I’ve been in and out of the dating game for some time now and have learnt a lot during that time. Unfortunately I, like many others, become frustrated when I find myself back at the starting line. In the past I would take time to step back from dating altogether, and then proceed to spend the next 6 months convincing myself to get back in to the game. Ultimately I’ve come to realize that this approach is ineffective (no shit, Sherlock). It means I’m closing myself off to possibilities, and if I’m closed off, I won’t be receptive to what might be coming my way (how’s that for a Hallmark card). In other words the purpose of this blog is to channel my frustrations (and hopefully that of others) so that we can remain open to possibilities. The goal here is to find true love, in a world where catching feelings is the equivalent to the plague, yet we all somehow have a secret list of #baegoals we hope to achieve.
Throughout my dating journey, I have used various dating apps. Tinder, Match, eHarmony, Bumble, Plenty of Fish, OkCupid, you name it, I’ve probably tried it. Dating apps are a double-edged sword. A bitter-sweet experience. Our most useful tool and yet our biggest problem. Dating apps makes meeting people easy. Too easy. Just a few swipes, and I get to talk to someone new, who also swiped right on me, which means they also think I’m cute! Hooray for ego boosts! Talking to someone new is always exciting – especially when you’re still feeling the effects of the ego boost. Suddenly you’re desirable, witty, charming, the most interesting person, and so is the person you’re talking to! Time to start scratching at the surface to find out if there’s a deeper connection there, but wait, there’s a new match! Now you have someone new to talk to. Forget the rapport you’ve built with that first person, it’s irrelevant, because there’s someone newer and more exciting to talk to! Time to start scratching the surface again! Hark! New matches! New surfaces to scratch! Scratch, scratch new match, I’m coming for your heart! Time to drop that cheesy pick-up line I heard on the radio and wait for a reply.
Are you getting the picture yet? Can you envision the cycle? Maybe I should just draw it out… Nah, you’re an adult, use your imagination. It’s important to note that this is a two way street. The people you’re talking to are also doing the same thing. Now you’re asking yourself, so what does this mean? Why do I care? Who the fuck is this person and why am I still reading the shitty blog of someone who’s too lazy to draw a picture for me?
It means we’ve developed the habit of shallow conversations and interactions. We’ve grown so accustomed to only ever scratching the surface, and wading through the shallow end, that we don’t know how to go deeper when we need to (not that kind of deep, you pervert). Have you ever been on a date scrambling to think of things to talk about in order to fill the awkward silence? Ever asked yourself what the fuck people in relationships talk about all day? Seriously. What the actual fuck do couples talk about all day? I see my brother texting his girlfriend all the time. ALL.THE.TIME. HOW DO YOU HAVE SO MUCH TO SAY TO EACH OTHER?! What could have possibly happened in the last 2 minutes between your text messages that you felt the need to articulate it in yet another text message?! I’m out here texting people about the fucking weather like I’m some sort of fucking expert. You want to know what’s next in my arsenal of topics?! The fucking traffic on my drive home and how “good” my day was.
Speaking of texting, it also doesn’t help that we’re a generation of texters and communicating on our own time. We would rather text than talk to someone on the phone. Talking on the phone is awkward, and God forbid they don’t answer when you call. What if you have to leave a voicemail?! Even in my professional life I need to rehearse what I might have to leave on a voicemail so that I’m not cringing for an hour afterwards, and even then I fuck it up and I’m left questioning my life choices. Texting is easier, I can think about what I want to say and there are fewer inhibitions. There’s a degree of anonymity. I don’t have to deal with any immediate repercussions or reaction. Confessing secrets to a screen is more comforting than voicing them out-loud to a person. It’s also easier to have engaging conversations when you have time to think about what you want to say before having to commit to it. In the end it means when we finally do meet, it’s awkward. Suddenly the screen buffer is gone and we’re no longer strangers. We’re grasping at topics, being forced to respond in real-time, can’t google things to sound smarter, or refer back to your social media profiles (because we’re also all huge fucking creepers). Now I’m that jackass on the date filling up the awkward silence saying “thats cool….coolcoolcooliocool…,” until I can think of something else to say.
What was once engaging and exciting via text message suddenly fizzles out in person. Granted, things can fizzle out for a number of reasons: there was no real connection, the person gives you a weird vibe, they might turn out to not be as nice/ cute/ tall/ funny/ interesting as you thought, or you weren’t even that interested in the person to begin with because you have a few other matches on the go that you’re scratching at, and really you just thought, “YOLO, why not, let’s see where this match goes,” but really you’re more interested in tinder match #53 – he has the most adorable puppy and if you’re good he might just let you play with it and pet it (I’m talking about an actual puppy, perverts). Either way we’re back at square one, swiping, scratching, talking about the weather, swiping some more, talking about how “good” our day was, trying to swim deeper but ultimately bailing for new waters while still in the shallow end, all in the pursuit of the elusive “it” (not the clown, I swear).
Well, I’m here to tell you that you’re not alone. Dating sucks. Dating is hard enough with or without dating apps. I’m also here to tell you that dating apps are not your friend. They end up becoming something you use when you’re bored, and the more you use them while bored the deeper you will fall into the never-ending cycle of surface scratching, and the more elusive “it” will become.
So buckle up young grasshopper, I’m your Sensei, and I’m about to drop some dating truth bombs.

P.s. follow me on Instagram @the.dating.diary or Twitter @thedatingdiaryj