Navigate the Dating Waters with a Dating Journal

Leo Gvnage
6 min readJun 15, 2020

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Dating is daunting. Online dating is daunting. Online dating after two consecutive relationships in ten years was just damned impossible to think about.

Or so I thought.

Last time I had looked at online dating, MySpace was still a possible option for me. Loading up Tinder, Hinge, Bumble– was exciting at first, but I was quickly overwhelmed by information overload.

Well, I am over a year into this, and there IS a way to de-complicate dating. All it takes is a few simple pages in a journal.

Photo by NeONBRAND on Unsplash

The Dating Journal Mantra:

Dating is a means to teach me about myself. Even if things don’t work out, I will gain tools to take with me in my journey forward. I have set boundaries, and I will track when someone violates them, or if I betray them myself.

Onto the journal itself…

The Index

My Dating Journal lives within my everyday bullet journal. Wedged between page 75 or so, I keep the Dating Journal’s index. My dating entries are spaced out between my schedules and other notes that are not necessarily dating related, this way I can keep my written thoughts with me at all times.

If keeping a separate journal or notebook is more your cup of tea, I encourage you to keep it somewhere where it is easy for you to pick up or put down. Either your purse, your work station, etc., so that you do not neglect or forget about it.

Now to get started with organizing the Index:

[1] To begin, I encourage to always always use code names. If someone gets hold of your journal, this will protect everyone involved. These nicknames I use conversationally with my friends or therapist, too. Not only does it protect privacy, but it also is a great tool to lighten the emotion out of a break up. Hard to be too heartbroken over a guy named “Ponytail.”

Just be sure you don’t call your date their nickname. :)

[2] Also, I label each entry by the season I began to date them.

Fall 2019 is F19, Spring 2020 is S20, Summer is Su20, etc.

The Dating Journal Index

The Log Page

Dating entry setup. See filled out version below.

First and foremost, don’t bother with all the work if you haven’t physically met them yet. The Dating Sea is a fickle temptress and best not give attention to anyone until they step up to meet you.

Start with the heading:

[1] Code name. If you are not attracted to just one gender, and are greedy like myself, I also follow the name with the gender identity of the person.

Next, add where you found them (in this case, I found my hot fake date on Tinder). Whether you met this person on a dating app or you found them at the bar Downtown, keep track here. I use several dating apps, so this helps keep them straight in case I need to go back for reconnaissance (i.e., “what the heck do they look like again?”).

Lastly, I add start and end dates for record-keeping sake.

The Prediction:

[2] Other than the Log, the Prediction is the critical part of the dating journal. This section will help you sharpen your intuition into a fine tool for all kinds of relationships. At first, you will likely make some bad assumptions about the people you are dating, especially if you have been wounded in the past or are particularly naive. The Prediction will mature your empathy, while also armoring you against heartbreak.

The Prediction will mature your empathy, while also armoring you against heartbreak.

You will want to add to the Prediction as you get to know the person, and you will begin to foresee the direction of your relationship. Hindsight bias is one bitch of a cognitive bias, and the Prediction section combats it.

How many times have you heard a girlfriend say, “I saw the red flags on the first date. I knew he was bad news!” But did they know better? The answer is: absolutely not. If they saw the red flags written out, right in front of them, weighed with pros and cons, they would have left this person long ago. Hindsight (bias) is 20/20.

Remember, you are the weatherman predicting the chance of rain. A tornado drops out of nowhere, and you find out your shiny new date is actually married and not a plastic surgeon? BAM, no hindsight bias. Nah Girl, you didn’t see that one coming.

When we make predictions, any breakups will not seem like a surprise. You will see them coming way ahead of schedule.

In essence, you are composing a theory, enacting a social experiment, and using the dating field as your laboratory.

The Pros and Cons:

[3] Fill these out as you date them. I encourage anyone to be slow to fill these out, especially since these are the hard facts of the person. The Prediction is the theory-work, and this is the evidence you will uncover as you learn about the person.

The Log:

[4] I began with what I called an “Error Log” in my journaling. This was a general-all-around-life log, and I would track everything from when my boss gave me a pat on the back, or when my ex-husband said something rude to me. The Log has helped me do everything from move to a new state and also leave my ex-husband. The Log will help you take the temperature of your relationships and see patterns.

The Log will help you take the temperature of your relationships and see patterns.

I have a bad habit of only remembering the good parts of relationships, and am quick to forgive, even when said person has not earned it. To have a selective memory, whether it’s only remembering the fights or the good times, is a cognitive bias, and it’s a huge problem in relationships.

Use the Log for the dates, sure, but also use it every time something heart-felt happens or a terrible conversation comes up. Use your log to see how you work through your arguments and if you resolve them. This will track your activity, and you can look back on it with fresh eyes. The Log will help you figure out whether it’s time to let the relationship go, or see it’s worth fighting for.

Last, what did you learn?

When it’s over, it’s time to write what you learned. This is usually whatever empty space I have left over on the page, though sometimes it’s time to dedicate ten journal pages to writing your ex a letter.

You are your own audience, so be raw, be visceral. Do a word dump, or write letters to the person. For some people I am dating, it only takes a sentence or two to sum up how I felt and what conclusions I needed.

This portion is important to also note the things you learned about yourself. Dating is not just to see what’s out there, but it is also a discovery of yourself. Even the worst relationships can teach us something.

Dating is not just to see what’s out there, but it is also a discovery of yourself. Even the worst relationships can teach us something.

Through dating in the past year, I have learned that I can be emotionally unavailable when I am at my worst, but also on the flip side, I loved my ex’s minimalism apartment and pursued to perfect my own. I discovered from a two week fling that I really liked to swing dance, and I eventually switched the type of glasses I wore because a fashionable Algerian date said round shaped frames really suited my face.

Braving the danger can be quite exhilarating. Just don’t forget your Captain’s Log.

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Leo Gvnage

Navigating the chaos. In favor of philosophy, books, and journaling as tools for pragmatic living.