I am answering this as someone who has made some improvement compared to how I was testing a few months ago. I made a similar comment a few days ago when I felt I was unable to maintain long term friendships before my ADHD diagnosis. I am pretty sure this post is going to turn out to be very long because I am bored, drunk and I have decided to comb through your post line by line.
TL;DR : Creating a fantasy is going to keep you stuck in a virtual reality. You need to go outside and touch grass to ground yourself to the actual reality. Recognize and accept the faults that make your friend a human.
when I usually start to notice we have grown bored of each other. Two people only have so many jokes stored in their head, and as you get to know them, they stop being a shiny new toy
I believe you might have gotten the wrong memo about friendships. It is not a joke exchange. Are you attending an amateur comedy night at a local bar ? A friendship can be anything that you want it to be.
I have gotten together with friends to chat about a movie that really opened my mind (for example, Midsommar1), went to watch a movie together (insert any superhero flick), bitched about a movie that was not at all like the book it was based on(World War Z2), bitched about their partner, bash my Ex and then move onto spending time hangrily searching for sustenance. This is just one example which can be turned into an exhaustive list.
Do I love everything that I do with my friends ? No. But my friend is into it and I get to enjoy the experience through my friend's excitement. I am sure my friend could say the same thing about my interests.
How often do you tend to open up with your friends?
I prefer to take things slow romantically and friendship-wise because I grew up an only child. I find it difficult to trust at the beginning but after some time, I start to open up. The people that I call friends are a mix of before and after my ADHD diagnosis. They knew my faults but still accepted me for who I am.
For example, I have noise sensitivity issues i.e. they know to not take it hard if I refuse to go to a club or a noisy bar. There were some that refused to accept this when they were made aware of it. This was typically followed by snarky comments. This was a deal breaker for me because I cannot enjoy an experience through a friend if I am suffering internally and physically.
If/when you do, do you become emotionally-expressive or just state your feelings like facts?
How do you expect them to respond ?
This is a give and take at a sloooow pace. Both you and your friend decide each step of this stage. Your goal is not overshare with the biggest issue you have ever faced. Your friend is a normal human being not a therapist who knows how to deal with all of your trauma. Taking things slow helps your friend understand on how you expect them to respond. Do you want some feedback ? Or do you want to vent and someone to listen to ? You can say this verbally or if your friend is aware of your facial expressions/body language, they can respond accordingly.
Afterwards, does it become awkward or do you feel glad you opened up?
I'm always glad I opened up. A few months ago, I went through a phase where I was too ashamed to talk about how a guy I met on a dating app three months ago was taking me for a spin on a roller coaster. I let myself suffer when I should have opened up to my friends, laughed and cried about it all.
The few times I have regretted opening up, I knew while I was still doing it that it was come back and bite me in the ass later. I have learned from these experiences and will open-up selectively because people talk and I cannot lie to save my life.
How different is my friendship cycle to yours? What differences are there?
The only difference is that I do not get bored after 2 years. This is the stage where I will think I have made a lifelong friend. Grass is greener where you water it also applies to friendships. The more consistent a friend is in showing up and making plans, the more I want to maintain the momentum.
There have been moments where I or my friend did something that was unwise. We spoke up when we were supposed to. If someone was angry with how things were handled, they spoke up about this as well. None of this meant the end of who we were.
There have been moments where I knew significant conflict resolution was required and my friend preferred to ignore it. I do not operate well with a grey cloud hanging over my head and pretty soon the friend became a former friend.
Deciding which friendships to maintain and which to let go was one of the biggest lesson I had to teach myself.
1 Midsommar subverts your expectations about what a horror movie is supposed to be
2 World War Z Movie : You'd better not comment about this abomination