What are your life’s could have, should have, and would have things or occurrences?

Took more high school and summer school classes than the one year in Edmonton. Also when I was living in Jasper as a young adult I should have taken a forth year of high school.

I wish I had pursued that college degree, but I honestly think I did better without it.

I met this girl in sophomore year of college. She was a petite, sexy, quirky redhead. Not in a cute, Zooey Deschanel kind of way, but in a “holy shit, she has issues” way.

One night there was a party, and Anna and I got separated from the group. We ended up in a 7–11 parking lot sharing a pint of ice cream, and had this long, late night heart to heart. The long late night heart to heart is my kryptonite. At one point, she was talking about her ex boyfriend, how he always looked out for her, and how she kind of liked having a strong person there to protect her, and how she had a troubled past of course. And how she wished she could meet someone like that again. There was a certain look in her eyes. I’ve experienced this about a million times with dudes, where a person gives you ~the look~ when you’re having ~a moment.~

Anna was giving me the look. At that moment I wanted to cuddle her and have her know that everything would be ok. And paradoxically, I also wanted to do unspeakably dirty things to her. Is that what it feels like to be a guy? I almost blurted out, “I could be that person,” but something stopped me.

Instead, we both went home to our separate rooms. I made out with her a couple times afterward, but it wasn’t the same. She got a boyfriend pretty soon after that.

After seeing her with Brian, I’m sure she would have been the worst girlfriend in the world and totally ruined my life. She whined at him all the time and constantly manipulated him into spending money on her, so he was always broke. She claimed to be descended from Princess Anistasia and got upset if people didn’t believe her. Later on she bought two ferrets, and made him keep them at his place (ferrets smell!). Another guy friend started calling him the royal stablemaster, and the ferrets the royal steeds. She had new food allergies and diet restrictions every week. They went raiding together in World of Warcraft, and she would make him go home when we were all hanging out so they could both log on together. They had matching Russian usernames. Brian was pretty much her bitch, and he became the butt monkey of the group because of it. She was spoiled, high-strung, dotty, and temperamental.

Clearly I dodged a huge bullet. But damn, I kind of wish I had danced with the devil.

I could have been a woman, I would have played with my breasts, I should have known better.

I should have availed myself of a lot more sex when I had the chance.

I always wanted to be somebody, but now I realize I should have been more specific.

Lily Tomlin

I should have brushed my teeth the day that I fell in love and had an opportunity with the one that got away, and I should have kissed her when we were playing chess in her dorm room instead of smoking her two games to nothing.