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The grass is always greener on the other side of the fence 

Refers to the way we tend to look at other people’s lives and other things that we don't have in general through rose colored glasses.

Comes from the idea of looking at a neighbours lawn and seeing it as better looking, healthier and overall greener then your own when in reality you’re just ignoring anything negative about it and downplaying everything positive about your own.
Friend#1: You’re so lucky, you went to a great college, have money and you’re so smart and will probably accomplish more by the time you’re 30 then I will in my entire life.

Friend#2: Are you serious? I’ve always envied you. People expect so much out of me. I’ve never been able to have a life because of studying and other schoolwork. If I get less then an A, people freak out like I got an F. I may accomplish that much, but with all the pressure on me I’ll probably be insane by the time I’m 35. In so many ways, I wish I could just be a regular guy with normal expectations and a normal life.

Friend#1: Wow, I honestly never looked at it that way. I guess it's true that the grass is always greener on the other side of the fence.

The Other Side

Opposition otherwise known as “opps” in slang where they are from the other opposite rival area.
“Damn I hate the other side” “Man fuck C.H, he’s from the other side” “you know it’s fuck the other side cuz my niggas gone, always been fuck the other side we don’t get along”
The Other Side by headass_hunter January 14, 2021

as cool as the other side of the pillow 

About as cool as a person can possibly be, sort of like James Dean or someone like that, but even cooler. Possibly originated from SportsCenter. Has nothing to do with temperature.
I was as cool as the other side of the pillow back in high school. I used to sit in the back of the class in my leather Harley Davidson jacket and sunglasses, smoking my Marlboro Reds and drinking whiskey out of a silver flask. I'd just sit back there, all laid back across the seat, with my arms around the two hottest girls in the school. The teacher would tell me to put my cigarette out and stop drinking, and I would blow smoke in her face and say, "Make me." But she wouldn't make me because I was just too cool.
No, not really, actually I was a fucking dork who watched Star Trek marathons and still haven't lost my virginity except for my dog that one time.
No, just kidding again, I was pretty normal, but I always used to look at the other side of the pillow and wished that someday I could be that cool. Sadly, it never happened.

see you on the other side 

See you again after a major objective has been achieved.

This phrase may originate with the Apollo 8 mission, the first time in history humans had passed behind the other side of the moon from earth.
CapCom Gerry Carr spoke to the three astronauts more than 200,000 miles away, "Ten seconds to go. You are GO all the way." Command Module Pilot James Lovell replied, "We'll see you on the other side", and Apollo 8 disappeared behind the Moon, the first time in history men had been occulted. For 34 minutes there would be no way of knowing what happened.

Source: history.nasa.gov

the other side of the day 

The opposite meridiem of the day. For example, if it is 7am, the other side of the day would be at 7pm of the same day. If it is 9pm, then it would be 9am.
ha, you're doing your homework last minute?
no Cece, it's due on the other side of the day.

see you on the other side 

A form of bidding farewell to a close friend or relative when you know that the probability of ever meeting them again in the future is slim and exceedingly marginal, or when you will cease all contact with the aforementioned individual for a considerable time without sitreps.

The phrase was first brought to public attention after Jim Lovell, aboard Apollo 8, uttered the phrase before going dark behind the Moon for 34 minutes. It was later popularized by mainstream media, such as books or films, where the phrase is occasionally used..
Gerry Carr: "Ten seconds to go. You are go all the way."

Jim Lovell: "We'll see you on the other side."