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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.

Sit on the fence 

To decide to avoid making a decision one way or another.
Girl 1: You coming to the movie with us?
Girl 2: No, she's coming to the club with us!
Girl 3: Umm, I need to think about this, I don't really want to have to choose.
Girl 1: She's just trying to sit on the fence.
Sit on the fence by ZMan June 24, 2010

Piss it on the fence 

When someone trys to accomplish something they have worked hard to do and fails in a way that would make that effort seem worthless. Fuck it, fuck that. (Ussually said in a competitive atmosphere after a humiliating loss)
Ex1.
P1: wtf has he been doing
P2: idk tht nigga can not kick flip for shiiit
P4*snaps board attempting k flip down gap*
P3: that's "E"
P2:Piss it on the fences
Ex2.
P1: wtf dude mewtwo is so cheap
P2: really nigga?!
P3: Dude.
P1: Fuck! See dude that same shit every time!
P2: HAHAHAHA gotcho ass with that ghetto ass combo
P3: Jesus Christ this nigga just died at "0%"
P4: Piss it on the fence
Ex3.
P1:Dude I heard u got Tammy pregnant
P2: shhhh damn we don't know yet
P1: *Loud*Nah dude fuk that that's fucked up!
P2: well damn nigga just piss it on the fence then.
Piss it on the fence by Pots&Pans September 27, 2015

sitting on the fence 

existing in a state of uncertainty and ambivalency.
He's really sitting on the fence about his roommate—he might be a great guy, but he might be a real villain...
sitting on the fence by Battlemonk September 29, 2005

Grandma's on the fence

when someone doesn't finish their sentence and leaves you guessing.
-"oh did I tell you about.. never mind I shouldn't say.."
- "Grandma's on the fence here bro just say it."