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Had to be there 

Probably the most annoying statement said by anyone. A responce to when person A does something and it reminds person B of something else, and he/ she starts cracking up for no apparent reason.
Claire: Sydney, the funniest thing happened yesterday with Anna. We were walking down the street and this hobo looked at us, and we ran away. hahahaha

Sydney: Claire, thats not really funny. It's pretty creepy.

Claire: Eh, I guess so. You had to be there.
Had to be there by ilogin.syd June 22, 2012
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I guess you had to be there 

What you say when someone tells you something he thinks is hilarious but really isn't. You say this to avoid hurting your friend's feelings in breaking it to him that his joke sucks.
Dudeman 1: "Oh man, I was playing horseshoes in Red Dead Redemption and I got a really close throw and John was all like, 'Did you see that!' It was so funny dude!"

Dudeman 2: "I guess you had to be there."

Dudeman 1: :(

You had to be there 

A phrase used as an excuse after someone tells a story that's not funny at all.
Person A: "Isn't that hilarious?"
Person B: "No, I don't really get it."
Person A: "...You had to be there."

You had to be there 

"You had to be there" is a phrase that one often uses when someone asks about a situation/joke/piece of time.

Basically, it means that it's hard to actually explain what that situation was like and that the person who is asking had to be a part of the situation to understand.

TLDR; You should have been there
For example, when perhaps two of your friends have an inside joke without you, and you're curious as to what that inside joke means, and they tell you, "You had to be there" (meaning, you had to be around them at the time when the inside joke took place to truly understand it).

Guess you had to be there 

A response to a story told by someone else that is used to show that it might have been funny, but the way they tell it it doesn't sound funny at all.
Georges: "...and he was like "wait, we don't sell that here, nevermind!" HAHAHAHAHAHAHAHAHA"
Geoff:(doesn't laugh) "Hmm, guess you had to be there."