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Swung out of the strikezone and still hit a homer

Keeping with baseball metaphors it is to go after someone far more attractive than oneselves and manage to have sex with them.
Michael: You went after Mackenzie? That's pretty bold she's like a 10!
Sanders: Yeah she is, we hooked up though.
Michael: Oh shit you swung out of the strikezone and still hit a homer.
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still on the bench 

Meaning a lack of experience when referring to "the bases."

1st Base) French - Kissing. Usually with tongue.

2nd Base) Feel - To cop a feel, grope, or fondle.

3rd Base) Finger - Sexual stimulation using the hands. Oral sex could take place after this point.

Home Plate) Fuck - Sex, intercoarse.

Baseball is being used as a metaphor for intimacy. In baseball, if a player is on the bench they are not in the game.
"So, Evan, how did things go with Erica last night?" said Ben.

"It was pretty chill, man. The movie sucked though." Evan replied.

"Did she let you cop a feel at the movie?"

"Dude, I'm still on the bench."

"That was like your fifth date. Shouldn't you be getting a little action by now?"

"Naw man, we're taking things slow."

OH, SPEAK TO ME OL' TOOTHLESS WONDER. YOUR VOICE HAS CHANGED, BUT YOUR BREATH STILL SMELLS THE SAME.

When someone changes themself but is still a jerk.
Katie, oh speak to me ol' toothless wonder. Your voice has changed but your breath still smells the same. That's what I have to say about your "new persona"

If the joint's still lit 

Indicating proud ownership of the fact that one is taking advantage of a situation should said situation provide itself available.
Are you still receiving unemployment insurance? If the joint's still lit.

the jury is still out 

the period of time between sessions with a female, usually a 20 minute power-nap
she wanted to go again but to my disgrace the jury was still out
the jury is still out by Mike January 10, 2004

legally blonde and his skunk head wife and there home alone looking receding line twerp of a son that cries himself to sleep and still wets the bed 

Lucius, narcissa, and draco malfoy
I hate legally blonde and his skunk head wife and there home alone looking receding line twerp of a son that cries himself to sleep and still wets the bed.

still in the fight 

Shits bad, but fuck it you'll live
"Dude I think this car is on fire!?!

"Naw man it's still in the fight!"