Can two student pilots fly together on a flight?
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Very simply, the answer is a definite No!

One day, during my full time instructor stint in the 1980's, I saw our trusty Cessna buck-and-a-half pull up to the ramp after landing, shut down, and I watched two of our student pilots get out. Jovial, smiling, laughing…then the mean old instructor walks up. “What are you two doing?” I asked.

“Just practicing together” was the reply. I informed them that in no way, no how, and at no time are two student pilots permitted to fly together. Not only did my flight school prohibit that, FAR 61.89(a)(1) prohibits a student pilot from carrying a passenger. While they tried to justify that they were both pilots, which was true, I had to educate them that only one pilot is required to fly a Cessna 150, and that the other person on board is considered a passenger.

Except when with an instructor, a student pilot only has solo privileges. If a student pilot flies with another pilot who holds any higher rating, the student pilot is considered that pilot's passenger.

How they both got in the airplane together is beyond me, but you can rest assured they never did that again.

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…and then there's the old story about Charlie and Fred and their pal Jim the FAA Inspector…

So Jim gets a call at the FSDO that there's just been a wreck at the local airport involving an old Apache and a couple of the local Airport Bums Club members he knows named Charlie and Fred.  Jim's a little puzzled how a wreck with an Apache could involve Charlie and Fred because he knows neither holds an AMEL rating, just ASEL they use to fly the Cub they own together.

Jim arrives at the airport to see an old Apache sitting in the grass off the side of the runway, landing gear collapsed, with Charlie and Fred sitting morosely next to it.  “What happened here, boys?" says Jim,. "You weren't flying this, were you?  I know you don't have multiengine ratings.” 

Charlie shuffles his feet in the grass, head hung down, and says, “Well, yeah, we were.  See, the Cub was a bit too slow for the places we wanted to go, and we saw this old Apache for sale real cheap, so we bought it.  We figured that since we're each single-engine qualified, we'd each operate one engine.”

“Yeah,” says Fred, “and everything was going great until halfway down the runway, my engine quit, so I aborted.”

“But mine was fine,” continues Charlie, “so I kept going.”