Trans Cooler Fitting???

[MADED-6]

well i just put my trans cooler on my car and went to run the lines and wen i took them off the radiator they have been flaired outwards.
so my question is how do i get the hose on there?
do i cut a bit off and make it round again then chuck it on there or just try feed it on?
and also how much trans fluid do you think i will lose.
will i be able to drive it around till like monday until im at work where im going to do a trans service?
cheers josh.