If I were you I wouldn't shave on Friday. Your face will have an extra day without skin irritation, and for some reason, longer stubble seems a little easier to shave, especially at the beginning.
I would also only go with the grain on your first shave, finishing up with the DE if you have any problem areas. Even if things go really bad, you could always do the easy areas like your cheeks with the straight, and get the rest of your face with the DE.
Once you get more comfortable, you can add across the grain strokes, and if you want to, against the grain.
Your face will probably adjust to the straight within a week or two. The bigger question is how soon you will adjust to the different technique involved in using a straight. Read through the materials posted on SRP and you should be well on your way.
Good luck and let us know how it goes!
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