The night before home date night make the skirt steak marinade. You want it to sit overnight in the fridge. It will help to tenderize the meat.
Take the steak and either put it into a zip lock back or in a bowl which you can cover. We used skirt steak because traditional this is the type of steak that is used in Puerto Rico, or so google told me this. I haven't tried it with Flank steak yet, but I will and let you know how it tastes.
Fresh squeeze the orange and limes and add to the steak. Chop up the cilantro and the garlic and add with the steak. Add everything else and mix it around really good. I've made this in a bowl and a zip lock bag. I think it works better in the zip lock bag. Mine has pineapple in it too, but you don't have to use this. Stick it in the fridge overnight or let it marinate for 8 hours.
When it's time for Home date night go ahead and take the steak out of fridge and lets make the chimichurri sauce
Pull the leaves off the cilantro and the parsley and add them to a blender or food processor. Add the garlic, shallot, red pepper, red wine vinegar, lemon juice, oregano, salt, and pepper and just pulse the blender until it's chopped up some. Slowly add in the olive oil pulsing the blender. You don't want to just kick it on high, then your chimichurri will come out like soup. You want it to have some texture so just pulse it and taste it until you like the consistency. If you need to add more salt just go for it.
In a deep fat fryer or frying pan heat up some oil to 375°. While it's heating up go ahead and peel the green plantains and cut into 1 inch pieces. They can be tricky to peel, so cut down the longer end with a knife and use the blade of the knife to pry apart the skin to get it started. Then under running water you can peel off the rest. Invite a Puerto Rican over to your house to show you how it's done.
Ok, since we want this to all come out hot at the same time you need to start the steak before starting the Tostones. Tostones need to be eaten right away. They usually don't taste good after 20 minutes or so since they've been made. They are best right out of the fryer.
In a cast iron skillet or large frying pan, heat the skillet up until you start to see a tiny bit of smoke coming off of it. You don't need to add any olive oil. Just pull the steak from the marinade and let it cook. You might have to cut it in half so the whole thing fits in your skillet. Cook on each side for 5-6 minutes for medium rare. If you have a thicker piece maybe more time. Don't start the 2nd part of the tostones until you are pulling the steak out to let it rest.
While the steak is cooking add the cut green plantains to the oil. Let them cook on each side until they start to brown and then pull them off to the side. Add more of them each time until they are all browned.
Once they are all browned you can either use two plates or what I call, a tostones maker, to smash the fried plantains into 1/8 to 1/4 inch thick flat pieces. The steak should be done before you place them back into the fryer. let the steak rest for a minimum of 10 minutes.
use a spatula to get them off and then add them back to the fryer
Cook the tostones for around 2 minutes or until golden brown. When finished pull them out and place them on some paper towels.
Once the steak is done resting go ahead and cut it into 1/2 slices with the grain of the meat. This make it easier on the person that is eating it. Then plate up your dinners by adding the chimichurri to the steak and enjoy an amazing meal with the person you love. We also used the chimichurri with the tostones. It was so unbelievably good.