I am wanting to make sugar cookies for Valentine's Day, but I have never used royal icing. Do you outline the cookie first with the icing, then fill in with thinned icing? If so, what is the best way to get the icing on, would I "paint" it on?

I prefer outlining first and then flooding. You can use fondant too instead of royal icing to cover your cookie.
Edna

I outline first and then flood with a bit thinner RI. Some here use squeeze bottles and love them, but I like pastry bags as the squeeze bottle and I did not get along when I gave it a whirl. If you need a recipe for RI, I really like Antonia74's RI recipe here on CC. Happy baking!

I too use the Antonia74 RI recipe and add 2 TBSP clear vanilla for taste. I outline first and then flood with thinned RI in a squeeze bottle. I like the squeeze bottles. You will just have to practice and find your own style. I am still pretty new at this and have tried the bags and the bottles. It is just personal choice.

flourgirlz: Antonia74 RI or toba's glace, they are tops!! I use bags for thick icing, and bottles for others. I actually outline, let sit a few minutes, then sort of a zigzag motion with thinned RI or TG, then take a toothpick and work it into the outline. Let that dry several hours, and decorate on top of that layer. If you're used to fondant, try some rolled buttercream and RI on top of that. There's so many options with cookies. Looking forward to seeing your first pics!!

Thank you all so much! You have been a great help!!