The ability to pay attention to the little things is a quality all truly skilled hosts possess. A little bowl for olive pits, a scented candle in the bathroom, and a chilled cocktail glass all show that you care about your guests' comfort and their overall party experience.
Popping a bunch of glasses in the freezer before everyone arrives is a good way to prepare your stemware, but to re-chill glasses as they need to be refilled, grab a bowl, tray, or cooler of crushed ice, and set the glasses down in there. The larger the surface area, the more glasses you can chill at a time, so aim for something with a wide opening.
Pour the ice into your receptacle, then invert the glasses and nestle them down in the ice. Leave them in there for a few minutes, then refill the glasses with your guests' poison of choice. If you only need to chill one or a couple of glasses, you can dump a scoop of ice into a glass, let it sit for the time it takes to make a drink, then toss it out just before filling it up.
Halloween is the best holiday; this is a fact. Kids get to dress up like minions or a Frozen or whatever, stay out late and — unless their neighbours hand out toothpaste, an act somehow not punishable by law — eat a truly unconscionable amount of lollies. Adults can do all of the above and get drunk while watching horror movies, which is my preferred way to observe the day.