I’ve done so in the past, but I haven’t in four or five years. The older I get, the more of a germaphobe I become! I’d be okay with using a product from certain friends (e.g. ones I knew who took good care of their products) if it was lightly used (think once or twice).
First, just wear it around the house! Once you start seeing your reflection with stronger/bolder/more colorful makeup on, you’ll get more used to seeing yourself that way. You can work your way up to public forays by wearing bolder looks when you visit friends or have them over.