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Book the first trial before a big night out you don't necessarily have to create a wedding makeup look. The first trial is mostly to see if you have good chemistry with the makeup artist and whether she can follow direction well. She should be able to listen to what you say you like and translate that onto your face in a way you're responsive to. The second trial is when you should do a dry-run of the actual wedding look, closer to your wedding date. Wary of paying for multiple trials? Some makeup artists will deduct trial fees from the final cost of your wedding makeup if you end up hiring them; it's worth asking.
A good makeup artist can guide you toward a flattering look, but if you speak up more during a trial, you give her/him a better shot at pleasing you. It is important for your artist to know as much about you as possible how you wear your makeup daily, what colors you're attracted to, colors that you never wear or dislike finishes that are uncomfortable. Your artist can't read your mind, so don't be afraid that you're offering too much information. Bringing magazine photos of makeup you like might help you convey the look you're hoping for.