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Being a makeover artist, I am often being asked this question. Here is my advice:
Prepare yourself a few hours in advance. Prep your skin well before having your makeup on. This helps makeup stays fresher for a longer time. Do a thorough skin care regime that includes cleansing, exfoliating, masking, toning and moisturizing.
Cover ups. Concealer, foundation and powder foundation is all you need. I love this makeup trick - mixing 'yellow' concealer from Mary Kay with the liquid foundation. It gives the natural color of asian glow and provides good coverage. It is also easy to blend especially for beginners. Just dust off with mineral powder foundation from Mary Kay.
Just add colors. A light stroke of blush and eyeliner with a layer of mascara, you are all set to capture his heart.
Scent. Boost your self confidence with your favourite fragrance. You might want to be careful with the amount of fragrance as during this time of the month your sense of smell is less sensitive. You may not want to drown your date with overdose perfume.
Add that sparkle. If you happen to have a spot on your face, draw the attention away by donning jewels that sparkles at the neck or at the wrist. If you are adventurous enough, wear plunging necklines, drape some long sparkles that plunges into your cleavage.