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Dimples can occur naturally on the outer corner of the lip or further up on the cheek. Figure out which look you want and estimate the best place to make your fake dimples.  Most natural dimples fall near the natural outer crease line of a smile. To figure out where dimples like these should go, smile in front of a mirror and pinpoint the accompanying creases. The dimple should go just outside of the creases on either side of your face. For dimples that fall just to the outside of your lips, smile in front of a mirror and look for the smaller, inner creases that form just to the lower outside of your mouth. A fake dimple could be positioned along the inside curve of the creases on either side of your mouth. If you have a hard time keeping an eye on the spot, you can make a small dot with your eyeshadow applicator or eye liner pencil to mark it. This dot should be as small as possible to prevent it from interfering with the final look. Take a matte eye shadow or eye liner pencil and draw a small comma on your desired location. Draw lightly at first; it will be easier to darken your dimple later than it will be to lighten it.  Use a dark brown color for best results. Make sure that the color is matte. A glossy or sparkly cosmetic would not be suitable since it will make your fake dimples stand out too much and look too fake. Likewise, color other than a dark brown might also look fake. The period or dot portion of the fake dimple should follow the natural curve of your lips when you smile. Imagine an invisible, diagonal line connecting the corner of your lips and the crease of your smile. The intersection of this line with your smile crease is the right point for your period to go. Draw the tail of the comma directly below the period portion. This tale should be 1/2 inch (1.25 cm) or so long, and the curve should be about as subtle as the curve of your fingertip. Blend the cosmetic into your skin to make it look more natural. Start with a small makeup brush, applying even, rounded strokes that follow the curve of the mark. Fade the edges after you finish with the small brush by using a larger brush. Apply similar strokes with your larger brush. If you cannot achieve the subtlety you want with your brushes, smooth the mark in further with your ring finger. Use the ring finger of your dominant hand since your other fingers may not be able to apply the right amount of pressure for adequate blending purposes. You should continue blending along the curve of the fake dimple, rather than blending against it. Create dimples on both cheeks for a more symmetrical look. If the marks are too light and the fake dimples do not stand out enough, you can apply more eye shadow or eye liner in the same spot and in the same manner.  The right level of darkness can vary depending on why you want your fake dimples. If you want to wear them out and about, you should make them fairly subtle. Fake dimples that are too dark tend to have an obviously fake look. On the other hand, if you only want fake dimples for a photograph, you might want to consider making them a little darker by using several applications of eye shadow or eye liner. This is especially worth considering if you are taking the photograph in poor lighting. These fake dimples will show up regardless of whether you smile or not, but a beautiful smile is the icing on the proverbial cake and can take your fake dimples from “okay” to “glamorous.” You should also smile immediately after application for the purpose of checking your fake dimples. Take a good look in the mirror and determine if you have achieved the appearance you were hoping for. If not, do not hesitate to wash the makeup off and try again.

Summary:
Figure out the right placement. Draw a comma on your cheeks. Brush in the eye shadow. Repeat as needed. Smile.