That is one of the oldest tricks in photography my friend. Its a classic double exposure - done in the darkroom usually but possible to do in-camera. You can probably do it in Photoshop with 2 images. Take 1 of the martini glass up close and then one of the person from a distance.
If you visit the Adorama web site (adorama.com) and click on AIRC (Adorama Imaging Resource Center) and then click on SFX - Special Effects Photography you'll find plenty of examples of double and multiple exposures and how to replicate them in Photoshop. Elinor Stecker-Orel is a former instructor at the New York Institute of Photography.
