Get Her a Drink
Whether you are at a relaxed chill-out lounge in Manhattan or at a small gathering with your circle of friends and acquaintances, one casual way in which to let a woman know you are interested is by getting her a drink. No extra talk is necessary, and no expectations have to be attached. As she receives the drink, give her a small smile and then stop looking.
Take Advantage of Technology
One of the biggest benefits of being alive in the modern age is being able to take advantage of technology and all of its perks. For instance, if you know your crush object's phone number or e-mail address, message her periodically with a joke or a laid-back message such as "How are you doing? Just thought I'd say hi." Not only do you save yourself from having to speak in person (and stammering or stuttering), she also can't see you as your face turns bright red.
Get to Know Her
If you have the chance to be able to speak to your desired woman one-on-one, focus on getting to know her as a person. Do not make her think that you are only interested in dating her. Not only does this allow you to get to know her better, it also reduces your odds of feeling shy, embarrassed or rejected. Ask her about her career or schooling. Find out if she prefers cats or dogs, or where her dream vacation spot is. Be imaginative.
Allow Her to Feel Special
One surefire way to make a woman feel good is by paying her compliments. For shy men, this can be done in a subtle way that is not overt. Do not be smarmy or insincere. Tell her you like her speaking voice or that you admire her extensive vocabulary or her way with children. For physical compliments, consider telling her that you like the light green shade of her eyes or the length of her hair. Make her feel special and like she is the only woman in the room to you.
Channel Your Inner Comedian
Without being forced, try to channel your natural "inner comedian." Be witty and keep the atmosphere light-hearted and good-humored, if you get the chance to have an extended conservation with the woman of your dreams. If the atmosphere is light, it reduces any chances of awkwardness that you, as a shy guy, might feel. It also decreases the pressure placed on the woman.