Choose a private place for your kiss. Respect that a shy woman may not feel comfortable kissing in public. Create a comfortable, romantic atmosphere. Dim the lights to help her relax. Make sure you won't be disturbed, which would be embarrassing for her.

Offer her a glass of wine or her favorite beverage, whether the drink is alcoholic or not. If she prefers a certain type of wine, choose her favorite, if you know what she prefers. If not, choose wine with a mild flavor that’s not too strong, such as a chardonnay or riesling for white wine or a young Beaujolais or merlot for red. Offer a plate of gourmet bon bons. Look into her eyes and smile gently, and speak in a soft, gentle voice when you offer these to her.

Sit close and chat with her for a few minutes. Make physical contact, such as putting your arm around her or holding her hand. Ask about her day, how she feels or if she is enjoying herself in your company. Give her time to relax. Look into her eyes. This will give her a chance to relax..

Gently brush a lock of her hair away from her brow or loop a lock of her hair around her ear lobe. If she relaxes with this gesture, then you’ll know she may let you get closer. If she doesn’t relax, then pull back and wait for her to signal that she wants you to draw closer. If she gives you long, deep looks, blushes or shifts position in her chair, take these as signs that she wants you to come closer.

Gently graze your chin along her chin line and mumble something in a low voice, when she has signaled that she wants you to get close to her. When you see her lips part, run your index finger gently along her lower lip and then along her upper lip. Watch and listen for signs that she is ready for you to kiss her, such as if she utters a soft sigh.

Nuzzle her neck gently, positioning your cheek over her cheek, and then navigate so that your mouth hovers over hers. Close your eyes and gently touch her lips with your lips. If she is relaxed, her lips will feel warm and full. Linger a moment and then pull back slowly, and enjoy the chemistry that has enveloped you two.

Smile and pay her a compliment, such as "You have really soft lips" or "That felt great." Boost her self-esteem to give her the confidence to enjoy your kisses and perhaps even initiate a kiss herself.

Go for a slightly longer kiss. Stick to lip kissing; don't use your tongue yet. Sex expert Tracey Cox in the article, "How to Be a Good Kisser," suggests covering every part of her mouth with soft, light kisses. Make her feel desired and place your hands on her cheeks, hold her hands or run your fingers through her hair. Look to see how she reacts to your touch, and continue doing whatever she enjoys. Take your time and enjoy creating a romantic atmosphere.