How can a shy person get from here to there, from numb, panicky silence to the point of comfortably being able to joke, laugh, and banter with a woman? How do you develop the talent to reach inside yourself and pull out just the right phrase, the one that resonates, that rattles the windows, that makes the listeners "ooh and ah", the inspiration, the wild card, the slamdunk? It is simply a matter of finding that quiet spot in your mind, the place of refuge, the fortress from which you can sally out and do battle on the field of wordplay.
Comfort level and confidence are the key. It is not terribly difficult to banter with a friend, with a person with whom you are not deeply emotionally involved, or indeed with a total stranger, again with no emotional strings. When you are face-to-face with a woman you would like to know better, tension, nervousness, and the need to "perform" can spoil the game.
Begin by upgrading conversational skills. Keep a notebook of funny one-liners, retorts, and gambits ("Don Quixote at your service. Would you kindly direct me to the nearest windmill?"). Be creative... quips you make up yourself are better than ones you hear or read. Practice your delivery of them, in your own particular style and cadence (not imitating any particular well-known performer) until it becomes virtually automatic. Have a friend or family member "volunteer" to play the role of your conversation partner and drill at pulling returns, retorts and quips out of thin air, and in "real time".
Read novels and construct imaginary scenarios, with dialogs between the male and female characters. Imagine what they would say to one another in conversation, in flirtatious bantering. Rewrite the story in your mind, putting yourself in the place of the male lead. What would you say?
Practice and rehearsal in the theater of the imagination... all this is a crutch, to be sure. Before you can walk under your own power in the arena of raillery, you will need a crutch, an amulet, a lucky charm. This is a device, an magic to unlock your talent and power. Who knows what hidden depths you will uncover within yourself...
Doing it, finally
Let the context determine the script. A woman making a hostile approach requires an entirely different mode of handling than one who is friendly and interested in you. In either case, a smile serves as a bridge toward the interaction that will follow.
Ideally, you will be perfectly matched with a conversation partner, and the encounter will unroll as smoothly as a choreographed comedy routine. You will feed each other lines, and bounce witticisms off each other. It will be enjoyable and productive for the both of you.
He: "Well met by moonlight."
She: "'Tis not midsummer, nor does the moon grace the heavens, nor this a dream."
(Good. She knows her Shakespeare.)
He: "In thy presence, doth not the lilac bloom, the darkest night glow as if moonlit? Melt into my arms soonest, beloved, ere I revert to latter day Anglic, the speech of varlets.
Repartee as verbal self-defense will tax your skills to the limit. This calls for detachment, stepping out of your skin, playing of a role, playacting in the truest sense. Picture yourself just "kidding around" with your kid sister, rather than in a knuckle chewing confrontation with a desirable, but hostile woman. It's a rehearsal, "fun 'n games", tomfoolery, not tension filled real life.
(Uh oh, the ultimate insult. She might as well have accused you of sleeping under bridges and sipping cheap wine from a paper bag.)
He: "My pleasure, princess. Your smile lights up the night sky. May I present my humble self, a paragon among geeks, the vaunted virtuoso of vapid vainglorious vaudeville, a knight of the Noble Order of Pocket Protectors?"