A womanizer generally considers himself to be both a ladies' man and a man's man, maintaining an atmosphere of mystique and sophistication. He may surround himself with other male players or a support posse, but he clearly exudes a superior level of self-confidence bordering on vanity and self-absorption.
While all of these trappings may help a womanizer seduce a new target, he is generally following a script which has proven to be successful in the past. Conversations are usually surface-level and tailored to appeal to the woman's personality and interests. A serial womanizer is keenly aware of how to hold a woman's interest through conversation and other seductions, which may work in his favor if he wants the date to escalate physically. This is all part of the seduction game for a chronic womanizer, who may not even be truly interested in the woman as an individual.
A habitual womanizer may have serious issues with women in general, which can be the hidden motivation behind the seduction and ultimate rejection process. A womanizer is often a male chauvinist who views women as inferiors or manipulators who somehow deserve to be played by an aggressive male. A womanizer may be so concerned about rejection that he makes sure he remains in complete control of every relationship he enters, no matter how superficial or fleeting. Some relationship experts suggest that a habitual womanizer may be reenacting a painful break-up experience every time he picks up a new "conquest."
Other womanizers may actually love the company of women too much. They cannot commit to an exclusive or monogamous relationship because there are far too many other interesting types of women to pursue. They don't necessarily want to hurt their current partners, but they also cannot resist the temptation to flirt with other women as assurance of their sexual or romantic prowess. A player or ladies' man may be very good at hiding his true nature from a long-term romantic partner, but eventually most womanizers either get caught in an infidelity or mature to the point where a monogamous relationship holds more appeal than serial seductions.
(ps Dedicate this to Mr.Pig)