The rake is basically a traditionalist when it comes to marriage. Not in the sense that he adheres to the marital bonds of constancy and fidelity, but more in the way that he demands a sizable dowry when taking his bride.
In order to secure such a sum, the rake must marshal every tool of deception in his arsenal, so asto fool the poor* bride-to-be and her family into thinking that he is an upstanding citizen of exceptional moral character. Which, of course, he is not. He should take every opportunity to speak to the girl's father of business matters and political happenings of national importance in order to impress upon him the appearance of a well connected and concerned citizen. On the other hand, he should subtly flirt with the mother of the bride, engendering a latent attraction in her, and increasing her desire for him to join the family.
Simpletons subscribe to the theory that impressing the father is of primary importance, and indeed it is the father who has the power to bestow or withhold the dot. However, the rake knows that every normal man's opinions, no matter how strong they may be, are ultimately ruled by his wife. Thus, having the mother on one's side is absolutely essential in securing a cushy fortune for the future. The same can be said about sisters. (N.B. Affairs with sisters should be kept discreet, for although they are extremely enjoyable, if the family catches wind of such an affaire de coeur, your chances for success will vanish as quickly as the first drink of the day.) Brothers are in fact your greatest enemies, as their natural protectiveness will lead to suspicion, and they might expose you for the fraud that you actually are. They should either be treated with indifference or chumminess, as the situation requires. You might consider setting up any single brothers with particularly talented former paramours, and so winning them over to your side. Also note that a close relationship with a beloved pet may work silent wonders in terms of your status in the family's eyes.
If, either through deliberate investigation or mere happenstance, the family catches wind of your true character, the hammer will almost immediately begin to drop. This is crisis mode. The solution is, with your most honeyed words and lying blandishments, to convince your fiancée to elope as soon as possible. Tell her that every moment that you spend not united to her in the bonds of holy matrimony is to you an aeon of agony. Tell her that you cannot imagine ever loving anyone in the world as much as you love her. Tell her anything--just make sure that she's at the nearest drive-thru chapel before any mention can be made of a pre-nuptial agreement. If this mad dash is successful, you can then divorce her immediately and recoup half of the marital assets, which will undoubtedly keep you living in style until your next sham of a marriage. Indeed, if properly executed, the only marriage that will be shorter and happier than yours is the glorious marriage of gin and vermouth known as a Martini.
However, if one is unable to elope and a pre-nuptial agreement is enforced, the rake must give a jurist's attention to the terms. **
In the worst-case scenario, you have already earned the family's opprobrium, and the girl refuses to elope. This is where prior preparation pays off. Over the entire duration of your engagement, you will naturally have been storing up as many family secrets and risqué private photographs of your fiance as possible. Store them with more care than pearls, as they are your last ticket to cash in on this courtship. Putting the bite on old dad generally doesn't pay as well as a dowry, but a bit of hush money can tide you over until you find the next unsuspecting target. It may be necessary to move to a different city, taking your secrets with you. For this reason, a rake never pursues his first marriage in the city that he would eventually like to inhabit.
* Please note that we mean poor in the unfortunate sense of the word (as in, unfortunately about to be jilted by you), not in the economic sense. A potential bride should never under any circumstances be economically poor.
** In a classic bluff, I once shocked a wealthy fiancée and her family by preemptively forcing her to sign a pre-nuptial agreement which included terms so strict that she became convinced of my "wealth." She not only was forced to maintain a certain BMI, but she even had to pay rent! She was so confused that she never got around to making me sign the document that her lawyers had prepared. You would be well-advised to take a page from my book.
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