It happens to the best of men sooner or later. You’re dating a perfectly reasonable woman. She’s not bad in bed, she looks pretty hot when she’s made up to go out, and she’s decent company when you’re out for the evening. You think you’re doing just fine even if she’s not a model. Then she invites you over to her parent’s house for Boxing Day and you meet her sister.
It’s no contest. Her sister could be starring in a lingerie fashion show and you’ve just realized that you’re holding the runner’s up prize. Certainly you could choose to settle for what you have, but let’s be honest: there’s nothing to be gained by keeping that silver medal in your bed when gold could be in reach. It’s an operation that requires some care and some daring, but there’s no reason you can’t aim to bed her sister.
The first thing you must do is gather more information. Talk to your current girlfriend about her sister, but do it carefully. Odds are good she knows she’s the plain one in the family and she’s probably had men make passes at her sister before. Don’t let her know that you’re interested. Frame your questions as if they’re about her family dynamic or what her childhood was like. These questions will draw out information about her sister while appearing to be thoughtful questions about her. Keep an eye out for valuable information, especially if she refers to her sister as a slut or suggests she’s stolen boyfriends in the past.
If you’re lucky, her sister will be trying to bed you – either to spite her sister or because your charm at dinner was just that effective. If so, well done! Your job is half over already. Otherwise, you will have to plan your attack carefully. If they’re very close sisters and trust each other, your job is that much harder. The types of women who have close family bonds like that are often hopeless romantics, however, and you may have some luck throwing yourself at her door with a line about how you know it’s wrong but you couldn’t stop thinking about her.
The vast majority of sisters have a relationship of vaguely fond indifference and that makes your job a bit harder than it would be if she were a complete stranger. Find a way to spend some time with her. You might offer to do dishes or run an errand, and then tell your current girlfriend that she should relax and leave it to you. Now you will strike up a conversation with her sister, using all the same charms you would at the club.
She’ll let you know when you’ve pressed the right buttons, and soon enough you’ll have her pressing yours.