Dear Dr. Date,
Here is an interesting situation and I am curious as to how you think it could be pursued. In one of my classes there are two sisters that both look very beautiful. I have talked to them on occasion but not at length. The problem is that they are usually both together and I do not see how I can ask one on a date (either one) without the other being right there (which could be very rude in a way). How would you go about doing this? Your advice is greatly appreciated.
— Curious

Isn’t this what Cinemax is all about? As I recall, there is a show called the” Red Shoe Diaries” that caters to this sort of fantasy. The show is similar to “Love American Style” in that there is different erotic tale each week told to this mysterious sexual investigator (played by David Duchovny no less) in the form of a confessional letter. He walks around empty warehouses and muses poetically about lust and love to his dog.
Speaking of dogs, there is a fable that may be of help here. A dog with a bone in his mouth walks proudly across a bridge. In the middle, he looks over the side of the bridge and sees another dog with a bone. He becomes enraged or jealous or something and growls at the other dog to give him the bone. The other dog just growls back. Slighted, our dog makes his fateful mistake by barking at the other dog, who, of course, is only his own reflection. When he opens his mouth, the bone falls out and into the river, lost forever. Now our poor pup has nothing! Of course, he forgot about it in about two minutes and started chasing some birds, but this might really hound you.
You see, your problem is you don’t really want to ask just one of them out. You want to date or get with both of them, don’t you? It would be all the more triumphant and amazing if you could date (or sleep with) both of them at the same time. Depending on your personality, you may or may not want them each to know about it. Regardless of your intricate fantasies, I’m going to shock everyone by giving you an atypical Dr. Date answer: Go for it!
It’s not too often that you are presented with the opportunity to date sisters. From the sound of it, you feel you’ve got a legitimate shot at pulling it off, so don’t let me stop you. There are a few rules you should conscientiously abide by, however. First, don’t lie to them. Second, don’t split them up or damage their special relationship. And last, don’t forget about the ultimate achievement — dating their mother, too.