#you'll've

You should generally avoid using double contractions—at least in formal writing. Contractions of any kind are generally frowned upon in formal writing, so you can bet that double contractions are twice as bad.

If you were to use double contractions in conversations, we doubt that anyone would correct you. For instance, if you said, “I’d’ve (I would have) gotten that question right,” none of your friends are likely to point out that you shouldn’t have used a double contraction.

However, your professor, teacher, or editor will definitely criticize you if you use “you’ll’ve (you will have)” in an essay. Some of them—rightly or wrongly—even take points off for common single contractions such as “it’s,” “I’m,” and “they’re.”

You don’t even save that much time by using double contractions. According to our extremely nonscientific research,

“I would have” = 2.01214 seconds to type ⏲

“I’d’ve” = 2.01212 seconds to type ⏲

💁 Saving a whopping 0.00002 seconds and incurring the wrath of a teacher in the process is just not worth the pain.

What an interesting question.

The short answer is no—at least in formal writing. Contractions of any kind are generally frowned upon in formal writing, so you can bet that double contractions are doubly disapproved.

If you were to use double contractions in conversations, we doubt that anyone would correct you. For instance, if you said, "I'd've (I would have) gotten that question right," none of your friends are likely to point out that you shouldn't have used a double contraction.

However, your professor, teacher, or editor will definitely criticize you if you use "you'll've (you will have)" in an essay. Some of them—rightly or wrongly—even take points off for legitimate contractions such as "it's," "I'm," and "they're."

So take our advice and don't use double contractions. There really is no need to do so. (Avoiding having to type a few extra letters doesn't save that much time anyway.)

Cheers.