The one question I hate the most on a date is "How long have you been single?".
It's just a loaded question, full of the belief that we are in some way validated by the ability to get a boyfriend or girlfriend. Like a stamp of approval that you're good enough.
If you say a length of time that is deemed too long, there must be something wrong with you. What was it that stopped someone asking you, or why would you turn anyone down. It's at this point that some people try and justify the single life; I was too busy with my career; I'm fussy; I've not wanted to settle down etc. If you've been single, you must be defective.
If you say a length of time that is too short, you must be rebounding, or not ready to date probably again. It's hard to trust someone freshly wounded from a broken relationship too, how can they make any rational decision about dating again?
I've come to believe that most people want to hear somewhere between one to two years. I think people think that this length proves you're not rebounding, but that you're not a weirdo single, unable to snare someone in.
I tend to refuse to answer, just out of principle, unless of course I'm at that crucial 12-24 month window of course. Then I shout it from the rooftops.