On a first or second date one will typically be asked when was the last time you were in a relationship. There are really only a few answers to give and ways to give said answers.
–if you got your heartbroken recently, then simply say “I had a not so fun break-up a few months ago but I learned so much from it and am ready to have fun again.”
–if you just got out of a long relationship, then reply “I was with someone for awhile but in the end we realized we wanted different things.”
–if you haven’t been in a relationship in more than a year, then say “it’s been a while and I’ve been meeting lots of nice people but no one that I’ve wanted to take it to the next level with.”
Leave it at one line, using some kind of variation of the above depending upon your circumstance. If and when this date becomes a relationship then you can exchange stories and delve deeper, but for the first few dates it’s not worth it. A longer explanation will only put a damper on the date. If you have to ask the question then at least preempt it with “I don’t want to know the details right now, but I was wondering when the last relationship you were in was?” and if you’re asked the question first then you will need to ask it in return whether you want to or not because it’s the polite thing to do. Then move on to another topic.