Some things are genuinely different. Others are not, and treating them as different is its own obstacle.
What is actually different
You know more. You have seen what a marriage requires day to day. That is real knowledge and most first-time daters do not have it.
Your tolerance for vagueness is lower. Usually an advantage. People dating after divorce tend to ask the real questions sooner and end things faster, which saves everyone time.
There may be children. This changes the logistics of dating and the substance of any serious conversation. It also changes the timeline — introducing someone to children is a decision with consequences beyond the two of you.
There is an ongoing relationship with an ex. If there are children, that relationship continues permanently. A future partner is marrying into it.
The pool is different. Older, more likely to have been married, more likely to have children. That is not a worse pool — in some respects it is a considerably more grown-up one.
What is not different
You are not damaged goods and you are not starting from behind. Divorce is common in every Jewish community, including observant ones. Anyone who treats it as disqualifying has told you something useful about themselves.
And the things that make a marriage work are the same as they ever were: kindness, reliability, the ability to repair, and wanting the same life.
Where halachah comes in
One point of substance. Under traditional halachah, a get — a Jewish bill of divorce — is required in addition to a civil divorce before a remarriage is recognised. Its absence has serious consequences under Jewish law, and it can prevent a religious remarriage entirely.
This is a genuine halachic question, the process differs between communities, and there are situations — including where one party refuses — that require real rabbinic and sometimes legal help.
If you were married Jewishly, speak to a rabbi about a get before you are engaged again, not during wedding planning. If a get is being withheld, there are organisations and rabbinic authorities that work specifically on this; it is not something to carry alone.
Before you start
Can you describe what happened without it taking over? Not without feeling — without it becoming the subject. If every conversation returns there, that is a readiness signal.
Do you know your own part? Not accepting all the blame, and not assigning it all. Someone who can say what they would do differently is in a much better position than someone whose account is entirely about the other person.
What does your week actually look like? If there are children, be honest about the time available. Dating on the two evenings a fortnight you have is possible, and it requires someone who understands that.
What do you want that you did not have? This question produces more useful answers after a marriage than before one.
The Dating Readiness tool looks specifically at recovery from the past alongside clarity, capacity and resilience, and it is worth five minutes before you start rather than four months in.
Telling someone
Early, briefly, without an essay. “I was married for nine years, we divorced three years ago, we have two children who are with me most of the time” is enough for a first or second date. The detail comes later, if it goes somewhere.
What you are watching for is how they receive it. Someone visibly recalculating is telling you something worth knowing now.
And be equally interested in their history. Someone who has never been married at forty has a story too, and it is not automatically a simpler one.
See also: Jewish matchmaking when you already have children.