Reply To: Dating with a divorced guy – when should I ask about his divorce?

You should have found out from others at least partially before you agreed to meet him. A shadchen may or may not be honest. Your question whether you should bring it up yourself or wait for him to ask is worrisome. This is your life you’re talking about! If you’re always this timid, you need to see a therapist. I hope I’m not offending you by saying that. The forth date is certainly not too soon to ask. He shouldn’t mind your questions, and if he does it’s a giant red flag.