A mother wrote to the shadchan in the “Flatbush Jewish Journal,” about being annoyed that the boy her daughter was dating a few times, was going to E”Y for Chanukah. She wanted to know if they had a right to be upset with him, and I think basically she was saying she felt he had no business going on a trip while dating her daughter, and wanted to know should they be concerned about him.
It is perfectly acceptable to ask if they should be concerned about him. Many times people see warning signs and ignore them because they don’t trust their own intuition.
If they are used to getting engaged after 5-6 dates, and they already had 3, then the question is a good one. It may after all not be a concern at all, but to ask the question is definitely a good choice. It is not called pushiness to get advice during your child’s dating process.