When the first reaction is to reassure the other it never is clear who is being reassured.
The person who is pointing out a problem.
Or the person who is reassuring the other that there is no problem.
What reassuring leaves out in such a case, is the opportunity to hear the pain.
And most often that is what reassuring is about. Avoiding any conversation about the existing pain as it is uncomfortable.
Sadly, whenever we let this opportunity out, the problem has the better chance to stay and reappear whenever a new occasion presents itself. But now the person remembers that they have not been listened to the last time.
Reassuring works, when the other person experiences, that his pain has been seen and felt.
It doesn’t work, whenever the conversation reappears or stays within a loop.
So it maybe is worth it, to invest that time checking in and have the person describe what it is that they are experiencing and what it is that they want. That will also take a few loops until it can be expressed, but the attitude is a different one. It shows the desire to listen.