Compassionate listening can be a wonderful part of a cuddle session. Cuddling can also be a wonderful place to not have to talk and to enjoy comfortable silence with another. How much you talk and what you talk about is entirely up to the two of you.
Your practitioner is not a counselor or coach, and even if they are in other parts of their life, that is not part of a cuddle session. They will be happy to listen and be honest with you about how much is too much for them in terms of what you share. Everything is confidential unless you share any information of an illegal nature or the intention to do harm.