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I think it's a very tricky question, because it might be difficult for the therapist to come up with an answer that wouldn't disappoint in some way. What you (or any patient) may consider important/memorable to them, may not coincide with the therapist.
I can't imagine asking my therapist this. Because my memory can be poor and I'm not so good at threading things together chronologically, I've asked him what he remembers us talking about around x time in order to figure/work something out. But asking the question you ask, it just feels in the context of a completely different kind of relationship, not because of 'boundaries' just because it feels that way to me. And I feel like if I asked, he would feel uncomfortable, because he might feel that I was looking for a certain kind of answer, had certain expectations.
A memorable time for you may be making a card together, a memorable time for her (in terms of what's important to her as your therapist) may be an aha moment you had in therapy which helped you to move forward. I think it's a tricky question in that you are hoping for a certain kind of response, and the therapist, if they were honest and not trying to just tell you what you want to hear, may well disappoint in a way that would be painful.
Are you on some level (subconsciously) hoping for a certain kind of answer? For her to refer to something that was significant as far as the closeness of the relationship, rather than something more therapy-y?
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