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Sure, but given situations in which it could not respond, it could elicit elaboration. From that point on, it would be able to handle increasingly sophisticated responses to that specific situation. It's a data aggregation problem, similar to what we experience, as humans.

I also question exactly how unique individual elements of our lives are. In aggregate, they are probably fairly unique, but at an elemental level, we're all probably fairly mundane.

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Also, your hypothetical program is not static. It can communicate with thousands of other humans in real time. To half the user base it is Samantha, to the other half, it is Sam. If someone asks Samantha a personal question it doesn't know how to answer, it may try to pose a similar question to the other users as Sam. The larger the user base, the faster and more effective this can become.

It won't be as fast as a real human, but with some clever stalling techniques, it might be able to pull it of realistically.

In reality, if someone pulled a program like this off, it wouldn't just be Sam and Samantha. It would be thousands of different personalities, trying to build a realistic social network between its own personalities and between its human users. It would be like a mirror held up to society itself.

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