How do I / Should I, console a former classmate and stressed out PHD/MD applicant?
If you decide to reach out again, I would try to reconnect over a different topic first. It sounds like it has been a while since the results were announced, and bringing up their past disappointment over and over again will probably not help them get over it. If all of your interactions are focused on this one topic they might start to wonder if you are either secretly judging them about it, or if you are just pumping them for advice on what mistakes to avoid in your own applications.

If subsequently they bring up the topic on their own, you can express sympathy at that point. But I would follow their lead in whether they want to dwell on it or not.