Can you be supportive of a non listener?

BlackCat999
So, my question is simple, how do you react when you've seen something coming, try to warn someone, they decide to pursue despite and then fail?

I personally have a hard time empathising in these situations. I know this person and I consider them. Sadly they have the habit of not presenting themselves seriously, and not taking things that way either. I mean, even interviews for work. They tend to go with this "I don't care attitude".

The most recent example was an interview they passed to enter a school. They want to change work and going back to school is necessary since it has to do with taking charge of young prisoners/delinquents.

After the interview, they called and I ask how it went. From the tone of voice, the description of the interview and the reaction he said the interviewers had when he used certain words, I knew he blew his chances. Then he asked what I thought. He seemed happy of his performance and although no major incident happened in during the interviewer, I knew they didn't take him seriously. I understand for example, they asked him what he thought of filing legal documents and court proceedings and he said he doesn't like "paperwork" but already went to assist to court proceedings.

Coming from higher education, I know 100% that presentation and wording is extremely important in these situations. This person has a lot of ego and I definitely did my best to not be what he would call "negative" so... I hushed and told him I hope they accept him despite him insiting I went deeper, I knew this would blow up. I did try encouraging him to figure out a plan B just in case... Which he didn't do seriously too. So when he told me he failed, I honestly can say I wasn't surprised but, I can't tell him that...

Am I an ass? And how would you deal with this?
Can you be supportive of a non listener?
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