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I know someone that dropped out of college after one year and I think it is pretty sad. I was thinking about talking to him about it. I am currently in college and have been for about 3 years. I was wondering if talking about it could encourage him to go again. Specifically, I was wondering if I should ask him if he misses going to college. The last time he came over here he seemed sad for some reason. I wondered if the fact that I live on a college campus had something to do with it. Like it reminded him of the opportunity he missed out on. But I don't want to make him feel uncomfortable or like a failure.
 

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Specifically, I was wondering if I should ask him if he misses going to college.
I don't see why not. If he doesn't want to talk about it, he can change the subject or just say he'd rather not discuss it. But there's no harm in bringing it up in the first place, and I think "do you miss going to college" is a pretty good way of bringing it up.
 
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