What do you do when students feel guilty?

That's a question I asked my supervisor Joseph today. I don’t know if the words I say sounds accusing or if the way I say it sounds accusing or if just the topics of life I choose to talk about are more convicting but I hear I make people feel guilty.

There is history to this...
I once had a roommate, let's call her Bertha. I discipled her during her freshman year and then we became roommates. Everything was great until she really wanted to have a boyfriend. I tried to encourage her and pray with and for her but all she could think about was having a boyfriend. She became good friends with a very nice, non-yet-Christian man. She wanted to date him and I advised her that would not be a good idea with scripture and others' life experiences. Others in here live were encouraging her to date him and eventually she did. I told her I didn't think it was a good idea again but continued checking in with her and the spiritual health of the relationship and her own health as a friend but not again telling her to stop dating him. Yet after a few months she stopped talking to me about him and would avoid any question I asked about him. She eventually broke up with him, met a nice Christian man and got married. I asked what happened to our friendship and she said she felt guilty, or that I wanted her to feel guilty all the time.

I realized the way I communicate things can come off judgmental if not followed up with love-if others can't see that it comes from love and not care and concern. At the same time though I wondered if it was her own guilt imposed on herself because, after I realized she would continue to date him, I just wanted to love her anyway. I didn't judge her I advised her and loved her and she felt guilty. Much later she admitted that she should never have been dating a non-Christian...

I wonder...
Is there good guilt and bad guilt? Does a guilt trip mean one person is manipulating the other? Or can someone really feel guilt because they are struggling with it internally and would rather think it was brought on by an outsider?

Currently...
I learned how I say things makes a difference and that how I approach a topic and with what love I portray all makes a difference in how what I say is received.

Today I praised the FT Bible study saying they had great connections with many students in the dorms because the leaders were spending them there, and I think that's really cool! The other leader I was with said, "Thanks for making us feel guilty."
Halt. That statement was to praise FT and the great things I saw-not directed at any other leader to make them feel guilty. Perhaps they would be encouraged to hear of the great things happening in FT and want that to happen in their own study but not feel guilty about anything. We talked about it a little more but the leader maintained "some people would take that as guilt."

By chance does that mean that my leader feels guilty about not spending more time in the dorms? By seeing the great things done by others are they jealous? What did I say wrong? I shall ask them that when we're alone and feel it out more but really,
What do you do when students feel guilty?