Mark: I couldn't apply to this University because I forgot about it. You: ... (Respond to Bad News).
I'm sorry to hear that. / That's too bad. / How disappointing. / You must be disappointed.
Sarah: I failed a very important exam. You: I'm sorry to hear that... (Offering to help).
If you want to talk, just call me. / If there's anything I can do, just let me know.
Judy: My boyfriend broke up with me. I'm so sad. You: That's too bad... (Offering to help).
If you want to talk, just call me. / If there's anything I can do, just let me know.