Harriette Cole: I haven’t told him, but I’m on his girlfriend’s side

DEAR HARRIETTE: My roommate and his girlfriend constantly bicker, and I always end up being dragged into the middle of their arguments.

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Harriette Cole: How can I tell my friend I dread our conversations?

It’s frustrating because I feel like I’m being forced to pick sides when I don’t even want to be involved at all.

To make matters worse, I can’t help but feel bad for his girlfriend because, frankly, my roommate is wrong most of the time. He’s selfish, dismissive of her feelings and stingy when it comes to sharing expenses or treating her to a nice date.

I can tell she’s unhappy with how he treats her, but for some reason, she stays with him.

The other day, my roommate came to me asking for advice about their relationship, and I felt conflicted. On one hand, I want to be honest with him and tell him he’s the problem, but I also don’t want to ruin our friendship by being too blunt.

I’ve always tried to stay neutral, and I made a rule for myself not to give people advice about their relationships because it never ends well, but now I feel trapped because I know he’s in the wrong. I feel bad enabling his behavior by saying nothing.

Should I stay out of it and abide by my rule, or should I tell him the truth, even if it risks our friendship?

— In the Middle

DEAR IN THE MIDDLE: Do your roommate a solid and talk to him openly.

Tell him that you have worked hard to stay out of his relationship as you know it’s none of your business, but since he has repeatedly asked you for advice, you have one thing to offer: You believe that he could treat his girlfriend better. Your observations are that he could be more thoughtful, more generous and kinder.

He may appreciate your candor. He may not have had positive role models to help guide him toward loving, supportive behavior, so your insight may prove helpful to him.

Tread lightly, though, and be gentle. You are right not to want to be in the middle of his drama.

DEAR HARRIETTE: I am a college professor, and I’ve noticed that one of my students has been struggling significantly in my class.

At first, I thought it might just be an issue with the material, but after observing their behavior and performance, I have a strong feeling that it’s tied to factors outside of the classroom. This student, who was once engaged and consistent, has started turning in late assignments, missing classes and appearing distracted when they are present.

I’ve tried reaching out casually during class breaks or after lectures, but they seem reluctant to open up.

I don’t want to pry too much or make them uncomfortable, but I feel responsible for creating a supportive environment where they feel comfortable seeking help if they need it.

As a professor, I’m unsure how far I should go in addressing this. I want to help, but I also don’t want to overstep my boundaries or assume too much about their personal life.

Should I continue trying to approach them, or should I step back and let them come to me if they’re ready?

— Student in Need

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DEAR STUDENT IN NEED: Try one more time by inviting the student to office hours. Ask how things are going. Express that this student’s patterns have changed, and you noticed and wanted to check in.

Inquire if there is anything you can do to support them at this time. Offer to listen if they want to talk. Remind them that your door is always open.

Your department head or dean may have additional insight regarding campus services that might benefit this troubled student.

Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to askharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.

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