Reader Wants To Help Classmate With Her Career
DEAR HARRIETTE: Recently, I presented a classmate of mine with an opportunity to step into her career. We were talking about career goals, and she mentioned she wanted to gain more experience. I knew of a low-stakes event that would allow building connections with industry professionals, so I shared as many details as I could and let her know I would be on the set if she felt overwhelmed. She didn't feel confident enough to go, but I think she would have done well. I don't want to be overly pushy; however, I do want her to know she can do her craft on the professional level.
We aren't super close, but she does appreciate the experience I have been able to gain over the years. How would you recommend I activate her talents, or is it not something I can influence? -- Nervous
DEAR NERVOUS: You are kind to want to help your classmate. Do a debrief with her about the event she missed from the perspective of what she might have been able to experience had she been there and why it would not have been scary. Suggest to her that next time she should just go for it. Attend the next function. Come early before it's crowded so she can get the lay of the land. If you can ever attend with her and support her, that would be great. Also, recognize that she is not your project. You can offer to help, but don't get caught up in her insecurities.
DEAR HARRIETTE: I have been with my boyfriend for five years, and he decided we should take a trip for our five-year anniversary. However, he wants to split things evenly when it comes to money. I would understand this if he couldn't financially pay for it, but he is a 38-year-old man who has more than enough extra income to pay for this trip on his own.
This situation has been weighing on me more than I expected. Over the course of our relationship, he has not consistently been the type to plan thoughtful gestures or go out of his way to make big romantic moves, and I think that's part of why this is bothering me so much. In my mind, a five-year anniversary feels like a big milestone, something worth celebrating in a meaningful and intentional way. Instead, the conversation quickly turned into logistics and splitting costs, which made it feel less romantic and more transactional. It left me feeling disappointed and, honestly, a little hurt. I haven't said much to him about how I feel because I don't want to come across as ungrateful or materialistic, but at the same time, I feel like this reflects on a larger issue in how he shows up in the relationship. How do I bring this up without it seeming like I'm a gold digger and bring more focus to how I feel respected in the relationship? -- Not on the Same Page
DEAR NOT ON THE SAME PAGE: At this five-year mark, sit down with your boyfriend and talk about goals and values. Tell him that his approach to the trip is bothering you. Reveal your concerns -- not that he should have to pay for everything, but that it would have been lovely had he offered. Tell him you love romantic gestures and thought this trip would be that, but it feels transactional. Ask him what he wants. Get each other to open up and really talk about your relationship and the future.
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(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions toaskharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)
Copyright 2026, Harriette Cole
COPYRIGHT 2026 Andrews McMeel Syndication. This feature may not be reproduced or distributed electronically, in print or otherwise without the written permission of Andrews McMeel Syndication.
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