Advice
Need advice?
Have a weird question? Wondering what to do? Can't make a decision? Do you need to know if it's YOU or them?
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As a former preschool teacher, nanny and child educator, I have learned a lot about babies, toddlers and kids. I also worked in project management, insurance and more. I have an obsession with science; archaeology, Egyptology, space travel and much more.
Originally from the east coast, I have experienced many parts of the USA which are so beautiful. I am a forward, blunt and honest person. No subject or topic is off the table, but politics should be avoided to maintain peace. (unless it has to do with your question.)
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Subject: Advice
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Just Ask!
We've all been there, we need feedback from an outside source. Maybe to process, or to hear it, but I encourage you to ask.
(Let me know in the email if you want to remain anonymous.)
Which fork do I use first? Can I put my elbow on the table? What do I do if I burp at a fancy dinner? And so much more!
I grew up in New Canaan, CT and I learned how to act in certain situations. This skill has vastly helped me to network and blend in anywhere I go, no matter how fancy it may be. Grow your knowledge and confidence, becoming a classy gentleman or woman.
AITA?
Share your scenario and I will do my best to let you know if it's you, or them. Be ready though, I am brutally honest!
AITA = Am I the A-hole? These are usually lengthy descriptions of a situation where the writer asks for feedback. WIBTA also permitted (Would I be the A-hole)
Question of the week:
June 22, 2026
Dear Holly,
I have three roommates and we all share rent and bills equally. We all work and we get along as much as needed to cohabitate. However, one of our female roommates (three ladies, one guy), is very free with her body and is not modest. She is clearly not self conscious at all and wears thong panties and other, skimpy not-outfits around the house.
We’re all adults, we can avert our eyes but when none of us ever do this, should we ask her to cover up more? Is it wrong to ask? We three have talked about this and cannot agree on what we should do, or if we should do anything at all. We don’t want to make her uncomfortable at all, but she is making us three very uncomfortable.
One of the ladies has already put in notice and is moving out, just to get away from it. We truly don’t know what, if anything, to do.
Besides the skimpy clothing issue, she’s a great roommate; keeps her area clean, doesn’t leave messes for others, adds food for everyone etc., but how is she so unaware with this one thing?
Please help,
Brad, Lauren and Hailee.
Answer will be posted after 06/25/2026.
See post on Facebook for more:
https://www.facebook.com/share/p/14pEzGKQXP4/
Best wishes,
Holly
Weekly Question - Past Editions
Dear Holly,
"I am a classic 'people pleaser.' I always say yes to extra tasks, favors, and events, and now I'm completely exhausted. Where do I even start with setting boundaries?"
-Anonymous
June 17, 2026 EDITION
Dear Anonymous,
This is tricky, and I completely understand where you're coming from. What you’re feeling is incredibly common; thousands of people struggle with advocating for themselves, setting boundaries, and especially enforcing them.
Here’s what helped me: I started practicing saying “no” as a daily goal, and I offered zero explanations. It was almost physically painful at first. I felt awkward, uncomfortable, and guilty as I walked away. It sucked.But then something shifted. People adjusted, as long as I held my ground. You may need to remind someone of your boundary once, but only once. After that, if they continue pushing, it’s intentional or it’s rude.
A good way to gauge fairness is this: Would I do the same or ask the same of them? If the answer is an instant “no,” then the behavior is no longer acceptable for you.
For example:“Holly, would you please stay late and help me finish my presentation?”
Do not apologize when establishing a boundary. You’re not doing anything wrong.
"I can’t stay today. I’m sure you’ll figure it out though - you’re amazing at this!” Then leave. Quickly.
If they push: “Why not?” Give them a calm, steady look and maintain eye contact. You: “Because it’s your work, not mine. Have a great night.” Then leave. Or: “Because I’m off at five, which is now.”
Use whatever version feels most natural to you. You don’t owe anyone an explanation, including your boss. After five o’clock, they’re not your boss, they’re just annoying. Best of luck as you move through the discomfort. You can do this, and you’ll be so proud of yourself!
Best wishes,
Holly