Man Falls For Best Friend's Sister
DEAR HARRIETTE: My best friend and I have been practically brothers for the past 15 years. Being that close, I have spent a lot of time with his family (and vice versa), and in that time, his sister and I have grown fond of each other. We text sometimes and talk about activities and places we should explore together, but out of respect for my best friend, her older brother, I've avoided taking the leap into romance. We flirt when we're around each other but try our best -- at least I do -- to keep it to a minimum. It feels like a crush that has gone on for far too long.
I finally worked up the courage to tell my best friend, and he said that he does not want me pursuing his sister. I made the mistake of framing it as a question as opposed to a statement simply informing him of my feelings and intentions. Now I'm stuck between defying my best friend's "wishes" and pursuing someone I have real feelings for. Is this long-standing love interest worth risking a 15-year brotherhood? -- I Love Her
DEAR I LOVE HER: This is a tough one, but if you truly feel like you love his sister, it could be worth what will be (hopefully) temporary discomfort. Speak to her first. Tell her that you have feelings for her. Check in to see where her heart is. If she seems interested in you, let her know that her brother does not approve, but you are willing to fight for the chance to explore a relationship if she is up for it. Since her brother will likely be hostile toward both of you -- at least at first -- it is important for you both to be ready. Otherwise, you could sneak around, but that behavior would make it less likely that a healthy relationship could blossom. Be strong and honest about your intentions.
Tell your friend that you love him, but you have grown to love his sister, too. Out of respect for him, you wanted to tell him, but you aren't asking for permission; instead, you hope you've earned his blessing.
DEAR HARRIETTE: I've been seriously considering moving out of the country, but I keep hesitating because it feels like such a drastic decision. I worry about how my friends and family will react and whether they'll understand why I'd want to leave. At the same time, I can't ignore this persistent feeling pulling me toward a specific country. It's been on my mind for quite a while now, and I feel both excited and curious about what life there could look like. I'm torn between staying where things are familiar and following this unknown path that keeps calling me. What does this feeling mean, and how do I know if it's something I should pursue? -- Out of the Country
DEAR OUT OF THE COUNTRY: Guess what? An international move doesn't have to mean forever. Plenty of people explore the world, stay in touch with family and find happiness. You can, too. If you are available to make the move, now is a perfect time to see the world.
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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 to askharriette@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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