{"id":2844,"date":"2026-06-23T09:06:28","date_gmt":"2026-06-23T09:06:28","guid":{"rendered":"https:\/\/nextcitydigest.com\/?p=2844"},"modified":"2026-06-23T09:06:28","modified_gmt":"2026-06-23T09:06:28","slug":"harriette-cole-i-made-the-mistake-of-asking-if-i-could-date-his-sister","status":"publish","type":"post","link":"https:\/\/nextcitydigest.com\/?p=2844","title":{"rendered":"Harriette Cole: I made the mistake of asking if I could date his sister"},"content":{"rendered":"
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DEAR HARRIETTE<\/strong>: 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.<\/p>\n

Read more Miss Manners: There\u2019s no drinking at my fireworks party<\/a><\/p>\n

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\u2019ve avoided taking the leap into romance. We flirt when we\u2019re around each other but try our best \u2014 at least I do \u2014 to keep it to a minimum. It feels like a crush that has gone on for far too long.<\/p>\n

I finally worked up the courage to tell my best friend, and he said that he does not want me pursuing his sister.<\/p>\n

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\u2019m stuck between defying my best friend\u2019s \u201cwishes\u201d and pursuing someone I have real feelings for.<\/p>\n

Is this long-standing love interest worth risking a 15-year brotherhood?<\/p>\n

\u2014 I Love Her<\/em><\/p>\n

DEAR I LOVE HER<\/strong>: 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.<\/p>\n

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.<\/p>\n

\n<\/div>\n

Since her brother will likely be hostile toward both of you \u2014 at least at first \u2014 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.<\/p>\n

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\u2019t asking for permission; instead, you hope you\u2019ve earned his blessing.<\/p>\n

Read more Today in History: June 23, Thai soccer team gets trapped in flooded cave<\/a><\/p>\n

DEAR HARRIETTE<\/strong>: I\u2019ve been seriously considering moving out of the country, but I keep hesitating because it feels like such a drastic decision.<\/p>\n

I worry about how my friends and family will react and whether they\u2019ll understand why I\u2019d want to leave.<\/p>\n

\n<\/div>\n

At the same time, I can\u2019t ignore this persistent feeling pulling me toward a specific country. It\u2019s been on my mind for quite a while now, and I feel both excited and curious about what life there could look like.<\/p>\n

I\u2019m 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\u2019s something I should pursue?<\/p>\n

\u2014 Out of the Country<\/em><\/p>\n

DEAR OUT OF THE COUNTRY:<\/strong> Guess what? An international move doesn\u2019t have to mean forever. Plenty of people explore the world, stay in touch with family and find happiness. You can, too.<\/p>\n

If you are available to make the move, now is a perfect time to see the world.<\/p>\n

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.<\/em><\/p>\n

Read more Here\u2019s how to see hundreds of live music concerts for free in Bay Area<\/a><\/p>\n<\/div>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

Now that he has said no, is it worth risking our friendship?<\/p>\n","protected":false},"author":1,"featured_media":92,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[6],"tags":[],"class_list":["post-2844","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-advice"],"yoast_head":"\nHarriette Cole: I made the mistake of asking if I could date his sister - Next City Digest<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/nextcitydigest.com\/?p=2844\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Harriette Cole: I made the mistake of asking if I could date his sister - Next City Digest\" \/>\n<meta property=\"og:description\" content=\"Now that he has said no, is it worth risking our friendship?\" \/>\n<meta property=\"og:url\" content=\"https:\/\/nextcitydigest.com\/?p=2844\" \/>\n<meta property=\"og:site_name\" content=\"Next City Digest\" \/>\n<meta property=\"article:published_time\" content=\"2026-06-23T09:06:28+00:00\" \/>\n<meta name=\"author\" content=\"admin\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"admin\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"3 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/nextcitydigest.com\\\/?p=2844#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/nextcitydigest.com\\\/?p=2844\"},\"author\":{\"name\":\"admin\",\"@id\":\"https:\\\/\\\/nextcitydigest.com\\\/#\\\/schema\\\/person\\\/13065d40d633843429ac57d4e5c06f9b\"},\"headline\":\"Harriette Cole: I made the mistake of asking if I could date his sister\",\"datePublished\":\"2026-06-23T09:06:28+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/nextcitydigest.com\\\/?p=2844\"},\"wordCount\":635,\"commentCount\":0,\"image\":{\"@id\":\"https:\\\/\\\/nextcitydigest.com\\\/?p=2844#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/nextcitydigest.com\\\/wp-content\\\/uploads\\\/2026\\\/05\\\/0139233f8c854ca253912d1b9432926f.webp\",\"articleSection\":[\"Advice\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/nextcitydigest.com\\\/?p=2844#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/nextcitydigest.com\\\/?p=2844\",\"url\":\"https:\\\/\\\/nextcitydigest.com\\\/?p=2844\",\"name\":\"Harriette Cole: I made the mistake of asking if I could date his sister - 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