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Man Plays Coy After Years Of Flirting

Harriette Cole on

DEAR HARRIETTE: There's a guy who's constantly liking and responding to my posts on social media -- I'm talking for two years and counting! A few years back, he was married to someone I'm only a few degrees separated from. I didn't know the woman, but I'm friendly with her sister. So even when they divorced and he started complimenting me on social media, I remained cautious; I would like his messages but never respond with my own. Over the past year or so, work functions have had us cross paths in person more often, and he's piqued my curiosity with his charisma and gentle aura. I decided to message him and ask if he'd like to have a drink with me. He said he'll let me know if he's available. I feel totally blown off and confused. Why was he constantly sending messages and flirtatious emojis just to reject me? Any ideas? -- Not Interested

DEAR NOT INTERESTED: I wonder if he is curious as to why you never responded to his overtures before. Could he think you have blown him off or at least that you aren't interested in him? Don't give up yet. See if he responds in the coming days. If you continue to think you could like him, write to him one more time. Be direct: Say you've noticed that he has been commenting on your page for a long time. Would he like to have a real conversation? See what happens.

DEAR HARRIETTE: My sister and I have a complicated relationship. We're adults, but I'm still trying to navigate our bond. Sometimes she treats me like I'm her best friend and other times she treats me like she can do away with me, as if hanging out with me is a burden. It weighs on me, but I really haven't addressed it with her.

Lately, some of my close friends have taken it upon themselves to invite my sister to their birthdays, graduations, family events and other celebrations, and it makes me uneasy. Is it OK to ask my friends not to do that? I want to tell my friends that their decisions to befriend her makes my relationship with her feel more complicated, but it also feels strange to tell other adults who they can and can't be friends with. Am I misplacing my frustrations? -- Family & Friends

DEAR FAMILY & FRIENDS: Your issue is with your sister. Don't amplify it by bringing in your friends. Muster up the courage to talk to her directly. Ask her why she runs hot and cold with you. Point out that this is a pattern that you have noticed, and it makes you uncomfortable. Try not to be confrontational as you want her to open up and talk to you. You want to understand why she does the things she does -- and you want her to stop.

Point out that you are both adults now. Old behaviors do not have to follow you into adulthood. Ask her to treat you with respect.

 

You can also bring up your friends. Say that it's kind of them to include her in their activities, but when she is acting dismissive of you, it feels awkward. You don't want her negativity spilling over to your friends.

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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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