Woman Dating Friend's Former One-Night Stand
DEAR HARRIETTE: I just found out my friend is dating a guy I slept with a couple of years ago back in college. None of my friends knew; it was a one-night stand, and I was too ashamed to tell them a secret that I thought would never resurface. Now, two years later, one of my best friends is seriously dating the guy. They've been going steady for a few months now. My friend and I live states away and don't catch up as often as we should, which is why I'm only just finding out. I don't believe they've been intimate yet, but I wonder if I should be honest with my friend about the night I shared with this guy. Would I be ruining something good with old, irrelevant news? Or would my friend genuinely want to know?
The other factor that keeps gnawing at me is that he knows of our friendship. Now, he could have grown genuine feelings for my friend, but I feel a little uneasy that he would pursue the friend of someone he's already slept with. I'm not sure how to proceed. If you were in this situation, would you tell your best friend? -- Love Triangle
DEAR LOVE TRIANGLE: I'm guessing that if what you had with this guy was only a one-night stand, it doesn't mean anything to either of you. I hate to say it, but there is even a chance that he may not remember. That said, you called her one of your best friends. I don't think you should hide it from her, nor make it a big deal. Tell her you went out with him once and whatever your impression was. If he seemed like a nice guy, say so. If she wants to know more, spill the beans: It was a one-night stand, and a one-night stand only. There it is, on the table. She will have the information. You will have been transparent, and it shouldn't be a big deal.
DEAR HARRIETTE: I'm starting to take something personally, and I don't know if I'm overreacting. Lately, whenever I start talking to someone new -- whether it's a potential date or even just a new connection -- it seems to fizzle out almost immediately. We might exchange a few texts or have a short phone call, but then they either stop responding or cancel plans altogether. Over the course of a year, this has happened four or five times -- enough that I'm beginning to wonder if the problem is me. Am I coming across as boring? Am I saying something that turns people off without realizing it? I try to be engaging and genuine, but now I find myself overthinking every interaction. It's discouraging and honestly a bit embarrassing. How can I figure out what I might be doing wrong and rebuild my confidence in the process? -- Losing Interest
DEAR LOSING INTEREST: As disheartening as this seems, don't give up hope. You are making the effort to put yourself out there. Maybe put yourself in different places. The cliche of getting involved in activities that interest you where other people might go is actually a good idea. Enroll in a class. Join a gym. Go to museum and art openings. Put yourself in the company of people who share your interests. Then, boring won't be a part of the equation at all. Don't give up!
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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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