Date Asks For Money After Getting Rejected
DEAR HARRIETTE: I recently went on a date with a man for drinks, and at first I thought I might be interested in seeing him again. We texted briefly after the date, but the more I reflected on our interaction, the more I realized he wasn't the type of man I want to be with. Initially, I planned to stop responding to his messages, but he continued texting me even after I stopped communicating with him. Because of that, I decided it was more respectful to be direct and let him know that I wasn't interested in continuing to see him. He responded by saying it was "all good," but then asked if I could send him money to pay him back for the drink he bought me on the date that he asked me out on. I was completely disgusted by his response. Instead of sending him the money, I chose to block him.
Now I'm second-guessing myself. Should I have just sent him the money to avoid the situation altogether, or was I right to stand my ground? As a result of this, I'm now wondering if dating is even worth it anymore. Should I continue putting myself out there in hopes of finding a man who is emotionally mature and respectful, or is it better to take a step back altogether? -- Bad Date
DEAR BAD DATE: You are not wrong to let your date know you don't want to continue going out with him. If he invited you on the date and paid for it, so be it -- you are not obliged to pay him back. Still, it's good to be aware of the cost of dating these days. Many are opting out of dating due to the expense. You have to weigh the pros and the cons.
In the world of apps and hookups and casual interactions, it can be hard to find someone you connect with. Don't give up, though. Perhaps change your strategy. I just talked to a couple who independently hired a matchmaker. This woman combed the entries she had collected and used her own knowledge and awareness to match them up. It worked. The couple just got married.
DEAR HARRIETTE: Before we took off for Christmas, a few of my colleagues gave me presents. I hadn't even thought of that and did not give them anything. Should I be following up with gifts for them even though it's after the fact? How do you handle a situation like this? I like them very much, but I have never given gifts to co-workers before for Christmas. -- No Gifts
DEAR NO GIFTS: Hopefully you thanked your colleagues in the moment. You can also reiterate your gratitude, if it feels appropriate. A New Year's gift wouldn't go wrong, but you don't want to make too big of a deal of it as that moment has passed. Next year, you might think of getting cards for your colleagues. Talk to a confidant to learn more about the unspoken culture of your company so that you can better fit in.
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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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