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Harriette Cole: I keep replaying the moment this date went bad

May 27, 2025
Harriette Cole: I keep replaying the moment this date went bad

DEAR HARRIETTE: The other day, I was feeling spontaneous and decided to go on a date with someone I met recently. It felt like a big move for me because I was stepping out of my comfort zone.

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He was a little different from the type of person I usually go for, and I was proud of myself for being open-minded and giving it a shot.

At first, things seemed to be going OK, but toward the end of the night, he made an unprovoked, mean-spirited comment that completely caught me off guard. We ended up getting into an argument, and the date ended on a really sour note.

What he said was so unnecessarily hurtful that it’s been sitting with me for days, and now I can’t stop replaying the moment in my head.

I know it was just one bad date, but it honestly shook my confidence and made me wonder if dating is even worth it.

How do you move past something like this without letting it harden you or make you want to give up on dating altogether?

— Bad Date

DEAR BAD DATE: Unfortunately, bad dates occur. Please do not shut the door on the possibility that you might meet someone great at another time.

The good news is that you discovered on your first date with this person that his personality does not measure up to your expectations. Move on. Maybe the next person will be the one for you!

DEAR HARRIETTE: I’m a woman in my early 20s, just starting out in my career and trying to get my footing financially.

My older sister, who’s in her late 20s, recently accepted a new job in Missouri and is planning to move soon, but she doesn’t have the money to make it happen. Now my parents and sister are pressuring me to cover her moving costs, even though I live in Los Angeles (where everything is expensive) and don’t have a huge income myself.

They’re framing it like I should help because I’m “good with money” and live more independently than my sister. It feels unfair to be treated like the family bank just because I’m responsible.

I love my sister and want her to succeed, but I also feel resentful that I’m being put in this position, especially since she’s older than me and has had more time to get on her feet.

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How do I deal with this without damaging my relationship with my family or abandoning my own financial boundaries?

— Family Bank

DEAR FAMILY BANK: Suggest to your sister that she ask her new employer to cover her expenses — or at least some portion of them. She can tell them that she really wants to work for them but cannot afford the move without some financial help to get there.

Next, either tell her you cannot pay her expenses or agree to pay a portion that you can afford. Don’t feel forced to pay for her move. If your parents feel so strongly about helping your sister, they should chip in.

Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to [email protected] or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.

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