Is She a Picky Single Woman?

By Amy Dickinson | February 9th, 2024

Or is she simply wise and discerning?

Beautiful picky single woman outside in a field of flowers. Image by Annanahabed

After a decade of being single, a woman wonders if she’s become too finicky. See what Ask Amy advises this picky single woman.

Dear Amy:

I’m a 50-year-old woman, and I haven’t had a serious relationship in about a decade. My first two partners (when I was in my 20s and early 30s) were controlling and emotionally abusive.

I know I overlooked a lot of obvious red flags back then (and made excuses for these people).

So, now, if there’s the slightest sign of jerkiness early on – if he teases me (a “just kidding” insult), corrects me (especially if he’s wrong), is rude to me or others, or bad mouths his exes – I usually won’t see the guy again.

I also balk when guys come on too strong in the beginning.

And that means I rarely go past the second or third date.

Am I being too careful? I’m worried I’ve become too thin-skinned.

– Worried and Alone

Dear Worried:

Every characteristic you mention: “Just kidding” insults, corrections, rudeness, badmouthing, coming on too strong – is a justified dealbreaker, at least from where I sit.

You might work on your reaction to being “corrected,” but being mansplained or corrected by someone who is not only wrong but rude about it is another matter. (You could examine whether you become defensive when others disagree with you.)

But let’s say that you really have become thin-skinned.

So what? This is you. Maybe you’re extra-discerning. Being too hard on people is not a good thing, but discernment is.

Upon meeting a stranger for a potential relationship, your instincts are all you have.

My main suggestion is that you should work on relaxing. Not relaxing your standards, but just … relaxing.

Many people fumble their first meetings – they might drink too much, misread the room, or simply be nervous. Maybe your guard is up a little high, and his guard isn’t up high enough. That’s why second dates were invented.

Even very discerning people can learn something new by cultivating an attitude of openness, but this doesn’t mean you should overlook a person’s behavior, especially when that behavior is rude or unkind.

Dearly departed Maya Angelou gave the world a finely cut gem of advice when she said, “When someone shows you who they are, believe them the first time.”

Want to get even more life tips from Amy? Read more of her advice columns here!

In the tradition of the great personal advice columnists, Chicago Tribune’s Amy Dickinson is a plainspoken straight shooter who relates to readers of all ages. She answers personal questions by addressing issues from both her head and her heart – ranging from a picky single woman to dark family secrets and DNA surprises. A solid reporter, Dickinson researches her topics to provide readers with informed opinions and answers. You can email Amy Dickinson at or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068.

©2024 by Amy Dickinson

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