Meeting Too Many Disagreeable Men on Dates

A divorced 52-year-old woman kept encountering disagreeable men on dates and wrote “Ask Amy” for advice. More than a year later, advice columnist Amy Dickinson followed up with the writer to see if the advice worked.

Dear Readers:

Like you, I’m often curious about what happens to the advice I offer once it leaves my desk, and so I’ve asked readers to send in “updates” to let all of us know how my advice was received, if it was followed, and how things turned out.

The responses have flowed in, and I’m interested and often gratified to learn what impact this experience has had on readers.

This year I celebrate my 20th year of writing this column. Publishing these updates reminds me that we have been through a lot over these past decades. Some of these updates read like postcards from old friends, and I’m happy to share them.

To refresh all of our memories, I’m running the original Q&A, followed by the update.

Dear Amy:

I am a divorced 52-year-old woman who is experiencing a disturbing situation. Men I meet for possible relationships have what I describe as argumentative personalities.

They are never agreeable with any topics that come up in conversation. The topics range from personal decisions to politics to differences between men and women. These men come across as misogynistic, condescending, critical of everything around them, yet they see themselves as decent, normal, good guys who know how to treat women. They couldn’t be more wrong.

They often present topics that are inflammatory and then say women can’t handle the conversations because we are too caught up in our feelings.

I don’t entertain these disagreeable men for long, but I meet man after man after man that have these same personalities.

Just what has happened to the art of decent conversation?

After talking to these men for a short period of time the focus turns away from seeking companionship to sparring partners. I don’t understand it and it is very frustrating. Amy, just what is this phenomenon?

– Missing the Art of Conversation

Dear Missing:

At the risk of being accused of misandry, let’s state for the record that men undoubtedly also have a laundry list of gender-based frustrations with the women they are meeting.

If you are having the same sort of experience over and over again, you should take a careful look at whatever (presumably online) venue you are using to meet these disagreeable men, and see if there are red flags in their profiles that might indicate that they are more interested in sparring than sparking.

During my long-ago journey into online matching, I admit to having experiences similar to yours. It seemed that the people I was meeting were sometimes relitigating their previous relationships. I often felt unduly challenged and tested. Honestly, few of these people seemed actually interested in getting to know me at all.

This might be a function of the speed with which many people approach the matching process. Match, meet, test for compatibility, move on. And the anonymity of social media has transformed some people into conversational jackals.

My take is this: Engaging in a peaceful and informative conversation has always been something of a rarity (yes, it’s an art!). Being with someone who listens with interest, who seems to “see” you, and who can challenge you without raising your hackles — these are qualities you enjoy in your deep and intimate friendships. This is what you’re looking for, and so your best bet might be to move off-line and to join groups and organizations where you can meet and get to know people gradually, IRL (in real life).

(Published in December 2022)

Update from “Missing” on disagreeable men:

Dear Amy,

I accepted your advice of moving offline – where I was meeting most of these men – and put myself where I could encounter people IRL (in real life).

I found that when I made eye contact and smiled at people in groups and social situations it did start the process of conversation, especially with men.

When the conversation has turned to an inflammatory topic, I’ve said, “That doesn’t really interest me at all; perhaps you can find someone else to talk to about that.”

Also, I still follow a bit of advice you published years ago.

You wrote: “People who are decent and kind get to share my world. Everyone else can take a seat.”

I found this on an index card I had in an old journal. It is now posted where I can always see it.

– Not Missing the Art of Conversation Anymore

Dear Not Missing:

I’ve heard of columns being taped to refrigerators, but I’m honored to have made it onto your index card!

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 disagreeable men 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 askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068.

©2023 by Amy Dickinson