Debbie Weiss – Medium

Featured Book

Available As Is: A Midlife Widow's Search for Love

Available As Is: A Midlife Widow's Search for Love

A sudden widow at fifty, Debbie Weiss captures the absurdity of modern dating as a grown up. Offering unexpected humor and much-welcome hope.

2022

Stories

Pinned

Debbie Weiss
in
P.S. I Love You

Disillusionment: It’s What’s Killing Middle-Aged Dating

Let’s try treating our dates as potential life partners instead of bottom feeders

6 min readNov 24, 2020

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Disillusionment: It’s What’s Killing Middle-Aged Dating

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Debbie Weiss
in
P.S. I Love You

On Dating at Middle Age: Where are All the Grown-Up Men?

Or Why Do So Few Guys Clean Out their Refrigerators?

6 min readFeb 20, 2021

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145

On Dating at Middle Age: Where are All the Grown-Up Men?

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145

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Debbie Weiss
in
P.S. I Love You

The Biggest Problem with Middle-Aged Dating? Living in the Past.

When I started dating after losing my husband, my biggest surprise was that everyone was disillusioned. Dating was exercise in revenge.

5 min readApr 30, 2020

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The Biggest Problem with Middle-Aged Dating? Living in the Past.

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Debbie Weiss
in
P.S. I Love You

The One-Upmanship that is Middle-Aged Dating

Why Love Shouldn’t be like Working at a Law Firm

5 min readJan 22, 2021

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35

Womand fencing and holding a sword

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Debbie Weiss
in
Crow’s Feet

What We’ve Lost in the Workplace

I used to think I was a professional failure, until I realized I’d been set up to fail.

6 min readMay 28, 2023

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What We’ve Lost in the Workplace

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Debbie Weiss
in
Heart Affairs

Date Like a Lawyer

How to Take no Prisoners when Love becomes Litigation.

6 min readApr 6, 2023

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9

Two people in blazers and glasses staring each other down

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Debbie Weiss

At almost 60, I am a lawyer and homeowner.

1 min readMar 18, 2023

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Debbie Weiss
in
Heart Affairs

Do People Over 50 Fall in Love?

I had no idea dating at midlife would be such a power struggle.

6 min readMar 12, 2023

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68

Do People Over 50 Fall in Love?

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Debbie Weiss
in
P.S. I Love You

Abandoning Dating at Middle Age in Favor of Friendship

Or Time for the Lysistrata Method

6 min readJun 10, 2021

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Abandoning Dating at Middle Age in Favor of Friendship

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Debbie Weiss
in
P.S. I Love You

Overcoming the Bitterness that is Middle-Aged Dating

Or I never tried to convince a guy to clean out my roof gutters.

5 min readApr 5, 2021

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Overcoming the Bitterness that is Middle-Aged Dating

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Debbie Weiss

Debbie Weiss

Book Author

Author of award-winning book “Available As Is: A Midlife Widow’s Search for Love.” Essays in Huff Po, the New York Times’ Modern Love and others.

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