A Midlife Widow’s Search for Love

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widow's search for love

Listen to this episode of Last First Date Radio with Debbie Weiss, as she reveals a midlife widow’s search for love

Debbie Weiss is the author of Available As Is: A Midlife Widow’s Search for Love. A former lawyer, she has essays published in the New York Times’ Modern Love column among other places. She’s proudest of getting an MFA at 56. She lives in Benicia, CA with her second life partner, Randal.

In this episode of Last First Date Radio:

  • How she began a widow’s search for love after loss
  • What it was like to start dating as a 50 year old widow who hadn’t dated since she was 16
  • The biggest problem with dating over 50
  • How she met her second life partner

EP 553: Debbie Weiss – A Midlife Widow’s Search for Love

What made you decide to start dating after your loss?

I was lonely and wanted to find love again. I had never dated before meeting my husband. I wanted a serious commitment, a true partner. I also wanted to pursue my passions – yoga, writing, travel. I wanted to maintain my friendships and have my own life.


What was it like to start dating as a 50-year-old widow when you hadn’t dated since you were 16?

I went on JDate. It wasn’t great, because there wasn’t a huge pool near where I live. Most of the men had ‘mommy issues’ and I don’t have a lot of sympathy for that, because I lost my mom when I was young.

I tried the apps and OkCupid. I liked OkCupid more, because there was more information on the men, and it was easier to choose.


How did you find Randal, your second life partner?

I met him on OkCupid. I wasn’t meeting anyone for a while. I had a picture on my dating site with Vans with skulls on them. He messaged me asking me where he could get those shoes, and that’s how we started dating. We first met for tea. I had just had my worst breakup ever. He was sad about the loss of his mother. So, we started as friends. After a while, he invited me on a day trip, and it was wonderful. That was our first romantic date. We just moved in together, and it’s been great!


Tell me about your book.

It’s about creating a new life after being widowed. It’s about finding a voice after an all-encompassing marriage. He controlled the bills and finances. He did home improvement projects. I had to learn how to find my own thing. I write about dating and grieving. I wanted to offer hope and humor.


What are your final words of advice for anyone who wants to go on their last first date?

Find yourself first. Dating can have a lot of negative energy, so feel secure within yourself. There are a lot of good people, but there are also those who aren’t. Stand up for yourself and cut people loose if they are not right for you.


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