Why Tom Needs a Break

On Life and Love after 50 eNewsletter
March 13, 2026
by Columnist Tom Blake
Last Friday, the eNewsletter featured Debbie in an Ask The Therapist article about the importance of communication for couples. I was surprised that so many men responded, albeit briefly. Here are four comments from men. 

An Orange County man stated, “Debbie’s article was very helpful for me. I know I need to talk some things out with my lady friend, but I don’t speak up because I want to keep the peace. Timing is important too. The way I communicate is key as well. Thanks, Debbie, for your help.” 

Wayne emailed, “Debbie, “You were a great pinch hitter…excellent column. Thank you.” 

Bill, “I liked your insight and smooth writing. Thank you for this very important and timely message.”  

Terry, aka, the funny plumber, simply asked, “Tom, Are you okay?” He was responding to Debbie’s opening comment, which was: “Tom asked if I would write another episode of Ask the Therapist. He needed a bit of a respite after everything that has been going on in his life…”

Tom’s response to Terry “I’m fine, Terry, but I needed (and still do) a break. Please understand I’m not complaining—no whoa-is-me type of stuff. 

“As many of you know, for 13 months, I’ve been trying to sell a property I’ve owned in Palm Springs for eight years. That meant lots of improvements and work projects. The property went into escrow three times and fell out. The real estate market in Palm Springs has been difficult. One of the reasons is that the Canadiens are avoiding renting or purchasing real estate out there.

They have always been a big part of the snowbird visitors and property owners. They aren’t traveling to the USA much these days. “So, there have been many time-consuming trips out there and back to Orange County. Thankfully, the property sold in late February. But all furniture that had not been sold or disposed of was shipped home via professional movers to my Dana Point home. 

“And lately, I’m working on preparing my tax returns for 2025. I know that sounds silly, as we all need to do that, but with two properties (Palm Springs was a rental) I got a bit behind in my tax record-keeping. Hopefully, I will finish that challenge this week. 

“Plus, writing this eNewsletter weekly and my newspaper columns bi-weekly takes several hours each week. The publisher of those three papers does not permit me to write what I’ve written in my weekly eNewsletters. 

“Also, taking time was a four-day trip to San Francisco to meet up with old Victoria Station Restaurant chain buddies as we attended a special Johnny Cash tribute concert at the Bohemian Club on February 26, with 400 male club members in attendance. 

“The night of the concert, my buddies told a club member that I had known Johnny Cash. The man asked if I had read Johnny’s Man In Black autobiography (see photo above). I told him I had an autographed copy of the book at home. “When I returned home, I looked at the book and saw that Johnny’s autographed message to me was signed on August 15, 1975.The book had been published on August 1, 1975, so my copy was likely one of the first of that book that Johnny signed. Thirteen million copies of that book have been sold. “

So, enough about me and why Debbie said I needed a rest. As we age, we all need to take a break occasionally. To keep the eNewsletter chugging along, we need your questions, stories, and comments. Let me hear from you.

Cheri said, “I have a question referencing background checks… whom do I contact and how long does this take…I would appreciate your response asap…I love your articles and hope you’re well.” 

Background checks. That’s an important topic for next week. Share your experiences and which company you would recommend.

A Journey of Love and Lessons Learned

On Life and Love after 50 eNewsletter
March 28, 2025
By Columnist Tom Blake
Like many seniors, I wasn’t prepared for dating later in life. My journey began in 1993, when my third wife (6 years), with no prior discussions or warning, moved out of my house. Two months later, she filed for divorce, leaving me to navigate the dating scene—a frustrating endeavor. 

Online dating wasn’t an option back then. Fortunately, I owned Tutor and Spunky’s, a popular deli in Dana Point, California, where many appealing women walked through the deli door. However, most were significantly younger and had no interest in a recently divorced man in his mid-50s. 

Struggling with the dating scene, I started a blog to document my experiences. That blog inspired my first newspaper column, published on July 7, 1994, titled, Home Alone With Only Dogs For Company.

Five years later, in my deli, an attractive, soft-spoken woman about my age with a kind and gentle disposition ordered a freshly squeezed carrot juice. While she waited for her juice, I walked over to her and asked her on a date. She said, “Yes, that would be lovely.” That started a 25-year relationship with Greta. 

Though we never married, we lived together for 22 years, first in her San Clemente home, then in my Dana Point abode. She was a Special Education teacher. We travelled the world when we took time off from work.

Greta passed away on October 29, 2022. I was one lost puppy. Technically, I wasn’t a widower, but the pain and grief were the same. After months of loneliness, I decided to reenter the dating scene.

Without the deli as a dating hub, I sought other ways to connect with people. I attended a grief support group, which proved invaluable. Not only did it help me realize I wasn’t alone in my struggles, but it also introduced me to new friends—both men and women—whom I still socialize with today.

To any single senior, I highly recommend joining social groups as a way to build meaningful connections. I was aware that the dating landscape had changed dramatically over 25 years, with online dating emerging as a dominant force.

Aware of its pitfalls, I recognized that online dating also provided an opportunity to meet people beyond my immediate geographical area. With that in mind, I joined online sites Zoosk and Match.com. Despite hearing from some women that “All the good men are taken,” I remained optimistic.

Yes, I encountered scammers and dishonest individuals, but I also met wonderful women. Patience—never my strongest trait—was essential. After messaging Debbie for a few weeks, she finally messaged me back and agreed to meet.

She is 10 years younger and lives in Mission Viejo, about a half hour drive from my home in Dana Point. We began dating in May of 2023 and shared many interests. She worked as a self-employed psychotherapist and had two daughters and two grandchildren, living in other cities. Though we came from different religious backgrounds, we connected over our shared love of sports—she’s a Kansas Jayhawks fan, while I root for the Michigan Wolverines, our respective alma maters. 

We also shared a love of music. She attended junior high and high school on Long Island (New York) with Billy Joel. And in the 1970s, I worked with and became friends with Johnny Cash. 

Like any relationship, we’ve had our ups and downs, but we’ve learned to compromise and adjust—essential lessons for seniors in new relationships. We see each other three to four times a week, balancing companionship with personal space. She enjoys her time with friends, and I do the same. She also visits her family. As we approach two years together, chemistry remains. Senior dating has unique challenges, and I feel fortunate to have found Debbie.

Our journey reminds me that love and companionship are possible at any stage in life—if one remains open to the possibilities. Please send me your stories, questions, and comments.
Ask The Therapist

You may be wondering what happened to the Ask The Therapist section. There have been so many questions to Debbie (yes, that Debbie, my significant other) about senior sex that I’ve decided to have her comments about that be the entire eNewsletter next week. So tune in.

Also, a woman Champ reached out to Debbie for personal help. The woman contacted me and thanked me, saying Debbie has helped her immensely.