On Life and Love After 50 eNewsletter
February 23, 2024
By Columnist Thomas P Blake
In Senior Dating Difficult Choices Emerge
Fifteen years ago, a woman named Kathy attended a senior singles gathering at Tutor & Spunky’s, my Dana Point Deli. Her 42-year marriage had ended. She now lives on the East Coast, near her children. A while back, she wrote to tell me she had remarried, but was widowed just two years later.
Last week, Kathy emailed, “This past September I was called on two different Wednesdays to volunteer by answering the phones at my church office. At the end of each day, I went to supper where my church provides meals for those getting off work and others who are at church attending classes being offered.
“On both Wednesdays, I sat at the same table with friends from my Sunday School class. Each time the only chair available was next to John. On the second Wednesday, John shared how he would like me to be his friend. We even shook hands on it.
“Since then, our times together have involved eating out and going to activities or movies. We laugh a lot and he’s full of stories of his cowboy-roping days and places he lived growing up and helping his dad on oil riggs. All his stories have been interesting.
“I’ve enjoyed our friendship but have drawn back when he expressed that he really liked me. I’ve reminded him that we are just friends. Based on my history, I’m a bit vulnerable and protective of getting too involved in a relationship.
“His age (80) and his health are drawbacks to me.
“When I mentioned his age to my cousin, she, aware that I am 76, said with a smirk, ‘And how old are you? A four-year age difference is no big deal.’
“John’s a diabetic and he’s told me he has bone cancer. I’m finding that my suggestions on health have helped him in keeping his blood sugar down. He is open to my ideas and went to a good health store and is taking a protein drink, etc.
“This week he said that when he passes away, he wants me to have all his assets—including his house, car, and bank accounts. He went to a financial person to put it into action.
“He also stated if I would marry him, it would be simple as my name would be on all his things.
“You know me a little bit, Tom, and I’m not one to go jump on this and take advantage. I am praying for answers and looking also to my children who like John and want me to be happy.
“He wants to take a train trip out West. Time will tell.
“Your thoughts, Tom?”
Tom’s response to Kathy
“Kathy, the big lesson in your story, is that your meeting John shows when older singles get off the couch and out of the house and involved in activities (like senior volunteering) they enjoy, they improve their chances of meeting a potential mate.
“John sounds like a gentleman. He obviously cares a lot about you. You state that his age and health are holding you back. Aware of your past, I understand why you are hesitant.
“However, your cousin is right. Don’t let a four-year age difference stop you.
“Plus, when you meet someone with whom you are compatible–including attending the same church and sharing similar religious beliefs–consider yourself blessed.
“John’s health is an understandable concern. Diabetes can be controlled through a proper diet, medications, and lifestyle.
Bone cancer is of course a worry. Still, he could outlive you. It sounds like you’ve already helped him deal with his health issues, which he appreciates. Love each other now. Take that train trip out west.
“Regarding his estate. Does he have any children or other beneficiaries? He loves you and wants you to have his assets. What an incredible gesture. If he leaves you more than you need, you can pass that on to loved ones and the church you two share.
“Senior Marriage? Well, that’s up to you and John. He can still leave you his assets without tying the knot. Many seniors don’t want to marry again.”

