On January 10, 2025, the eNewsletter was titled, “False Hope.” It was about a Champ named Ann, not her true name, who wrote that she had met a man named Ben (name changed also) whose wife had had Alzheimer’s Disease for 10 years.Ben’s wife still lived at home under his care. On Christmas Day, 2024, Ben contacted Ann and they met for a glass of wine that day and found they were attracted to each other, especially Ann attracted to Ben.
Ann emailed me often in early 2025 about her encounters with Ben. On May 26, 2025, Ann emailed me, “I heard from Ben on Mother’s Day, remember him with the Alzheimer wife? He lovingly wished me happy Mother’s Day and, of course, I was over the moon.
The next eNewsletter, January 17, 2025 (Both eNewsletters can be read on my FindingLoveAfter50.com website, featured 22 responses from Champs about the brief encounter Ann had with Ben. Almost all responses felt Ben was cheating on his wife and Ann was totally out of line.
“I thanked him and said I thought of him and hoped he was well. He also texted me on Easter, this coming from a man who wanted the door closed. I responded.
Last week, she emailed again.
“I have no idea how his wife is doing, apparently, she’s still here and things might be the same. I think you know how I feel about Ben; he is still the one for me.”
“Then, in the evening he responded to my text and said he also thought of me and here comes the next thing that sent me shivers, he said maybe someday we can go out for dinner.
Ann emailed me several times in 2025 and early 2026, always writing about Ben.
“I have been seeing Ben, I believe I wrote you after he bailed again but I did not follow up with what happened after. The next day, after the breakup, he texted me, it was heartbreaking to read how he poured out his heart.
“He said he didn’t know what had come over him, that life was so stressful with his wife still alive, but lovingly taken care every day and night.
“Ben said he had deep feelings for me and didn’t want to lose me, could I please forgive him and could we talk. We did and got some things straightened out; I felt more understanding as this continues to be a difficult situation for us both.
“Ben tries hard to include me in his life; he has a very busy business plus he visits his wife (living separately in their home) a couple of times a day.
“He obviously loves her and makes sure she has every comfort possible; I love that about him as well as other things. You know Tom, I have loved Ben for over a year, and I believe he had strong feelings about me and decided last Christmas to visit me again.
“Tom, there is never a guarantee in life, not for me, not for you or anyone for that matter.
“I believe I told you about our reunion, we just flew into each other’s arms after 10 months and almost cried with joy. He had that little one-day setback but promised to never hurt me again.
“Ben has been loving and considerate since, we have gone out to dinner, to lunch and we see each other once a week, sometimes like this week, twice for lunch.
“We visit each other’s homes, and I feel comfortable in his house. He holds my hand during lunch, kisses me frequently and thinks I am eye candy, a cute expression he uses.
“As I mentioned, it’s not ideal, I want to see more of him but know the limits, don’t want to push it and let him talk about his pain, (his wife and both daughters he lost a few years ago).
“It now has been almost three months of being together, I know he loves me and I am loving him.
“I am older now, it feels right to be with Ben and one day, we can spend more time together once his wife is no longer with us. I am grateful for this love.”
On Life and Love after 50 eNewsletter March 27, 2026 By Columnist Tom Blake
A Remarkable Woman Champ
I’ve often stated that Champs amaze me. This week’s Champ story adds to that feeling. Here’s why.
An email arrived in my inbox a week ago on Wednesday, March 18, 2026. The woman requested I not use her true name, so, I will call her Molly. It read, “Thank you, Tom, for honoring a promise you made to me. If you think it might lighten Jack’s burden, please do let him read my post.” (I didn’t recall that I had made a promise to Molly almost three years ago).
Molly continued, “At present, I’ve gotten older (96 years old), and lost all family and most friends. It’s a very lonely life. I’ve moved to a lovely condo by the beach. Trying to make some more friends. “Tell Jack there are many more women out there, better, more caring, and lonely too.
“Jack should have learned a lot by now about how to protect himself against money-hungry women. There are also money-hungry men. I would never ask anyone to sign anything.
“Before my fiancé passed, he wanted to leave all of his estate to me. I refused it. I didn’t want it. But I had no choice. He saw a lawyer without me knowing. And left me some things. I’ve treasured them. “I’m so sorry, Jack got tangled up with that woman.
“If I can help in any way, please let me know. Maybe my talking with Jack could help relieve his burden.”
I was beyond perplexed by Molly’s email. I had no idea who Molly was or what she was talking about. Not a clue. What promise did I make to her and when? How did I honor that promise?I didn’t know we had a 96-year-old Champ, and who the hell was the Jack she referred to?
On my Gmail account, I used the email search tool that archives previous emails and typed in Molly’s email address, which appeared in her March 16, 2026, email. The article was about Jack (not his real name), a Champ, who had made several dating mistakes when he was involved in a long-term, living-together, non-marriage relationship.
“There were a lot of financial mistakes made along the way, as well as others, but the most egregious one was his believing she would be there for him, “for richer, for poorer, and in sickness and health.”
“When Jack became seriously ill, and ended up in the hospital for a week, two weeks later she bolted! Jack was devastated. It was this scenario that Molly wanted to address. Now, almost three years later, she wrote to say that if her story would help to lighten Jack’s burden, I could now share it.
The mystery started to unravel. My Gmail archive showed that Molly had sent me an email on Jul 21, 2023, at 9:04 p.m. Earlier that day, I had published an eNewsletter titled “Love is Blind. A Senior Man Ignored Relationship Warning Signals.”
The topic was mainly about a Champ named Jack, whose relationship blunders affected his relationship. Plus, I included some details of my third marriage, in which I made relationship mistakes as well.
Molly’s July 21, 2023, email stated:
“I read your eNewsletter today and thought to myself, it could have happened to me. I’m sorry that happened to both you and Jack.
“Years ago, I lost my husband of 45 years to pancreatic cancer. We had a good marriage.
“After that, I met a psychologist recommended by my friend in New York while visiting her. She asked him to come over to help me with the loss. He stopped by and was very kind and quite intelligent.Spoke with me for hours. I had to return to California after being away for a few weeks. He kept in touch with me daily. He helped a lot. Stopped my crying and depression. This treatment went on for months.
“He mentioned how bad the ice and snow were in upstate NY. I invited him to come to sunny CA. He accepted. We got more acquainted. He told me he would never marry again. He had two very bad marriages.
“He decided he liked me and asked if we could get closer. I wasn’t quite ready. He would wait. After a few more months, he asked again. He suggested we live in NY for the summers, and spend winters in CA.
“This went on for years. We had many differences. He was a Democrat; I became a Republican. Small stuff. But then he wanted to get married. I didn’t. He got Alzheimer’s. I told him that I would help in every way possible if he could move here; I would take good care of him. We had been together for 16 years by that time. His family wanted no part of him.
“I went back to NY and helped him dispose of everything that wasn’t necessary. Brought him back to live here with me. Within a year, he got much worse. He had to be in a nursing home full-time. I had promised I would take care of him, and I kept my word because I truly cared for him. He passed away after another three years. I went to the nursing home every day.
“I took care of the burial; his family didn’t even want to talk with him when they could’ve. It broke my heart watching him decline. I’m thankful for knowing him for over twenty years.
“How anyone could just walk out on anyone sick and needy is a sin on their soul.
“Please don’t publish this email. I just felt you and your friend Jack should realize there are honest, dependable and loving women around. You must look at them with open eyes, before getting too involved.”
I emailed Molly back that same 2023 day. I wrote, “Thank you, Molly. A very touching story. You are an angel. I will honor your wishes and not publish your story.”
Checking the archives answered my questions listed above about why Molly emailed me last week. Yes, this Champ amazes me. She’s 96 and is willing to reach out now to a man I wrote about nearly three years ago. What a wonderful gesture
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.
On Life and Love after 50 eNewsletter February 20, 2026 By Columnist Tom Blake
Today’s On Life and Love After 50 eNewsletter was inspired by comments from Champs, particularly by Carolyn, who said, “I absolutely and unequivocally loved reading last week’s beautiful Valentine’s Day eNewsletter! So much fun to read all about Yoko’s exciting trip to Japan and eating the black eggs. Thanks to her for the fascinating photo of the black eggs! I also loved seeing the Hello Kitty train! Yay!
“I love anything related to Valentine’s Day! I attended a beautiful Valentine’s Day Party with lots of dancing and dinner! Had a fabulous time! I suspect that you and Debbie had an amazing and beautiful Valentine’s Day.
Tom’s comment. Since Carolyn mentioned that Debbie’s and my Valentine’s Day together was likely amazing and beautiful, I will expound on it.
A better definition of our day would be unusual. Most of you know that I have been trying to sell my Palm Springs vacation home for a year. It’s been a difficult challenge. It fell out of escrow three times. It has been in escrow a fourth time, and it looks like this time it will sell (hopefully). For those of you who have sold properties recently, you know that a big and challenging part of the process is getting rid of furniture and precious belongings, unless you’re able to sell “as is”.
Debbie has been a big help in that regard. She has posted items online for sale and dealt with people seeking low-price deals. Some of the large and heavy furniture pieces were a special challenge. She and I spent much of January and early February in Palm Springs as the hoped-for sale neared. There were a few items that either she or I wanted in our Orange County homes. We hired movers who picked those items up on Thursday, February 12. The truck was crammed full. Plus, we each had driven our own automobiles to Palm Springs and loaded each car with the remaining items that didn’t fit in the mover’s truck.
Sadly, there were six items that wouldn’t fit in our cars. We were going to have to leave them behind. We thought our realtor, Maureen, might store them in her garage until we could make another trip out there, but we knew that was asking a lot of her. And I was not up for another trip to Palm Springs, at least not for another week.
The moving truck left at 11 a.m. with a first stop at Debbie’s place in Mission Viejo. She drove separately to her home in her car, loaded with items. I drove away shortly thereafter, a little sad and emotional, realizing that an enjoyable eight-year period of my Palm Springs life was ending, and arrived in Dana Point around 1:30 p.m. The moving truck arrived at 8:30 p.m. and left about 9:30. I was exhausted. My garage was full.
The next morning, Friday, the 13th, Debbie called and said she had planned to drive back to Palm Springs that day to pick up the six items, but she had injured her ankle with all the lifting and movement, so she was going to drive out on Valentine’s Day instead to try to load the remaining items in her car. I didn’t want her to do that on Valentine’s Day by herself (or any day, for that matter), and I knew those six items would not all fit in her car. So, I drove the two of us in my Honda SUV, which had more room, on Valentine’s Day to Palm Springs and back, which took seven hours.
We were both exhausted, but we laughed at how the two of us seniors were spending our romantic Valentine’s Day. The remaining six pieces fit in my car, but a large clay pot was on the floor of her passenger seat, so her knees were crunched up and bent the whole way back. Now the romantic part of our Valentine’s Day: a lunch together on our return trip to the coast.
We stopped at the Morongo Casino gas station off the I-10 freeway to fill the tank ($1 a gallon cheaper vs other gas stations). An IN-N-OUT Burger restaurant was 50 yards away from the gas pumps. We splurged with a romantic lunch. Debbie had a grilled cheese sandwich; I had a cheeseburger. We split an order of fries and a small diet Coke.
So, Carolyn, our “amazing and beautiful” Valentine’s Day didn’t quite fit that description, but it was memorable, a day we won’t forget.
More Champ CommentsMK (a woman), “As usual, I enjoyed your eclectic column.You do a great service by offering a venue for people to share their stories. I’m happy for you that your selling ordeal is nearly over. Tom’s response, “I’m still waiting for the final phone call to hear that the Palm Springs home has been sold and I hope it’s within 3-4 days.”
Pony Lady, “I loved all the comments about Valentine’s Day. It’s interesting how people feel differently about it.”
Lynn, Santa Margarita, CA, “Thanks for last week’s lovely eNewsletter. WELL, DONE! I did a bit of an early Valentine’s gift for myself. On Feb 5, I wanted a happy-color for my jump-into-my-first-hybrid car. I call her honeybee! Her 600 miles per 11.9-gallon tank is hard to beat! Thanks for all your newsletters…they are so fun & eye opening! “We all really do make our own happiness, making fun where’s there’s none is my mantra! Wishing you a GREAT WEEKEND!”
Tom’s response, “Beautiful car–way to go! “While not new, I call my 2013 Honda CRV Leo.” And often thank him for getting me safely to places. Lynn’s naming her car spawned an unusual topic for next week’s eNewsletter; even a little strange, a little weird, but kind of cute. After all, we older seniors need things that entertain us and keep us happy.
So, Champs, if you still drive a car or own a car, do you name your car, and if so, what name, year, and type of car? Why did you pick that name? Please let me know.
Two women with decidedly different outlooks on senior life
Helen
Helen emailed, “Single woman fear of dating. I need some assistance; okay, I need help. I am 71, and the monster under my bed is dating. I live in fear of dating. My last real date was in 1981. I’ve been a widow for 10 years. I tried a couple of coffee/lunch dates and had no success. I was knocked off the horse, and I just can’t seem to get back in the saddle. I’m not that young, cute girl. I lost my confidence, and I am afraid to try again. Yes, I’m chicken.
“I want a second chance, but I have convinced myself it will be a disaster. I am not the perfect older woman these men seem to be searching for. At the grocery store, I would be on the dented can aisle.
“I am all too knowledgeable about my issues. I lean on those instead of my good qualities. I think the pain of widowhood has taken away my confidence and left me feeling like failure is my only route.
“I have lots of good qualities. I’m clever, creative, intelligent, funny, and likable. I’m kind, caring, and loving. I put others first, I’m a good listener, and I know I’m still a keeper. But in the back of my head, I think of my flaws and my age. I consider myself a used car and not a classic. And I don’t want to disappoint anyone.
“I injured my ankle, so I can’t compete in pickleball. And I’m not a hardbody, but my sons say I’m still cute. I know I don’t look my age or act it either because I’m young at heart, and I’m reminded about this by strangers. I just need a kick in the butt. I need to polish up my courage and spirit.
“So, Tom, I need to pick your brain, hit up your knowledge and hope you have ideas for me.”
Tom’s comment: With all the good qualities you describe, I don’t understand your fear. You’re young, and it doesn’t matter that you can’t play pickleball. With my bony knees, I can’t either. I strongly suggest you contact a therapist to overcome your fears.
Maria
Some Champs have told me they are bored in retirement. They don’t know what to do. One Champ named Maria messaged me this week with how she is enjoying retirement and getting exercise at the same time.
I’ve known her for many years. She was my dental hygienist. Now, she has started a new business. The brochure below explains her new adventure.
Maria lives in Ironwood, near Ranco Cucamonga and Ontario, in Riverside County, California, just north of the 10 freeway. She is open to servicing customers within 25 miles of her home.
She is a reliable and wonderful woman. Trust her to take care of your dogs.
Last week, we shared widower Bill’s jitters about a first date he had with Jackie, a woman he met online. Here are 14 responses I selected, plus my comments at the end.
George, “I’m a little surprised that Bill didn’t mention what kind of full-time work Jackie does. It’s 1/3 of her daily life – it includes successes and other accomplishments, challenges and stresses. Does she have any kids and/or grandchildren? What is her family life like? Whom does she associate with and what do those people do?
“Her responses would have helped bring her out and see what the two of them have in common. Bill is a widower – does he have any kids? Do their kids have something in common?”
Kaitte, “I totally agree with Bill. Everything Jackie did sends red flags to me. This guy is a real gentleman. Send him my way to Colorado. LOL. It’s a long way away.”
Victoria, “I’d say she paid whether he knew it or not. What a waste of her time!”
S (a woman), “Jackie’s not interested. I wouldn’t exactly fall all over in gratitude for a sandwich and drink either. He sees himself spending money and it’s not going anywhere. What exactly does that mean? Where other than forward does he want to go? It’s called courting, Bill.”
Carolyn, “Oh, Oh! I don’t think Jackie is interested In seeing Bill again. He sounds like a nice guy to know and hike with. It is possible because she is still working so she doesn’t find him compatible.
“I’m happy that Bill spoke to you first about that upcoming date. You gave him excellent advice. Please let him know that he did everything right. This was just not a good connection for Jackie.
“However, I always say, ‘Keep hope alive!’ Tell him to continue to seek a woman who is interested in him. He’s a good guy to know.”
Pat, “Bill did nothing wrong and is a gentleman. Her response was lukewarm, and he should draw the line there and accept no more of that treatment. He should send a brief text thanking her for her company, since he said he would, and leave it at that. She’s a grownup and can initiate if she wants to. He doesn’t need to bend over backwards because he’s busy looking for a woman who is willing.
“She didn’t ask questions because she was dealing with what was in front of her. Maybe she wanted someone who exhibited signs of wealth so she could stop working.
“Maybe she wanted someone 60 because she believes that she looks 60 and maybe she does. None of that is Bill’s problem and he shouldn’t take it personally. He should keep looking and expect it will take effort. Lots of ladies reading this wish they could walk on the beach with him. He sounds like a keeper.
“As to ‘Who Pays for the senior date?” it’s not about what’s fair, counting pennies, women’s lib, what he expects in return, yada yada. Here’s the truth: That is how he SHOWS how he FEELS about her, and if he wants to see her again. And it only needs to be a small appropriate amount. If he doesn’t pay a small tab she will think he didn’t really like her. Enjoying a drink together is a nice gesture and it gives you something to do with your hands!”
Virginia, “Wow, I always enjoy reading your articles. Being a senior but very active and fit, I too am looking for a partner. Not wanting to get married again, but I would love to hang out, cook, and dance. Listen to music and go on hikes together.
“I must tell you the story about the gentleman that I went out with over Christmas time we went out a couple of times, and then I invited him over for dinner.
“He seemed to enjoy the dinner and afterwards I was clearing the table, and he disappeared, I went into the living room, and he had fallen asleep on my sofa! Wow, I was shocked. Maybe I wasn’t a very good conversationalist. Who knows? When he woke up, he said. “Oh gosh, I fell asleep,” and, I said, “Oh gosh, maybe it’s time for you to leave.”
Gloria, “That first date does not sound too encouraging. Jackie steered away from any plans and that may say a lot. On the other hand, she might be shy and afraid to show too much interest; we don’t know about her past experiences.
“Bill is unsure what to do, which is understandable because he got little feedback. That is discouraging. I think the only thing to do is ask her for another date. Texting Jackie might be the safest way.
“If Jackie responds with a no thank you then Bill knows and can let it go.
But maybe she says yes, and they can proceed from there. Good luck Bill, keep your fingers crossed.”
Jeanne, “Jackie definitely was not interested. I could feel her vibes. I usually let the man know by thanking him and wishing him luck in his search. I let him know that I enjoyed him but didn’t feel we were a match. A kind let down is better than leaving him guessing. Many of my dating friends felt that was the wrong way to do it and I always felt it was right for me. I guess I’m not a people pleaser!”
Marie, “Bill, Jackie doesn’t seem to want to pursue a friendship with you. Trying to win her would require a lot of time and energy spent on your part with no result. You seem to be a nice gentleman. You will find your person soon.”
Belinda, “Wow. What Bill wrote, ‘I see myself spending money on dinners and maybe going nowhere’, really tells all. He’s more concerned with his wallet than he is with her! A breakfast sandwich and a beverage has him concerned? And the next date ideas were a walk or a hike…
“As a 64-year-old attractive eligible woman of some means, the way he acted on this date screams CHEAP to me. I would’ve been turned off, too. These men need to understand that especially in the early phases of dating, they can’t act overly concerned about their budget on a date. IT’S A TOTAL TURNOFF to a woman.
“We want to feel valued and respected and even put on a little bit of a pedestal early on, especially if we are just getting to know you. What we DON’T WANT is some guy giving us vibes that maybe the potential connection isn’t worth a breakfast sandwich with a beverage, or some ‘dinners that go nowhere.’
“I would’ve been cold, too. Sorry, but this guy needs to improve his mindset, so this cheap attitude doesn’t bleed through on dates.”
Gail, “Jackie is not interested in any future dates with Bill.”
Laurie, “I’m flabbergasted. That gentleman was trying to be nice, I get it. Good, he’s trying.
“But the wishy-washy waffling, ‘Ghost her then text?’ What kind of crap is that?
“She hasn’t made up her mind yet! Give her time to digest the date. She’s got a lot going on, and this is supposed to be pleasant for both people. This guy sounds high maintenance to me.”
Christine, Relationship expert, “Dating is so hard for both sides. Sadly, no one knows what to do. Even though most people seem to think ‘They should just know how to date and feel stupid that they don’t.’
“Everyone wants the other person to ‘go first.’ Say they want to do something again. Say they liked them or (even) didn’t like them.
“So, my advice to everyone is to say the truth nicely.
“If you enjoyed the conversation and would like to do it again, please say that. Yes, this can be scary because they might not feel the same way. And you’ll never know if you don’t say. And it will give you practice confirming what you want to do next and saying it out loud.
“If you didn’t enjoy your time with them then say it’s been nice meeting you and I’m not interested in going out again. I will usually say why I think I’m not a match for them because that is certainly part of the reason for my no-thank you to another meeting. Or something like I’m not as religious as you. I’m not interested in the things that are important to you. I wouldn’t participate in the things you spend a lot of time doing.”
Tom’s comments: Men Are From Mars, Women Are From Venus, the title of John Gray’s book, certainly applies to these responses. Please remember, Bill only made the comments and shared his thoughts with me, not with Jackie. He paid the tab and didn’t mention it to Jackie.
Give Bill a break. He agreed to share his personal thoughts and obviously his comments struck a chord. He later emailed me again saying, “I will wait and see if she contacts me. That could be a big clue. Probably nothing will go forward with Jackie. That’s ok.’
And then he wrote again. “I texted Jackie a thank you and a Happy Mother’s Day. She did not respond.”
This story reveals why online dating is difficult for seniors. If it works, great and if it doesn’t? Oh well, move on!”
The responses to last week’s article made me think of the song by Bill Haley and The Comets (1954) titled, “Thirteen Women (and Only One Man in Town).” Why? Today, 13 women are featured and only one man.
On Life and Love after 50 eNewsletter May 9, 2025 By Columnist Tom Blake
A senior man’s first-date jitters
Bill, a widower in his mid-70s, emailed me for guidance regarding an upcoming first date with a woman he met on Match.com.
I thought it might be interesting, particularly to our women Champs, to know what a man thinks about before and after a first date with a woman.
Bill wrote, “I met an attractive woman on Match.com. She’s 10 years younger. She and I agreed to meet for coffee at a location about halfway between where we live, a two-mile drive for each of us. From her profile picture, she is pretty. I’m a little nervous. Her name is Jackie.
“We talked over the phone and knew at least we had a good conversation before we got together. That is a must for first-date people!”
“Can you give me any advice?”
I replied, “Is this your first date since your wife passed away?”
Bill answered, “No, I’ve had a few dates, but I’m not exactly Joe Stud, you know. But I’d like to impress her.”
I said, “Relax, I can tell you are nervous. But that’s ok, after all, this could become your future mate. Just slow down and calm down.”
“It goes without saying to wear a clean shirt. Smile when you greet her and shake her hand. No hug or kiss when you first approach each other. Men tend to talk too much when they are nervous. Be sure you ask questions about her. Encourage her to talk. Make direct eye contact with her. Smile. Use first-date etiquette; actually, any date etiquette.”
Bill said, “Thanks, that will help me break the ice. I will talk for no more than 40 percent of the time and ask her questions. Her profile says she still works full time. I will let you know how it goes.”
A few days later, after his first date, Bill sent me an update. “It went okay with Jackie. She is pretty. Will we see each other again? Probably. It could happen, but I’m unsure. Frankly, it wasn’t a great connection. She didn’t ask me many questions. I’m 6’ 1; she’s 5’6”—so that works for me. Not too tall and not too short.
“You kind of know if a woman is very interested, somewhat interested or not interested in you. She is somewhat only. But who knows for sure?
“She is divorced and didn’t talk about her ex at all. When I mentioned my wife, this woman sort of felt bad but had no questions about me. When I talked about my interests, the conversation didn’t go very far, but we stayed with her interests and travels.
“It possibly could go somewhere, but I didn’t think she appreciated the breakfast sandwich and beverage because I would have liked a nice thank you for my effort (liked she kind of expected me to pay and I guess that’s ok.)
“She steered away from future plans. I didn’t ask if she wanted to get together again or make any future plans.
“We didn’t get into politics and talked about schools, kids and travel. I probably could have gotten a little more personal and asked what she thought of me. But I don’t want any rejection. We talked for over an hour, so it was going ok, but probably not a strong connection.
“So where does this go? I’m not sure and I’m not clear about my feelings. I could reach out again, but I may leave the ball in her court for her to reach out to me if she is interested enough. So maybe I will ghost her or send her a text in a week to see how she is doing.
“I mentioned a few ideas about walking together on a hike near the beach or something and got no response on any idea she might have to do something. So, no, the date success wasn’t 100%, but more like 35%.
“At the end, I gave her a small hug, but she wasn’t responsive. So, it left me thinking, ‘Do I want to pursue her anymore?’ Maybe there would be too much work involved. She still works and seems busy. Perhaps some of my thoughts may help her. I want some kind of gratification or some kind of future interest to make me think that she and I want a relationship.
“Oh yes, I said at the very end, ‘Do you prefer a text or a call? She said ‘either.’ So, she could be still in it, but not who knows? Maybe it’s me because of my feelings. I don’t need to start chasing or try to create a fun experience. I see myself spending money on dinners and maybe going nowhere.”
Tom’s Comment: So that’s how a nice gentleman feels. If there’s any message in Bill’s story for women, it’s that if you like a guy like Bill on a first date, be a little more assertive, showing affection like a kiss on the cheek and saying, “Let’s get together again.” And ask him more questions. However, what Jackie did may indicate that she doesn’t want to proceed seeing him and didn’t want to hurt his feelings.
On Life and Love after 50 eNewsletter – April 18, 2025
by Columnist Tom Blake
I had a wake-up call on Monday morning while preparing this week’s eNewsletter. My phone was about 15″ from me on my desktop. The loudest warning alert I’d ever heard from that phone jolted me shortly after 10 a.m. One second later, when the house began shaking, I realized a strong (5.2) earthquake was happening.
I hustled to the rear patio to get outside. I looked to my right. My neighbor Jake was outside holding his phone. I looked to my left. My neighbor Aaron was outside holding his phone. We agreed the quake was a doozie. Over 35 years, I’ve felt four earthquakes while inside my home. This was the scariest. Fortunately, there was no damage.
Like the Pony Express, the mail must go through. Despite unusual circumstances, the eNewsletter must be published. Have a safe week, Champs.
And now, this week’s topic:
Kids Interfering With Parents’ Relationships
A month ago, a woman, Champ, 76, living in the Midwest, wrote me about children interfering with her relationship with a man she’s dated for five years. Let’s call her Jolene. It’s not her children who are creating the problem; it’s her boyfriend’s kids and grandkids who are causing it. She wondered if I had ever written about these kids interfering with their parents’ relationships.
Jolene added, “This nonsupport situation by adult children affects other senior couples we know, in addition to us.”
I checked my Findingloveafter50.com website and was surprised to find that I have written on children negatively affecting senior relationships at least once each year in the 31 years I’ve been writing newspaper columns and eNewsletters.
To read previous eNewsletters, including how kids adversely affect their parents’ relationships, simply click on the website link above and search for the categories section. Once there, scroll down to the “Senior Dating With Children Involved” listing.
I never had children, so I’m not an expert on this subject. However, I was in a relationship for 25 years with Greta. She had four children, eight grandchildren, and three great-grandchildren. I knew how important family was to her. She spent a lot of time with them, which was fine with me. I was often included. I was blessed; I had a wonderful relationship with each one of her family members.
However, somewhat related to this topic, after Greta passed away, I was immediately ghosted by the kids and grandkids. I never understood why, but I guessed it was because she included me in her estate.
The details of why and how kids affect their parents’ relationships vary greatly. It seems to me that often, the biggest reason is money. Kids, I’ve been told by Champs, are concerned that they are going to lose their inheritance to their parents’ mates or lovers. That was Jolene’s boyfriend’s kids’ concern.
Jolene added, “Shouldn’t the children be happy that their father has found love? And shouldn’t they leave our relationship to us to navigate? Rather than being thankful that their dad is happy and well cared for, all that matters to them is the money they imagine they might lose. Such a pity.
“The ironic part of this melodrama is that if they were smart, they would be kissing up to me to get part of my estate when I die! I am the one with the money.” I relate to that comment by Jolene.
Jolene continued, “Today, I spoke with an elderly woman who told me her son was not speaking to her because she had taken steps to leave her assets to her grandchildren and not her children, who were already quite well off. I comforted her by reminding her that the money was hers and she could do with it what she pleased. It was her decision not her son’s decision. She thanked me profusely.”
Jolene finished by asking: “How do Champs feel about children negatively affecting relationships? I’d like to hear their experiences.”
Tom’s comment: Hopefully, Champs will let us know. The details of every situation involving children affecting senior relationships are different. It could be money, jealousy, insecurity, favoring one child vs. the others, missing the deceased parent, or the child’s demand on the parent’s time — whatever on the children’s part, or even on the adults’ part.
If children are affecting your senior relationship negatively (it’s more common than you think), talk about it with your mate to reach a middle ground, and visit a therapist or marriage counselor if necessary.
On Life and Love after 50 eNewsletter April 11, 2025 By Columnist Tom Blake
Included today are comments that 8 Champs shared. The above photo was taken by me in Scotland from the deck of a Holland America Line cruise ship of 8 bagpipers, not Champs, performing on the adjacent pier. Like you, Champs, their performance was glorious.
Joe, recently divorced, emailed, “My dating has been limited to meeting women on dating apps. I had an interesting thing happen at a grocery store. I noticed a cute woman in the store. I got to the laundry aisle, and there she was again, looking at items to buy. Although she didn’t look at me, I was tempted to ask if she was single. I missed my chance.
“My fear was her saying she wasn’t interested in dating me–a comment no guy likes to hear. I am not used to approaching a woman and, after talking to her, asking if she is single. I guess that I might as well try. What do I have to lose?
Tom’s comment: You have nothing to lose, and you might gain a new potential partner. Fear of being rejected applies to both men and women. Remember the woman Champ, who saw a cute guy in the medical waiting room and blew it by not talking to him?
Single men and women should carry a business card or a card that lists their first name and a safe phone number or email address they could hand to a new acquaintance. In that way, the person could reach out to you if they find you appealing. Like on dating sites, you might experience rejection, but that doesn’t mean you shouldn’t try.
Terry, “I met with my ex-wife this morning to sign all the divorce papers again. My California attorney made mistakes in the original filing.
“My ex was very angry, even though she was the one who left me. The good part is that I think her anger helped me realize that our divorce was the best thing. “With the trouble I am having securing this divorce, I will never legally marry again. This was my fourth and last marriage.”
Alison, 68, “I have enjoyed reading your articles for many years. Widowed three years ago, I ventured into the senior dating scene at the urging of good friends. They introduced me to a widower friend of theirs. We dated casually for a year before deciding to get involved more deeply. We are great companions, have similar interests, and enjoy each other’s company in many ways. He is 78.”
Cynthia, “I lost my husband many years ago and have not met anyone whom I feel chemistry like I felt before. Not to say the men I’ve met aren’t nice, they are, but it just hasn’t happened.
“However, the good news is I moved forward emotionally and physically. I’m now living in RMV (Rancho Mission Viejo, Ca.), a wonderful & great active 55+ community. And I’ve developed many new friends to boot! “I’m content with my life for now. I feel happy and grateful for who, what and where I am. And I am blessed to have reached peace of mind within myself.
“Your articles help seniors feel good (or at least better) about themselves and their situations.”
Kaitte, “I can’t believe it’s been three years since your partner passed and you’re happy again. I haven’t given up dating, it’s just that I haven’t met anyone who doesn’t make me feel like they’ll put me in a cage with their boundaries and first-date sex. And that’s before I even find out if I would like to get to know them. This cow is not for sale.
“I’ve built a good life on my tiny 1.5-acre Colorado farm over the last 10 years. I planted 1000 Spring bulbs that were at a clearance sale at Walmart in November– $500 worth of bulbs for $100. I bought them all, and they are everywhere. A man would have to be very open-minded and have his own life like yours. Give me my space.
“I don’t want a relationship that disrupts my life but adds to it.
Relationship coach Christine Baumgartner and you mention that I must give a guy a chance. I agree, but you usually know after a couple of dates if it’s going to work.”
Carolyn, “Tom’s recent romantic connection gives me hope for the future. I’m still out here looking and still enjoying myself with other like-minded seniors. “I am 73 and active. Unfortunately, many men I encounter have health issues and many walk with a cane. Not a problem for me but they aren’t able to walk too far and fall asleep a lot!
“I always enjoy conversing with all the people I meet at the senior socials. To combat loneliness, seniors should consider joining senior centers. Those places provide many activities and social events. I absolutely love my senior center!”
Ray Freer, Laguna Woods, Calif.“ Last October, you wrote about my marriage to Libby here in Laguna Woods. We are in our mid-80s. The current buzz around the Village is an event, scheduled for Sunday, May 4 at the Outlets at San Clemente, ‘The Rotary Route: South County Walk for Mental Wellness.’ (10 a.m. to 2 p.m.)
It’s sponsored by nine Rotary Clubs across South Orange County! “Several of our Laguna Woods friends are participating. I mention the walk, thinking that nearby Champs who seek social interaction, making new friends, physical exercise, and support of a worthy cause might want to participate.
Tom’s comment to Ray: Thanks for the tip. Debbie and I will be joining you and Libby on the May 4 walk. Married life appears fun and rewarding for you two lovebirds.
Michelle, “I live in Dana Point, California. I know a few Champs who reside in Orange County. What wonderful people. I asked Tom if he would mention that I am seeking a woman roommate to share my casita. It’s a half mile to the beach. Life is better when you aren’t living alone. Email me at michellvrv@gmail.com. Here is the property listing on furnished finder: https://www.furnishedfinder.com/property/594302_1
Tom’s comment. Michelle lives in a beautiful casita and is a wonderful person.
On Life and Love after 50 eNewsletter – February 21, 25
By Tom Blake, Columnist
On Life and Love after 50 eNewsletter – February 21, 2025 By Columnist Tom Blake
You Talk Too Much (About Yourself)
Champ Susan emailed this week: “I’ve been reading your weekly column for years. Seeing you go through the horror of losing your soul mate and you following your advice to find a new mate.
“I’m 63, living in Dana Point, California, and have been single for 12 years. A couple of short-term relationships in between. I’m perfectly happy living by myself—thin, attractive, and smart. Reading about health, the experts say that a meaningful relationship adds to your health. So, I joined Zoosk, Match, and Facebook dating.
“In three months, I’ve had 4 dates with different men. On each date, the men only talked about themselves. What is up with that? Don’t they understand the difference between a conversation and a lecture? It’s not a job interview. Either you like each other, or you don’t. Why don’t they want to know more about me? I want to know about them.
“I had a 5th date yesterday. I had to laugh at him. I have an S-class Mercedes, and he has a Tesla. He looked at my car and said, ‘OMG, you have two exhaust pipes.’ He was serious. I don’t think he will date me again.
“I’m frustrated with online dating. I don’t like Zoosk because they send you this carousel of men, but you can’t see where they are from or anything about them until you like them. Not having any luck on Match as far as getting dates. Everyone that likes me is 60+ miles away. I specify the distance, but it only makes a difference when I search, it doesn’t stop others from writing to me from far away.
“Facebook dating is free, and I get the most local people to evaluate. Am I missing something?”
Tom’s comment: “Why do the men you’ve dated only talk about themselves? I imagine they are nervous, perhaps fearing that you won’t like them, so they must tell you all the positive things about themselves. They don’t understand it’s common etiquette on a date for each person to share the conversation, especially on the first date when impressions are so important.
“Perhaps, they are intimidated by you and feel you are out of their league. They may be talking nonstop about themselves to convince you they are worthy of your attention.
“So, Susan, keep trying to meet men. Perhaps change the online dating service you use. In addition to online dating, get out and about in your city of Dana Point. Meet new people. Senior dating is a numbers game.”
That each of Susan’s four dates talked too much about themselves and didn’t ask about her is puzzling to me. I don’t have a good answer. I think it’s time for Susan to get an opinion from a therapist. It might be that she is doing something wrong by attracting strange men.
I remember the novelty smash hit song, “You Talk Too Much” by Joe Jones. When it was popular in 1960, I was in college at DePauw University, Greencastle, Indiana, and scored a date with one of the most attractive women on the campus.
She dominated the conversation about herself, and that song kept popping into my head while she chatted away. I didn’t understand why she was talking so much about herself. I guess she didn’t want a second date with me so she figured if she dominated the conversation, I would realize the date would be our only one. She was right, we didn’t go out again. But we remained cordial friends.
When Susan emailed me her question this week, it reminded me of that date 65 years ago. What a riot! Both senior men and women should remember conversation etiquette on first dates and all dates. If conversation slows to a standstill, or your date is talking too much about themselves, ask him or her a question like, “Would you like to hear a bit about me?” That question would be a good reminder for them that they are talking too much.
My buddy Jim says it’s also important to make eye contact with your dates, and they should make eye contact with you. If the one-way conversation continues, consider rolling your eyebrows, yawning, or rubbing your nose. If the question and the gestures go right over their head, that person isn’t the right potential mate for you. He might be a narcissist, unable to adapt. A final somewhat unrelated thought. What did Susan’s Tesla-owner date mean when he commented about her two exhaust pipes? That guy sounds pretty strange to me.
So, Champs, let’s hear your opinions about Susan’s issue. And one new item. Since Champs have been asking me about therapists lately, I’ve decided to implement a new eNewsletter feature. It will start in next week’s newsletter and appear every other week, at least for now. It will be called Ask The Therapist.
The way it will work: Champs will email me with Ask The Therapist words in the subject line. Then they will write out their question within the body of the email. Limit 50 words. I will share the question with Champ Debbie, a therapist, and my significant other, and she will write her reply in an upcoming eNewsletter. We will give it a try and see how it goes. Only first names will be used. Your city is optional. This feature will appear at the end of the eNewsletter.
On Life and Love after 50 