2 Senior Women With Different Retirement Outlooks

On Life and Love After 50 eNewsletter

By Columnist Tom Blake

NL May 23, 2025

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.

False Hope


On Life and Love after 50 eNewsletter – January 10, 2025

By Columnist Tom Blake 

False Hope – A Champ’s Dilemma 

The names of the people in this eNewsletter have been changed by request.

Last week, Champ Ann emailed me, saying, “I need advice. A woman friend named Judy, who lives nearby, recently mentioned to me that she had a conversation months ago with Ben, a neighbor whose wife has had Alzheimer’s for 10 years. The wife requires 24/7 care.

Ben told Judy that he takes care of his wife with the help of several other caregivers.  “Judy raves about Ben’s dedication to his wife. He refuses to put her in a care home She is expected to pass in 2025. Ben admitted to Judy that he was lonely.

“This was months ago. I told Judy to give Ben my phone number, as I am lonely as well and maybe he and I could meet occasionally for coffee. I didn’t hear anything until Christmas Day 2024 when I got a call from Ben.

“We had a nice conversation and agreed to meet the Saturday after Christmas at my house for coffee. I understood–it would be too awkward to meet at his home. I made sure my friends knew I was having company. I already knew he was very kind, loved his wife and did not want to put her in a home, although it would have been easier to do so. It’s quite a challenge for him to care for her even though he has lots of help.

“On Saturday, Ben came to my home. We talked for hours. I liked him right away. That is how we got together, neither of us expected an attraction. When he left, he kissed me twice.

“On Sunday, I attended a party with my grief support group and didn’t check my phone until later. Ben had left a message, saying he wanted to pick me up and have a bite to eat. I had eaten already so I invited him to come over for a glass of wine, which he did. I was happy to see him. He brought a bottle of wine and again, we talked, but mostly with him talking. I sensed that he needed to do that.

“Suddenly, he pulled me close and kissed me a few times and said, ‘You are my girlfriend,’ and almost immediately he released me and said, ‘No, we need to take it slow.’ I think he scared himself and withdrew. I also said we needed to take it slow, and we needed to be honest about it. He left not too long after that; I didn’t think too much about it. We agreed to try to see each other Monday, the following night.

“He told me that one of the caregivers may not make it and that meant he would have to do the shift for caring. However, if the caregiver did come, then he’d be available, and he and I would do something together.

“Monday, I didn’t hear anything, so, in the evening I sent a text saying hi and were the plans for tonight still on.

“I got a text back saying that he had to care for his wife and had the 6 pm to 2 am shift. ‘Sorry’ is how he ended that text. Five minutes later he sent a text saying, ‘I apologize for sounding so cold.’

“His reaction took me aback. Minutes later I sent a text saying that I understood his responsibility and that I was having a glass of wine.

“Ben answered, ‘You are a special lady’ and he was having a beer.  

“On New Year’s Eve, he texted me to come over as he was in his hot tub and made it a point of saying in his birthday suit. That didn’t bother him.

“I declined politely. It would feel wrong to be in his house when his wife was in another part of the house, and me making out with her husband. I haven’t heard anything from him since then.

“So now, Tom, I am stuck, what happens next?” I will not text anymore. His ‘special lady’ comment feels like there is a ‘but’ coming after it. Something like, ‘I cannot have this friendship with you’ or ‘I thought I was ready.’

“Fill in the blanks, I don’t know what to think and maybe I am making too much out of this. Maybe he drew back to give himself time, or maybe he scared himself with his intimate outburst.

“Partners who take care of terminally ill partners who have been sick for a long time must want to get out and socialize, but they might feel guilty doing so.
“Ben is attractive to me, not so much his looks but his kindness. I want that and I want him but now my fear of rejection and loss has set in.

“I am so sad and feel so alone with tears on this last day of the year.” 

Ann’s Update 

On the day after New Year’s Day, Ben sent a text to Ann that he had written on the day after their second date at her home.

He wrote, “Hi Ann, thank you for the special time we had together last night. You’re a precious, compassionate and very kind person, however I spent a lot of time last night thinking about our relationship and where it’s heading. I realized I’m just not ready at this time as I have so many responsibilities that require my full attention, mainly my wife. You and I agreed to be honest with each other.  

“I sincerely apologize as I know this will hurt you and it’s the last thing I want for you. Maybe later in the future as my situation changes, we can continue our companionship but only God knows that. 

“Your close friend, Ben” 

Ann said, “I didn’t mean to fall in love, I just did and followed the cues from Ben. Remember, I didn’t go to his house to join him in the hot tub. That felt wrong. Ben is so lonely. Many of us deal with that and I still deal with that.”

Tom’s Thoughts 

Ann is devastated. She fears he won’t contact her again. She sent me several emails saying how sad she was and should she respond to him. Two similar situations happened to her in the past, which is likely why she is taking this rejection so hard. 

 I told her I am not a therapist, so I don’t have the answers, but that she probably shouldn’t contact him. Let him stew on it.  

But then, after receiving several sad emails from her, I suggested that maybe she should contact him to tell him that she respects him, but the ball is in his court.  And I suggested to Ann that she should consider contacting a therapist about why she is so devastated.  

What do you Champs think?

A Senior Love Story

On Life and Love after 50 e-Newsletter – October 11, 2024
A Senior Love Story
By Columnist Tom Blake 
In August 2021, Ray Freer, 80, a widower, moved from Park City, Utah, where he had lived for 30 years, to Laguna Woods Village, a 55-plus private community of approximately 18,000 residents in Orange County, California.

He moved to Laguna Woods because he loves to play tennis. I was introduced to Ray by my friend and fraternity brother, Tom Brunkow. Tom and I met 67 years ago in 1957, as freshmen in the Beta Theta Pi fraternity at DePauw University, in Greencastle, Indiana.

Tom Brunkow is in the DePauw Athletic Hall of Fame for his tennis accomplishments. Ray has won multiple tennis tournaments and through tennis is how they met. 

Ray signed up for my eNewsletter on December 21, 2021. Emails Ray sent me over three years are included below. 

Ray’s December 21, 2021, email Ray wrote, “Went to a dance. I found it very awkward. On either side of me were a married woman and that sort of protected me. They were not on the market. Across the table were six unattached women. That intimidated me.   

“I play racket sports (Tennis, Paddle and Pickleball). There are lots of attractive women doing that, which makes it easier for me to talk to them one-on-one.  “In Laguna Woods almost everyone is friendly. I haven’t connected with a woman yet. I am sure my time will come. If lightning strikes, I will pursue it wholeheartedly. “Octogenarian (80) Ray of Hope.”

Ray’s April 11, 2022, email Ray emailed “Life here in Laguna Woods is good and getting better. There are quite a few LATs (living apart together couples) here.  

“It’s lonely. I haven’t found anyone, but all is OK. The good thing about the activities is they allow a person to meet others with similar interests before getting deeply involved. The activities provide time and opportunities to meet without commitment. 

“The demographics here in Laguna Woods suggest seven or eight women for each man. Here’s how I estimated the ratio (the numbers are approximations): The population of Laguna Woods is 18,000. Six thousand are men and 12,000 are women. Assuming 5,000 of those men are married, that takes away 5,000 from the 12,000 women. So, 7,000 available women are left with 1,000 available men. 

“Many people have significant others here. Some women, consistent with a lack of interest, just are not available. But that still suggests there are lots of ladies out there.   

“It is weird being out there at 81. Many of the women with whom I talk say that the only thing men want is to get into the sack with them but with no real ongoing relationship. Some say it’s not worth the bother. Many simply avoid the dating scene entirely.” 

Ray’s October 14, 2022, email “It is just my impression, but when a couple starts sleeping together the relationship becomes more emotional. At some level that implies more of a commitment. “I enjoy senior sex, but I have not been pursuing it because I don’t want to hurt the other person by not following through with an emotional and enduring commitment.  

“The other side of that is I am picky so that is frustrating as well. I suspect I am not unique but, ‘Who knows?’ 

“I have some lady friends that appeal at one level or another, but it just hasn’t reached the ‘Let’s get physical’ stage a la the Olivia Newton-John record. I suspect it will come but who knows when? It’s a conundrum. 

“The final issue is, while someone might appeal to me, it does not necessarily follow that I would appeal to her. It wouldn’t be her fault if I didn’t float her boat. 

Ray’s February 10, 2023, email “I read your list of 12 characteristics in your eNewsletter. I never made a list of characteristics wanted in a mate, but it makes sense. Also, in concert with your eNewsletter, I have never sought a replacement for my wife Mary. On the other hand, I do seek a person with some similar traits she had.”  

“Regarding your question about my involvement with a person here. I am involved with a gal named Libby. Her father taught me how to play tennis She checks off a lot of the boxes on the list. I keep thinking it might come to pass, but so far, no real heat. She has lived in Laguna Woods for more than 10 years. 

May 2024 In May 2024, My woman friend Debbie and I were invited to dinner at Ray’s home with the Brunkows in attendance. Ray and Libby had become a committed couple. 
Senior marriage at 83

Ray’s September 27, 2024 email “Libby and I married on June 29, 2024. We had lived together for a year and a half. She sold her condo and moved in with me. We have known each other for 74 years. When we were kids, she was a year and a half older than me. When I was in 5th grade she was in 7th, an unbridgeable age gap at the time.  

“Now at the advanced ages of me (83) and Libby (84), the age gap isn’t an issue. I refer to her as a cougar robbing the cradle.  

“I play tennis frequently. Libby walks daily and I join her three days a week. Both of us go to the gym regularly. We are healthy and that is why we married. We simply want to live those twilight years as positively as possible. 

“Your list of twelve questions to discuss to determine compatibility was very helpful. We are so boring. We were similar in answering every question. We appreciate each other and are fortunate to enjoy many of the same things. Your eNewsletter helps many seniors.” 

Tom’s comment: Wow, Ray and Libby’s story shows why single seniors should never give up hope. The coincidence of marrying someone he knew for 73 years is mind-boggling. And exciting.
Ray and Libby Freer wedding June 29, 2024

photo courtesy of Ray and Libby Freer