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.

Older women dating older men

On Life and Love After 50 eNewsletter – Older women dating younger men is a hot-potato topic

by columnist  Tom Blake

Champ Jackie “from Georgia” has paid her relationship dues. She was divorced after 42 years of marriage. Five years later, she attended her 50th high school reunion in Michigan.

At the reunion, she met her classmate Randy and married him a year later. Just two months after they married, Randy was diagnosed with cancer. For the next five months, until he passed, Jackie was Randy’s caregiver. I met this very delightful woman and her sister at a Dana Point, California, Meet and Greet in May, 2019.

Responding to last week’s eNewsletter, she wrote: “My question: ‘Does age matter when it comes to women being older than men? After my dedication to Randy, I don’t think I could willingly do it again. At my ‘young age’ of 72, I’d want someone younger”

I will tackle Jackie’s question, with this disclaimer: It’s a hot-potato topic because there are so many different points of view on older women dating younger men.

In the past, when I have written on this older dating younger subject, I’ve been dragged over the coals by young women, older men, older women, bitter men, bitter women, religious zealots, breadcrumbed victims, and people who enjoy, even relish, controversy.

Inevitably, no discussion about older women dating younger men would be complete without mentioning the dating term “cougar,” a label or term of which the origin is unclear. It’s thought possibly to have come from a Canadian dating website.

I don’t particularly like the term, but then, I don’t like a lot of the terms that have labeled senior dating. Heck, we seniors are just trying to muddle through and enjoy life the best we can; why do we need so many labels to describe us? I guess the term “cougar” is okay, but I find it to be a bit demeaning.

If older women want to date younger men, what the heck is wrong with that? Let’s just label them normal instead.

The epitome of cougarhood (another new term) was Mrs. Robinson, in the Dustin Hoffman movie, “The Graduate.” Of course, she was a married woman, which made the relationship uncool.

Okay, with “cougar” out of the way, let’s continue.

Jackie is not the only widow who feels she doesn’t want to experience widowhood again.

About three years ago, I fixed up (remember, I’m not a matchmaker) a widow, age 60, with a friend who I guessed was about 70. They were both ocean-orientated buffs, so I thought it was a good similar-interests match. She an outrigger paddler, he a boat skipper.

I saw them enjoying a beverage together shortly thereafter at a gin mill. At that time, I thought to myself, “bingo,” a good introduction.

Nope, she told me a couple of days later that she found out he was 75–not 70–and she didn’t want to take the chance of becoming a widow again. So, it’s not just Jackie who is avoiding dating men her age and older, hoping to avoid being “Widowed” again.

Even if older women do date younger men, that doesn’t mean they won’t be widowed. In all relationships that go the distance in life, one of the partners is likely to die first, unless something happens when they are both together and they pass simultaneously.

I accessed the archives of articles I’ve written about older women dating younger men on my Finding Love After 50.com website. Here are a few of the important points from past eNewsletters:

I wrote, “A surprising trend surfaced. Several women said they are attracting considerably younger men.”

Ann responded to that, “I’m 72, and for some unknown reason, I attract younger men. I’m asked out on dates and have received two flower arrangements from younger men in the past two weeks. I try not to be involved at my age because of the great chance of making a mess of my life.”

Ann also said the reason she doesn’t date men older than she: “If I were to date my age, 72-82, I’d be taking my life into my own hands every time they drive. Some of them can’t drive at night but they have two-three drinks. Sorry, I like my life but don’t want to end up dead or in a wheelchair.”

In another older women dating younger men article, Brenda said, “I recently dated a guy eight-years-younger. He treated me better than any man ever has. I’m not sure what happened but it ended suddenly after just six months of seeing each other.

Note from Tom: This is one of the things that can happen when older people date younger people. The younger one fades away. Maybe even does ghosting. So, that’s another consequence that one should be aware of before dating someone younger.

What is a significant age difference?

A key question: what is a significant age difference? Five years, 10, 15, 20, 25+, who’s to say? If a woman is dating a man 25-years younger, chances are, he’s going to become a widower, so he needs to accept that possibility.

If there is a significant age difference, each partner would be wise to understand his or her own motivations for being in the relationship, and the partner’s motivations.

Understanding those motivations, what the heck is wrong with being in a significant age-difference relationship?

Be aware, there will be challenges. If there are children on either side, that may muddy the water. And there could be negative stigmas from the general public. Imagine someone saying, when she sees you in a restaurant, “Hi Ellen, I didn’t know you had a grandson.”

Bottom line: Everybody’s different. There’s no right or wrong. Enjoy your life while you can. It’s nobody else’s business except the two people involved. So, go for it, Jackie.

Link to Simon and Garfunkel’s “Mrs. Robinson.

https://www.youtube.com/watch?v=9C1BCAgu2I8