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.
A good place to meet men. The Palm Springs, California Air Museum. One of nearly 100 vintage airplanes on display
On Life and Love after 50 eNewsletter May 2, 2025 By Columnist Tom Blake
Is 83 too Old to Date?
In the March 21 eNewsletter, Champ Susie commented, “Question: how does a woman become attracted to an older man? Or, if you are a man, how do you become attracted to an older woman? I am 83 and take good care of myself. I still look pretty good after years of working out and being a dancer. I never let myself go.
“I want to go on a dating site, but my age of 83 stops me. I would not be interested in a man 83, and I figure no one would be interested in me at 83.”
This week, Champ Leslie responded to Susie’s above comment.
“This is addressed to Susie at age 83. You never know where or when you might meet someone. Though my man friend and I met at 75, we are each 83 now. The last two men I’ve been in long-term relationships with, each for eight years (the previous one was from 2001-2009), were both from my high school class. I chaired the reunions when we connected both times. The current 83-year-old is still active.
“I live near the Villages in Florida, and people here meet constantly. My significant other lives 90 miles north of my place, close to Tampa, and we’re usually at his place. Being your age, Susie, I understand how you feel about online dating.
“I know of a man who had never married, and he married someone also from my high school class. None of these relationships were from online dating. Both members of this last couple were volunteers for Meals on Wheels.
“Tom, I look forward to your eNewsletters; they’ve helped me very much these last several years. Thank you for sharing last week’s article about the dolphin rescue. Dolphins are amazing animals. I am also on the Quora website you mentioned last week.
Tom’s comment:
Seniors who are willing and able to get off the couch, out of the house, and involved in activities increase their chances of meeting a potential mate. Leslie makes a good point. She met her last two partners when she chaired her high school reunions. Even if you don’t serve as the reunion chairperson, still attend them if you are seeking a mate near your age, with the added benefit of sharing the common bond of having attended school together.
Eight years ago, I wrote a column about two of my high school classmates who never dated each other, but he managed to track her down 50 years later. She lived 2,000 miles away. He told me, “I always had a crust on her.” To say the least, I was shocked when they got married and appeared at my doorstep “just to say hello.”
Not only is volunteering a wonderful way to help people, but it also exposes you to people you would have never met. Leslie mentioned Meals On Wheels as an example
Other activities include playing pickleball or other sports. Attending church and Chamber of Commerce events and walking your dog is another thing to do.
This previous weekend, my significant other Debbie and I were in Palm Springs. On Friday, we visited the Air Museum, located across the main runway from Palm Springs International Airport. It’s known as the best Air Museum in the USA. I highly recommend adding a visit there to your Palm Springs “must-see” check-off list. There are nearly 100 vintage warplanes dating back to WWII, including the photo above.
You can also sit outside and watch the commercial jets arriving and departing at Palm Springs Airport with the best seats in the desert for doing that.
But here’s my point about the Air Museum. It’s a place to meet people. It’s manned totally by volunteers, women and men. Those volunteers interact daily with multiple museum visitors. Most of the volunteers are seniors and men. What a wonderful place to volunteer and visit (and maybe meet your potential mate).
Leslie makes a good point about online dating in our 70s and 80s. It’s a challenge, but it can still work. Posting a photo of oneself when we are in our 80s is frightening (voice of experience). I understand Susie’s hesitancy to do so. But it can work, I met Debbie online (on Zoosk) two years ago when I was also 83.
However, getting off the couch and meeting people face-to-face is a better way for seniors to meet potential partners compared to searching online.
Scam Alert
This Monday, while I was preparing today’s eNewsletter, unexpectedly, my computer screen locked, saying Microsoft Security was protecting it and I should call 855-793-6220. I sensed a scam and shut off my computer 3 times, and the screen was still locked when I turned the computer back on. Then, I remembered the magic of CTL-ALT-DELETE, holding down all 3 keys at once. That did it. The screen was unlocked when I tried to open it the next time.
I checked online with my backup computer, and a search revealed that the phone number is a scam.
On Life and Love after 50 