On Life and Love after 50 eNewsletter – On Life and Love after 50

Two Tuesdays in July 2025

On Life and Love after 50 eNewsletter

by Tom Blake Columnist

Last week’s eNewsletter was titled The Sound of Silence. It was based on a Paul Simon concert that my significant other Debbie and I attended in Long Beach, California on Tuesday, July 8.

Here are a few responses from Champs to that eNewsletter.

Kathy, “OM Gosh great newsletter! Saw Paul Simon and Art Garfunkel twice – last time was some months after 9/11/01 at Madison Square Garden and the other time was way back in the 60’s before they became who they became. I’ve been an ardent admirer of Simon forever and think of him as a genius.

I’ve seen the movie The Graduate several hundreds of times Scarborough Fair is one of my favorite songs as is April Come She Will but there is a Simon and Garfunkel song that I think is hauntingly beautiful and ranks as one of this gal’s favorites; For Emily whenever I might find her.

I love that Paul also wrote a song with my name in it, Kathy’s Song. Good memories, great music.

Carmen, My high school classmate, “My favorite line from the song is “The words of the prophets were written on the subway walls and tenement halls …

“I also liked Kodachrome.

“I dated a woman when I worked in Mexico City who dated Paul once.”

SW, a woman co-worker at the Victoria Station restaurant chain. “Beautiful column, Tom!!

“I went through a phase of listening to one of the Simon and Garfunkel CDs in my car this year – absolutely love them – and The Graduate!

Margo, “In college, I took a film class. I made a movie using the music and lyrics to “The Sound of Silence.” I think it was pretty good. I’m disappointed I never went back and retrieved the films I created. It remains one of my favorites.”

Gloria, “Another newsletter near and dear to my heart. The Sound of Silence.

“I have always loved the song and most of the other songs you mentioned; The Boxer, Slip Sliding Away and Homeward Bound.

“I saw The Graduate a few times. One of my other favorite songs is Mrs. Robinson. When my grandchildren were smaller, I would take them out for pizza and played that song in the car as we all sang along. To this day, if any of them hear it, they text or call me and tell me all about it.

“Such insight from Simon to have written those words so long ago.”

Francine “Simon and Garfunkel both grew up in Forest Hills, Queens (NYC) where I lived from 1965-1968. Forest Hills is home to the Tennis Stadium which used to have a lot of concerts. I lived right down the street and heard the concerts for free, including Simon and Garfunkel. The Graduate was an amazing movie.

Ted, a high school classmate, married 60 + years: “The Sound of Silence is my favorite Simon & Garfunkel song. Closing the show with it was perfect! Yes, Debbie won the one-dollar bet. Where have the year’s gone?”

Beckie “I’m probably not the 1st one to tell you the song was on a 33rpm record, not a 78rpm as you mentioned. “The Graduate. Fine movie, wonderful songs.”

Julie, “All your columns are wonderful, but this one is my new favorite. You have a way of tying things together and putting the reader right inside these events! Who doesn’t love The Graduate and Simon and Garfunkel?

“This is how I live my life too! Acting on opportunities that seem to drop in my lap. I guess you and I both connect with people. Our open minds and hearts keep the fun coming from many unexpected places (e.g., The Racker neighbors)

“May you continue to experience these fruits of your relationship-building, and a life well lived! Including the physical stamina to climb into a concert venue. I’m cheering for you!”

Carolyn, “Wow! Loved reading this beautiful eNewsletter! Jake and Kresta Racker are amazing friends to have!

“As of this April, Simon and Garfunkel were speaking again and talking about a possible concert featuring both. I always keep hope alive for this make-up, break-up duo. I love them and value their delicious music. Always so heartfelt and true.

“Super happy that Simon came out at the end to sing that beautiful Sound Of Silence. (Debbie won the $1 bet fair and square!) Fingers crossed that I shall see them sing together one last time. The Graduate has always been a fan favorite”! Phenomenal acting!”

Tom’s speech on Tuesday, July 15

Approximately 50 people attended my speech at the Susi Q Senior Center in Laguna Beach. I was pleased that the events coordinator Christine Brewer had all the equipment working perfectly. My buddy Jim Fallon advanced the Power Point slides with a remote gadget when I gave him the nod. Overall, I thought it went well.

Champ Wayne mentioned to me that the ratio of single women to single men attending to be about 5 to one.

For me, the heroes among the attendees were Ray and Libby Freer, a couple in their mid-80s who married in June 2024. In the slides, I had included as the final slide a photo of them walking down the aisle after their marriage as a sign of hope that romance can happen after age 80. There had been a gap of 70 years since they had seen each other. I didn’t know they were coming to the speech. Both shared their story and advice with the audience during the Q & A at the end.

In particular, Ray stressed that a characterists-wanted in a mate list I had included in the February 10, 2023, eNewsletter helped him and Libby decide they were well suited for each other to marry. I checked the archives and found that list and am including it here.

Tom’s Suggested List Of Characters Wanted in a Mate

1 He makes me his top priority and treats me with respect

2. I am physically attracted to him. And he to me

3. We must enjoy being together and feel comfortable

4. He must not smoke or take drugs

5. He must be financially self-sufficient and willing to share expenses

6. He takes care of his health

7. He must be available to see me three to four times per week

8. We don’t have to have similar interests, but similar core values

9. He must be kind and considerate to others

10. We must agree on politics

11. Our religious beliefs don’t have to be the same, but neither of us can be zealots or closed-minded to the partner’s beliefs

12. He must be open to having a new relationship. We must be able to talk about our former spouses and mates without the other person feeling jealous or compared to. If a person talks about a former mate incessantly, that person is likely not for you.

End list

Yes, it was a busy two Tuesdays in July.

Finding Love at 30,000 feet

On Life and Love after 50 eNewsletter

Tom Blake Columnist

The May 9 eNewsletter was titled, “A senior man’s first-date jitters.” The man was Bill, and he described his date with Jackie. Bill felt Jackie didn’t have an interest in him. They didn’t go out again. In that article, I shared my opinion about Bill’s date.

There were many responses expressed by Champs, offering advice for both Bill and Jackie on how each could have improved their hour-long date.

Two weeks later, Champ Mike emailed me about that May 9 eNewsletter.

Mike wrote, “You, Tom, do appear to be a very nice, compassionate guy in your response to Bill. Frankly, I thought there were enough clues early in the date for Bill to cut the date short and say, ‘It’s been nice meeting you’ and leave.

“I was divorced and single from age 45-60. I dated first with referrals from friends, then dating services like “It’s Just Lunch,” and finally tried some online dating sites.

“I found my love at 60 and have now been married 20 years.”

I responded to Mike: “How did you meet your wife? Online? Or otherwise?

Mike wrote, “I met my wife on a Delta flight. She was a Delta Flight Attendant. It was on one of the first flights leaving Cincinnati after 9/11. The airplane, a 757, was virtually empty, very spooky.

“Everyone was nervous to fly, including the employees

I was traveling with, and my son, to visit my brother in Hartford.

I was seated in first class, no other passengers were up there, and Kathie was the Flight Attendant. We talked for the entire 2-hour flight. I thought she had to be married, but my son said he didn’t see a wedding ring.

“A few months later, I ran into Kathie at the airport as I was leaving for a flight, she was leaving at the gate next to mine. I immediately asked for a dinner date. She accepted, but due to our travel schedules, it was a couple of months before we could. When the day arrived, she preferred to pick me up, since she had two kids, age 2 and 4, at home.

“When she arrived, standing in the doorway framed by the overhead light, she took my breath away. Unrecognizable from her plain flight attendant uniform, she was stunningly beautiful. I never dated anyone else again. We dated for two years, were engaged for one year, and this June 4th was our 20th anniversary. As close to love at first sight as it gets.”

As often happens with Champ’s stories, Mike’s story struck a chord with me. In 1963, after serving in the Navy during the Vietnam War, I was discharged from the Naval Auxiliary Air Station in Fallon, Nevada. I boarded a military flight in Fallon to the Bay Area, where I was to catch an American Airlines flight to Detroit, near where my parents and sisters lived in Jackson, Michigan.

The military flight was delayed, so I missed my AAL flight home. I rebooked an overnight flight from SFO to Detroit for that night. Like Mike’s story, I spent at least two hours on that flight talking with the stewardess (that’s what they were called then).

Her name was Linda. She was based in Chicago, and we dated for several months while I was at the University of Michigan Business School getting my MBA. To see each other, she would schedule flights with layovers in Detroit. I would pick her up in my rattle-trap ’57 Chevy at Detroit’s Metro Airport.

After graduation, I worked for AAL so we met often. She was, like Mike’s wife Kathie, a cutie. I clipped out a Fortune Magazine American Airlines advertisement in June 1965, because it reminded me of Linda.

Sixty-five years later, I have the original of that advertisement buried somewhere in my garage archives. I found a copy online, which is the photo above, entitled “People keep stealing our stewardesses.” I was one of those guys, sort of.

The small print in that ad reads, “Within two years, most of our stewardesses will leave us for other men. This isn’t surprising. A girl who can smile for 5 ½ hours is hard to find. Not to mention a wife who can remember what 124 people want for dinner…”

However, the relationship with Linda fizzled out due to long distance.

But, my infatuation with flight attendants didn’t end then; I married a Pan Am flight attendant four years later in NYC.

If there is a lesson to be learned from today’s eNewsletter –- and it’s a stretch, I admit — if you’re single and when you travel, strike up a conversation with flight attendants (now both women and men), train conductors, pilots, and other fellow travelers, you just might meet the love of your life. Mike’s story and my story are proof that love can happen at 30,000 feet.

Share with us how you met the love of your life while traveling.

Deceased partner’s photos

By Tom Blake, Columnist

On Life and Love after 50 eNewsletter June 6, 2025

Senior Dilemma. When should a deceased partner’s photos and belongings be put away?

A woman recently emailed with a heart-wrenching question that many seniors face. She requested to remain anonymous, so I shall call her Sue.

Sue wrote, “I met my sweetheart online a year ago. Although he lives 30 miles from me, he says it’s worth the 40-minute drive. I am happy he feels that way.

“What are your thoughts on my him still having his dead wife’s clothing in their closet? She passed away 10 years ago. I discovered this when he invited me to spend the night at his place, when I took my overnight bag upstairs. Additionally, all her old perfume bottles are displayed on the master bathroom counter. It was disconcerting to me to say the least.”

“I appreciate your feedback. Thank you.”

My reply to Sue

“I understand the dilemma. Greta, my partner of 25 years, passed away 2 and ½ years ago. I have many pictures of her and us together around my home. I am slowly moving the pictures to a box in the garage. I realize my life has changed and it’s time to move on.

“It’s hard as the pictures represent so many memories, but I need to do it. Thanks for the reminder. Let me know how it goes.

Your question gave me a nudge.

“In your situation, Sue, especially with your boyfriend being a widower of 10 years, the woman’s clothes in the closet need to go.

“Plus, no woman is going to want to use the left-over perfume bottles, so they also need to go. Are there other signs around the house that he might still be in grief?

“Have a talk with him and do it nicely. Is his reason for not removing the items because he is still mourning or that he just got complacent? When Greta passed, her kids removed her clothes immediately, which I appreciated.

“After a year together, your boyfriend should want to make you happy and perhaps he’ll remove those items or have someone do it for him. The clothes could be donated.

“Your question will benefit many seniors who find themselves asking, “What should I do with my ex-spouses or partner’s photos?’

“If your sweetheart refuses, it might be time to re-evaluate the relationship. Does he talk about her often? My feeling is he cares a great deal about you and will move on in his life with you.”

Sue responded, “Thank you, Tom. I just found it so creepy that he hasn’t done the removal himself. We’re going on a trip in July. I asked him if he could please have her things taken care of by then.

“I hope it works because otherwise he is a wonderful, loving and generous man. He did remove his wife’s name and birth/death dates sticker from the back of her old car. But he’s keeping that car as an extra vehicle. He claims he’s over her. Still, I can’t help but wonder.”

There is no right or wrong answer about removing a deceased partner’s pictures or clothes. Everyone has their own beliefs.

Previous comments by Champs on this topic

Ben, a widower, wrote, “It’s been two years since my wife’s passing. My girlfriend has brought up the issue of pictures of my late wife in the house. I am gradually taking them down and moving on in life. Empathy, patience, and love are how I deal with change in my life.”

Cheryl emailed, “I had a boyfriend who constantly suggested that I take down the photos of my late husband. He felt that if I thought it was necessary to have those photos prominently displayed, it meant that I still loved and thought about my husband all the time, and therefore I couldn’t put my whole heart into loving him.

“Eventually, I broke up with him due to his extreme jealousy and possessiveness.”

Kim said, “I will never date another widow because one compared me to the deceased and I was always trying to measure up to a ‘legend,’ at least he was in her mind. Who wants to date someone who can’t heal and move ahead?”

Alicia shared, “Seven years ago, my brother lost his wife of 30 years after a happy marriage. Four years later, he remarried. He still misses his deceased wife. His present wife was divorced for several years and her husband died as well. Both freely speak about their deceased spouses.

“I have learned from them that even though you find someone new who you now love, the past life does not need to be buried. It was a large part of your life and why should you sweep it under the rug?”

Curtis, “I had a sister who married a widower. They were in love and had pictures of both their former spouses around. They talked with each other about adventures they had with their previous families. When my sister died, she was buried with her previous husband, and when the widower dies, he will be buried with his first wife. In the meantime, they enjoyed each other’s company. Both families accepted the other and were glad they had been happy again.”

Sherrill, “My guy Matt loved his deceased wife dearly, and until we met, he believed he would never love again.

“When I moved in with him, Matt asked if I would object to him putting some pictures of his ex-wife on the refrigerator along with my pictures of my kids and grandkids. I had no objection. I felt secure in our relationship and his love for me did not feel threatened; I admired his loving devotion to his wife.

“He inadvertently put pictures of her directly in my line of sight, so I saw them every time I opened the refrigerator door. Initially, this didn’t bother me, but eventually, it did! I asked him if he would move the pictures to a different location on the refrigerator, which he willingly did. He has pictures of his wife and me in his office.

“This is a complicated issue for which there is no simple or right answer. As seniors, we all bring baggage into a new relationship.”

Bill, a widower, emailed, “What matters in the conduct of a new relationship is the acceptance by a new partner of the nature and profound depth of the widow or widower’s prior relationship.

“Confidence is best created when the widow or widower provides an atmosphere that enhances the strength, convictions, and independence of their new loves. Removing doubt and fostering self-confidence minimizes any propensity for rivalry with departed spirits.”

Lynne wrote, “Don’t expect the surviving spouse to ever give up loving the deceased spouse. If not for death, they would still be together. Someone who wants a relationship with a surviving spouse is going to have to realize that there is memory lingering there and be comfortable with that.”

Hopefully, these sensitive replies will help widows, widowers and non-married partners who face this understandable dilemma. There is no right or wrong answer about removing a deceased partner’s pictures or clothes. Everyone has their own beliefs.

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.

Responses to senior first-date jitters

Tom Blake Columnist

May 16, 2025

Responses to senior first-date jitters

14 Champ Responses to Bill’s first-date jitters

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.

See link to that Bill Haley song below.

https://www.bing.com/videos/riverview/relatedvideo?q=bill+haley+and+his+comets+thirteen+women+(and+only+one+man+in+town)&&mid=4A5C77E7FCCDE0DE7C444A5C77E7FCCDE0DE7C44&FORM=VAMGZC

A Senior Man’s first-date jitters

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.

Senior dating sure has its challenges.

Is 83 too old to date?

Are children affecting your relationship?

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.

8 Champs Speak

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.

For additional information or to register: https://tinyurl.com/4fwkbsvm

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.

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