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.

You Talk Too Much

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.

Sea of Photos

On Life and Love After 50 eNewsletter – August 9, 2024

Tom Blake Columnist and Senior Dating Expert

In last week’s eNewsletter, Scott, a man in his 50s, asked if he should be concerned when he saw “My True Love” on his widowed girlfriend’s cell phone. It was her deceased husband’s number. Several Champs shared their opinions.

Jane emailed, “My first thought when I read this was what a sweet response the woman gave to Scott when he saw ‘My True Love’ on her cellphone, describing her husband before he passed away.

“She could have said, ‘Yes, he was my only true love’ but instead she said, ‘I’ll have to come up with another name for you.’

“I am a very nick-name-kind-of-person. Giving someone a special name to me means they are loved and have a place in my heart.

“I hope Scott can get past his insecurity. His woman sounds like a keeper.”

Tom’s comment: Jane makes a strong point about nicknames and affectionate terms we create for people we love and care about. I use “Speedo” as Debbie’s nickname, and she uses “Myrtle” as my nickname. Always stated with a smile.

Alicia, “At my age, 72, it will not be surprising that I may come across this situation myself. It was a good refresher for me to see one of the responses you posted about my brother.

“Update on him: he and his 2nd wife were married for a couple of years and divorced. He continues to say he can’t wait to join his first wife in heaven and still cries for her. 

“He is the type of man who doesn’t want to be alone, he has a new lady friend. It’s his life and I want him to be happy. 

“She told him she was not interested in a serious relationship and wanted no physical benefits. He continues to do handyman favors for her and is willing to pay for trips and dinners. Well, at 74, he needs to live his life his way. He says she is fun to be around, so at least he’s enjoying himself. 

Tom’s comment: “Trips and ongoing dinners with no benefits? I’m guessing but I imagine some of our men Champs, including me, won’t go for that arrangement. However, as men reach 70, some might accept the senior no-sex aspect.

Jim, “The reader in last week’s eNewsletter who stated ‘just move on’ probably had a divorce which is much different than having a spouse or mate pass away.

“Many widowed people usually think more about their past love than divorced people think about theirs.”

Leslie (name changed by request), emailed, “I dated a very nice widower after my divorce, whom I met on Match.com. He treated me well, was funny, and was very smart.

“But upon visiting his home he had a wall-to-wall shrine to his dearly departed wife. The focal point was a HUGE portrait of her, with smaller photos bedecking every flat surface. 

“I. Just. Couldn’t. I understand his attachment. It must have been a horrible loss for him when she passed. But visiting him was a total immersion in a sea of photos, mementos, and ephemera. 

Tom’s comment: I admit I had to look up the meaning of the word ephemera. It’s a noun meaning things like old papers, letters, and boxes that are meant to be used for only a short period and then can be tossed away.

Also, I liked Leslie’s “sea of photos” reference. It made me think of a 1958 hit song by Don Gibson, called “Sea of Heartbreak.” It’s an oldie but goodie, the link is below.

Leslie continued, “I quit seeing him because it was obvious that he needed more time to grieve for her. I have enough friends already. I wanted at least an available partner. 

“He is not a “Match” for me, I’m afraid. I’m not saying that the place should be stripped of all evidence. But I AM saying that it takes a special person to be ok with dating in what is, essentially, a museum of constant reminders of how perfect this past spouse was. That’s great, but it’s not for me.”

Bruce, “I will always have some mementos of my deceased wife in my home for my kids to see, if for nothing else. It is what it is as far as I am concerned.”

Christine, (expert dating and relationship coach), “I have a divorced client who is dating a widower and saw a FB post that called his widow the love of his life, and my client called me before she said anything to him. I was sympathetic to how she felt. Non-widowed people often have this feeling.

“I explained ‘she isn’t here’ and ‘can’t come back’ (like her ex-husband) and confirmed how he treats her.

“We also talked about what a loving man he is to her and part of the reason is because he loved his late wife so much. She returned to the man and told him she adored how much he loved his late wife and how proud she was to be with a man who posted such a loving message to her on FB.”

Tom’s ending comments

We all grieve differently. Having photos and mementos of a deceased spouse or loved one is natural. Everyone I know who has lost a special person has photos and other memory items in his or her home.

When we start dating again, we will remove some of these items but not all. Potential new partners must be prepared for those items and accept them. Losing love can be a “Sea of Heartbreak.” And finding love again is a compromise on both sides of the fence.

However, as Leslie stated above, if the new person’s home is a shrine to their deceased love, they are likely not ready for anyone else to enter their life.

Link to Sea of Heartbreak:

Sea of Heartbreak

3 things to avoid after age 70

On Life and Love After 50 eNewsletter

March 18, 2022 eNewsletter #11

by Tom Blake

Three things to avoid after age 70

A couple of months ago, an email from Quora.com popped into my inbox. I had never heard of Quora. I checked it out and discovered that Quora posts multiple blogs on multiple subjects by multiple people.

I signed up to receive Quora’s posts about life and aging. Many of the posts I’ve read so far have been interesting and informative. One post by an author named Doug Armey caught my eye. It was called: What three things should a person avoid once they are past 70 years old?

Armey is likely in his late 60s or early 70s. Regarding his age, he was a bit evasive: “I’m north of the 10th anniversary of my 50th birthday. Somewhere, I’m just not sure.”

Because Armey’s topic was similar to topics we discuss in this eNewsletter, I read his post.

I do not agree with many things he wrote in the article. But, a few of the points he made were helpful. Armey wrote:

First, acting old. Most people hit 70 and suddenly start acting old. They eat early-bird dinners. They don’t drive at night. They can’t go for a long walk. They’re retired but can’t return phone calls. And pretty soon they start looking old and walking old.”

Whoa, hold the horses. I disagree with that paragraph. It’s simply not true. Most people don’t suddenly start acting old after age 70. Perhaps a few people may gradually appear to be aging, but not suddenly unless it’s because of a health issue. I know a lot of people ages 70 and older, into their 80s and 90s, who don’t act old. Their bodies may slow, but that’s not acting, that’s reality.

I’m surprised that Armey didn’t mention that many health issues are beyond a person’s control. For example, heart attacks, strokes, and cancer. People who encounter health issues aren’t acting old or looking old on purpose. Often, when a health issue erupts at any age, not just after 70, it’s unexpected and out of the blue. That’s not acting old. Those are the cards with which we’re dealt. And we cope with them the best we can.

And then Armey wrote this: “Instead, forget about your age. Do everything you should have been doing at 40 to stay in good health. Then keep doing all the things that you used to enjoy and slowly gave up. And most of all stop acting old and looking old. Seriously, it’s not a good look.”

Yes, there are some things we can do such as wearing clean, unwrinkled clothes, shaving, getting our nails done so that when we venture out, we look nice.

 And then Armey wrote about the second thing to avoid after 70. He stated:

Second, thinking old. Most people hit 70 and mentally give up. They retire so they can do, well, nothing. They spend hours watching mindless TV and then can’t remember what was even on. As well as what they walked to the bedroom to get.”

Once again, I object. Especially to the sentence, “Most people hit 70 and mentally give up.” That’s not true. Perhaps a few people but not the people I know. This guy Armey doesn’t know our Champs. Single women in their 70s driving solo across the country or towing an old trailer to San Clemente from British Columbia. Women in their 70s on standup paddleboards and walking briskly in the Harbor. And playing pickleball. Others doing horseback riding. He’s preaching to the wrong group of 70-year-olds.

And how about those who turn 70 and decide to work five more years? Hell, I worked at making sandwiches until age 75.

Armey continues with point number two. “Instead, keep your mind active. If you have a job you like keep working. If you retire, then recreate your life into something meaningful. Oh, and turn off the TV. Believe me, you won’t miss anything. And you might just start remembering stuff like what was in the bedroom.”

I agree pretty much with what Armey said about keeping your mind active. My mom Fran was an avid reader. At age 95, she moved into a bigger home because she wanted more room to store her books. She was a NY Times crossword puzzle expert. Her final bridge game was at age 98, one week before she passed away. At 91, she bought a new car and drove it until 95, when her doctor made her give up her driver’s license, which of course, she wasn’t happy about. 

I keep writing my eNewsletters and newspaper articles because I love doing it and doing so helps keep my mind active. Most important, however, it keeps me interacting with people, particularly you Champs.

As far as turning the TV off, Greta and I have the TV on for maybe two hours a day. It’s usually David Muir news at 6:30 p.m., then Jeopardy, and then YouTube TV streaming music like the Bee Gees, Rod Stewart, Abba, and Bob Seger (that’s what we were watching in our 40s and 50s).

Note to Armey: I know what’s in the bedroom, it’s a doggone bed!

Armey’s third thing to avoid: He wrote: “Speaking old. Most people hit 70 and start talking old. They’re always saying, “Oh, I’m too old for that. Or constantly telling you about their aches and pains and how old they feel. And you know what, as they constantly remind themselves, they start believing it.”

Tom’s comment: Contrary to what Armey saysmost people who hit 70 do not start talking old. He states, “They’re always saying…” something about how old they are. Again, that’s not true. Yes, occasionally, people growing older are going to mention something related to aging, but most don’t dwell on it.

When my Paddle Board buddy Russell, and I talk while paddling around Dana Point Harbor, dodging great white sharks, sea lions, pelicans, and dive-bombing seagulls, we occasionally mention doctor visits and the meds we take. (see a photo of us on our paddleboards below).

But we also talk about yachts heading out of the harbor at 10 knots per hour when five knots per hour is the posted maximum speed limit, (and the signs on buoys also state “no wake,” which means slower than five knots, particularly for larger boats). When boats make a wake, most paddleboarders must turn into the wakes, to avoid being hit broadside by a wake that could dump them into the water.

During our 40s, we would have flipped off those speeding boat captains and yelled some profanity at them. Guess what? We are tempted now as well, to get them to slow down. But we usually don’t flip them off or yell. 

On the third point above, Armey added, “Never utter the words, ‘I’m old.’ I don’t care how old you are. And purposely forget when you were born so you can’t remember your age. Then do the things you like and never speak of age again. You’ll surprise yourself and frankly shock others. It’s fun.”

He added, “A friend of mine, who is a bit older than me, has a bumper sticker on his BMW M5 which says, ‘Growing old is mandatory, acting old is optional.’ You’ll age successfully but only as you purposefully forget your age.”

Tom’s comment: How can we forget when we were born when we are asked for our date of birth whenever we have a medical test or medical appointment? If we say, “I can’t remember.” That’s acting old.

Besides, how can I forget my age when my favorite singer, Bob Seger, keeps reminding me in his song, “Like A Rock,” which pops up often on our YouTube TV music channel at night apparently because it’s on our favorites list?

In that incredible song, Seger sings, “20 years now, where’d they go. 20 years, I don’t know. Sometimes, I sit and wonder, where they’ve gone.”

I sing back to Seger, a fellow Michigander, “80 years, where’d they go, 80 years, I do know.” I’ve been blessed beyond belief. Most of my memories are as vivid today, as they were when they happened. I recall them. Like A Rock.”

So, when you hit 70, here’s what you need to do. Point to the sky and say “Thanks. It’s been a great run; I’m ready for more. Like A Rock.”

Link to Like A Rock

Link to Quora