senior dating tips – On Life and Love after 50

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 5^th 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.

Senior dating: Who Pays for the Date?

On Life and Love after 50 eNewsletter
August 11, 2023?
Who Pays for The Senior Date By Columnist Tom Blake

Who pays for the senior date?
The man, the woman or do they share?

An email from a long-time Champ inspired today’s eNewsletter.

Cheryl wrote, “I’m 68 and gave up on dating, especially online, because I was getting a lot of overseas scammers and I also experienced a group of men who were classless, meaning, they were cheap.
“I don’t need anyone to pay my way, but in my life, I’ve experienced people who have the means to treat me to the niceties of life and were happy to do it.

“I’m always surprised that women say if a man pays for dinner, the men expect something else, (like a roll in the hay)-so crass. I’m not sure what to think about men who don’t at least buy a drink or a light meal that might make a nice impression. If they don’t, am I to think they might be frugal and the rest of my life with them will be lacking in the things that I enjoy?”

Tom’s response to Cheryl: “I always pay. Sometimes a woman will strongly insist she pays for her own expense on the first date. And if I don’t let her, she will be offended so I let her. However, I’m old-fashioned, I’m very casual when the bill arrives. I’ll break her hand if she reaches for it. That’s how my parents raised me.

Cheryl responded, “I’m glad you shared with me that you pay. I’m not a feminist and also have old-fashioned values even though I have been a businesswoman and savvy real estate and stock investor (only saying this because some of us women are financially stable and not looking to take advantage of men). I guess there’s a group out there who ruins things for everyone.”

This “Who Pays for the Date?” issue has been a concern in senior dating for years. In fact, I wrote and published an ebook titled, “Who Pays for the Date?” in 2009.

In thinking about Cheryl’s “Who Pays” question this week, I went to Smashwords, my online ebook bookstore (the second largest ebook bookstore in the world after Amazon.com), and reread my book.

Humbly I say, it’s a wonderfully entertaining 16-page book and right on the money (pun not intended). Very little has changed in 14 years. I’m offering it to you Champs today for $1.99 (remember it’s an ebook, not a printed book). Most of what I wrote still applies today. See the link to the book at the end of today’s eNewsletter. Here’s a short excerpt from my 2009 book about my personal friend Buddy.

“Since Bobby and the woman were meeting in her neck of the woods, 15 miles from where he lived, he asked her to select the restaurant where they would meet. This was Buddy’s first mistake; he was no longer in control of where he’d be spending his money on a woman he’d never met.
“Early the next morning after their first date, the e-mails started flying my way. Buddy wrote, ‘Nicki has expensive tastes! I would have preferred a coffee shop, but what could I do after I was at the expensive restaurant?’”

Lesson learned. Buddy was foolish for asking Nicki to pick the meeting place. Since he initiated the date, he should have taken control and suggested coffee in a less expensive place. When men are paying for a first date, they shouldn’t give the woman carte blanche to choose where to meet. If a woman offers to pick the place, the man should say, “Thanks for the offer, but I want our date to be special, so I’ll choose the place.”

Champ Jim said, “I think men should pick up the tab on the first few dates and share the costs occasionally after–if the women financially are capable to help. The women don’t need to pick up the bill but going Dutch or at least offering to pay is a start. Some women expect the man to pay it always and never offer to help.”

Tom’s comment: Two weeks ago, I agreed to meet a woman who lived 30 miles away. I was going to her city on another project so I figured I’d multi-task: complete my project and meet a nice new person I’d met online. We agreed on 3:30 p.m. for coffee in her city. I asked her to choose the meeting location. She mentioned a restaurant. I didn’t check on it online, but soon found out it was an elegant, high-class, expensive French restaurant.

My drive to meet her, which normally takes a half hour, took two hours due to traffic problems. So, I needed a glass of wine, not coffee. When I got to the restaurant, I was seated outside at a patio dining table. The woman arrived a few minutes later. Instead of coffee, we each ordered a glass of wine.

Since the restaurant was empty, a waiter kept bugging us about ordering appetizers or an early dinner. I wasn’t hungry; she was. She ordered dinner, fresh sea bass, caught locally. I had a Gazpacho appetizer: $14.00. The bill for our wine, her dinner, my soup, and the tip was $162.43. I paid without batting an eye but cursed at myself for letting this happen.

Lesson learned. Going forward, I will designate the place and that our first date is for “coffee only.”

Three days later, I met a nice woman at a coffee shop near my home. When I got there, she had already bought and paid for her coffee. I got a coffee for me: $3.29. We had a delightful time.

Also in 2009, I was a columnist for The Orange County Register. I quoted an article I had read titled, “Courting Costs Are Yours, Too, Ladies,” by humor columnist Amy Alkon(www.advicegoddess.com). Amy wrote: “If a woman considers herself a man’s equal, her equality shouldn’t evaporate when the check comes. The point here isn’t calculating each person’s outlay to the bent dime. Just that dating shouldn’t send men to the bankruptcy court and women to the mall.”

In that column, I added, “Men want to see a little jingle come from the woman’s purse to help contribute to the exorbitant cost of dating.”

Tom’s 5 tips in 2023 on who should pay for the senior date

1 On a first date, the man should almost always pay. No matter if the woman wants to pay her half. However, the man should designate the place to meet and the time, and always specify, “coffee,’ whether he or she drinks it or not. Optional: tea. And the man should designate the place if he initiated the date.

2 On the second date, the man should also pay. UNLESS she suggests a pricey outing. If that’s the case, I feel the man needs to step forward and say something like, “That’s a bit out of my budget. I just paid my daughter’s Harvard University tuition and I’m on a tight budget now” (or some similar flimsy excuse).

3 If two seniors become a couple, on the third date and going forward, a discussion on “Who Pays?” needs to happen soon. This is where love, understanding, caring, and sharing enter the picture. Communication takes over, a key to senior relationship success.

4 When the woman is more comfortable financially than the man, they need to lay the cards on the table and work out an amenable arrangement. This is where fairness and a willingness to compromise enter the scene. And that may enhance the longevity of the senior relationship.

5 If he always pays, she can equalize things by cooking him dinner at home.

Link to Smashwords, the eBook bookstore:

Link to Who Pays for the senior date?

Why didn’t John ask for her phone number?

On Life and Love after 50 eNewsletter

July 8, 2022

By Tom P. Blake

23 responses to “Where is John?” eNewsletter from July 1, 2022

Last week’s column was titled, “Where is John?” Champ Yoko and prospective Champ ‘John’ spoke for 2 ½ hours at the Swallows Inn, a popular San Juan Capistrano watering hole and country music hangout. But, why didn’t John ask for her phone number? I asked for your comments re: what should have Yoko done?

23 Champs shared their thoughts–21 women and two men. That’s about a 9.5-to-one ratio, which is about par for the course in senior dating age 65+

23 Responses

Althea, “Was he married? Or, just out with his friend to have a good time. Perhaps he “Just Wasn’t That Into Yoko.”

Melanie, “John is married, or has a girlfriend, or just enjoyed talking. Yoko can’t bother herself about the reason…John didn’t want to go further.”

Sandy, “Some men carry baggage from previous relationships and/or use bars as their social outlets to get their social fix.”

Patty, “He was not wearing a wedding ring. That or showing pictures from his phone that show no women is no indication of whether he is married.”

Terri, “Yoko should realize that ‘John” has either a wife or a girlfriend and he just found it pleasant to hang out with her and her friends and nothing more. Done. I have personalized business cards with my name, email, and phone number, should the need arise.”

Teresa, “It seems risky to begin talking to an unknown person in a bar. Everything this guy said could be a lie. He could be looking for a woman with money.”

Thyrza, “His showing off his property would not bode well with me. Men show off their chivalry, that’s all it was. Put it to rest.”

Victoria, “Yoko’s story is as old as time itself. He’s probably married or in a relationship. The lack of a wedding ring is not foolproof. Perhaps he decided a relationship with her wouldn’t work.”

Joel, “I learned, as a matter of courtesy. Just to tell someone, ‘I don’t think we are a good fit’ and to accept it when someone (many in fact) have said something similar to me. You have to click with the person. Say ‘Next’ and move on. It’s not you, Yoko, of that, I am sure.”

Maria, “Maybe Yoko should have said, ‘Would you care to meet sometime and continue the conversation? At least she would have gotten a clearer picture of where he stood. She should chalk it up as a fun evening.” (comment from Tom: should-a, would-a, could-a) hindsight is always easier).

Larry, “Yoko did all the right things and enjoyed herself. Any loss was his loss. Yoko, keep on keeping on!”

Anonymous woman, “It can take time for a woman to see that a rebuff may have zero to do with her. When that is figured out, it takes a lot of pressure off.”

Elenute, “If a man wants to contact a woman, he will find a way. Yoko should forget about him, attractive though he may be.”

Wayne, “Yoko should have simply stated at the end of the encounter: ‘John, I enjoyed meeting you and would like to see you again. Let’s exchange contact information. If he accepts, great. If not, it’s a red flag.”

Sue, “If John wanted her contact info, he’d have asked for it. He had a nice night and that’s that. Unfortunately, ‘He wasn’t that into her.’

Susan, “Suggestions for Yoko if the situation arises again:

“As Tom suggested, give him your card with contact information.

“Say: ‘I would like to visit your farm, let me know when a good time would be. Here is my number.

“Or, ‘I’m having a BBQ soon and would like to invite you. What would be a good number to reach you?’”

Gail, “John was a player. Yoko, count your blessings and be glad you dodged that bullet. It has happened to me. The guy wasn’t that into me. Fine, who’s next?”

Bonnie, “I learned a great lesson about guys through my oldest son. He and a girlfriend hit a bump in the road. He went through remarkable lengths to renew the relationship. I learned firsthand, that if a man wants to pursue a woman, he will just do so. He doesn’t overthink it. He just courts her naturally.

“Yoko might bump into him in six months, and they pick up where they left off. Timing can be a big deal.”

Heather, “I have a history with the Swallows Inn San Juan Capistrano. My brother Doug was a bouncer there in the 1960s. I really love a seedy bar. What’s funny, I met my significant other, Reuben, there. He has a horse at a stable down the road and came on Tuesday’s when Pedro makes tacos in the kitchen.

“My friends were my ‘wingmen.’ When Reuben would enter the bar, they would coax him over to sit at our table. Once, he grabbed my cellphone and put his number in my phone. Our first date was April 1, 2017. We’ve been together since.

“I wish Yoko had pushed a bit more or returned to the Swallows on the same day the following week. Life is too short for missed opportunities.”

Cheryl, “Has it happened to me? Yes. I’ve had many men tell me how busy they are right now, or what emergency has come up in their lives, that I don’t even pay attention, don’t care. The ball is in his court. My late husband would have driven to the moon to ask me out again if he had to.”

Kaitte, “Happened to me? Yep, for a split second at a gas station. He kept looking at me after he let me in the checkout line for gas. I was at the pump, and he looked around and found me. I should have given him my INTRO card. By the time, I figured that out he was gone. I did post lookout on Facebook but no response. Sigh, I’m 70, those vibes don’t come around often.”

Marie, “I have known friends who already plan weddings after an initial encounter and somewhat naively expect a positive follow up after they have enjoyed themselves. I have had men tell me after a first date that I am everything they are looking for…after knowing very little about me. Presumptions are not limited to the young folks.”

Marjorie: “I agree with Bonnie and my personal experience: If a guy is
interested he will make it happen. Otherwise, as others have said, he is
married, has a girlfriend, or isn’t that interested. Of course, she can ask
about meeting again, but take whatever he tells you as the answer. Don’t chase
him. And more important, don’t settle for being someone’s alternative.”

So, that’s it Champs. I know Yoko personally; she will relish your advice. And, chances are, your advice will benefit lots of other single women who go line dancing our just out for pizza and they meet a guy.

Senior dating tips. Four ways for seniors to meet a potential mate during the pandemic

On Life and Love After 50 eNewsletter January 21, 2022

2022 eNewsletter #3

by Tom Blake – Columnist

Senior Dating tips. Four ways for seniors to meet a potential mate during the pandemic

Champ Sonia (see her picture above) emailed that she wants to date someone her age or younger. She wrote, “I’ve read your eNewsletters for several years and I love them. I am 63 and would like to date someone my age or some years younger.

“You are so far away from me, but I would love to participate in one of your Meet and Greet sessions but I don’t know how to do it because of the distance and now the situation with the new covid.”

Tom replied, “Thanks for writing, and thank you for being a Champ for several years. I understand your frustration with the Covid situation, which is affecting senior singles not only in PA, where you live but across the world.

At 63, you should normally be able to meet eligible men within your dating age range (even younger), but Covid has thrown the proverbial monkey wrench into the search.

Even the Meet and Greet sessions you refer to at Tutor & Spunky’s, my former deli in Dana Point, California, have been on hold for two years now. So, don’t get on a plane or a train to come to the Meet & Greets—all you could meet would be meat—as in a pastrami sandwich–for example.

So, you’d be wiser to try to meet someone closer to you in PA or adjacent states, someone who would be within reasonable driving distance. How to do that during the pandemic? In four ways:

1 Try senior online dating. You won’t even need to wear a mask while you’re online. Our November 19 eNewsletter was titled, “Which online dating site is best for seniors?” I’m not an internet dating expert. So, I quoted our Champ Christine Baumgartner, an expert dating and relationship coach. Christine lives in Orange County, California, and calls her business “The Perfect Catch.”

Here’s what I wrote on November 19, 2021 in an eNewsletter, which is on this website.

“When Christine is asked by a client which dating site is the best one, her reply is, ‘This may surprise you. They’re generally all the same.”

To read more about senior online dating, go to Christine’s Facebook page. She’s got great material on there. Or to her website (the link is listed below). Use a site that caters to seniors such as Silver Singles or OurTime (owned by Match.com). Most sites will charge a monthly fee. POF (Plenty of Fish) doesn’t unless you upgrade, but it has a reputation for having scammers.

And speaking of scammers, be careful no matter what online site you choose. There are scammers on every site. They prey on lonely seniors, primarily widows, so there is a risk in online dating. But, by going online, you’d be able to establish a reasonable search radius, say within 50 miles of where you live in PA

2 Get off the couch and out of the house when the pandemic eases. Still take precautions—wear a mask, meet people outside when possible, keep social distancing. If you see a man who appears to be single—no wedding ring, for example—and he appeals to you, be assertive by saying hello or ask him a question like, “Which wine goes best with this salad?”

Be assertive, but not aggressive. When senior singles venture out and embark on a new activity, their chances of meeting a potential mate increase. Here’s a story I heard this week, while on my Stand Up Paddleboard in Dana Point Harbor, of all places.

As I was paddling from shore, a guy on his board yelled, “Hey Tom, I attended several of your Meet & Greets and enjoyed them.”I said, “Did you find a mate there?”“No,” he said, “but I learned from what you often said to us–to get involved in activities we enjoy. So, I took ukulele lessons and met my partner there. We have a lot in common. Thanks for the advice and for having those events.”
I never thought I’d hear a success story like that on a paddleboard! Also, volunteering is a wonderful way to meet people and to pay it forward as well.

3 Network. Ask your friends, co-workers, and acquaintances if they know of someone who is near your age and single and who might be a nice mate for you. And don’t stop asking because as we age, people’s lives change. Some become widows or widowers, and others have relationships end.

4 Attend outdoor classes (when the weather is warmer) such as tai chi, yoga, pickleball, ukulele (or other instruments), and on and on.Bottom line: Make yourself as visible as possible and work on your appearance through exercising and eating right to help you stay healthy. Keep your expectations in check. Don’t go out with the express purpose of meeting a mate.

Instead, go out to enrich your life. Be friendly, have a positive attitude, make yourself likable. Don’t give up hope. We are all in the pandemic challenge together. Be very careful with exposure to Covid and be leery of scammers. I hope we are all vaccinated and boosted.

Keep the emails and questions coming. We have some interesting upcoming eNewsletter topics, including how to deal with a long-distance relationship during the pandemic and even details of a conversation I had with Johnny Cash regarding words Johnny said to me after we left his recording studio together in 1976.

I had co-produced a record album with him at the studio. So, stay tuned, stay safe, and keep on truckin.’

Sonia shared her photos with us today. If male Champs would like to contact her in PA, email me and I will forward your email to her. You never know, you just might have interests in common with this nice woman.