romance – On Life and Love after 50

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

Responses to “You Talk too Much (on a senior first date)”

On Life and Love after 50 eNewsletter – February 28, 2025
By Columnist Tom Blake

Responses to You Talk Too Much (on a first date)

First date etiquette

There were multiple responses to last week’s eNewsletter about Susan’s claims that men talk too much about themselves on first dates. Thirteen (4 men, 9 women) responses appear in today’s column.

Rhonda, “Although I’m older (68), I have a lot in common with Susan, and I have also been following you for many years. I, too, have been on my own for 12 years and am disenchanted with online dating. I’ve tried different platforms, as you suggested, and even spent money on eHarmony for a full year.

“I was told it’s the best senior online dating site–expensive but worth it. It didn’t work that way for me – people from way out of the area and a few dates here and there who, yes, talked almost exclusively about themselves.

“As much as I tried to talk just a bit about me, it seemed like the man would dial back to something about HIM. It’s fairly apparent when someone doesn’t seem very interested in what you’re saying, and off they go about themselves. I have some interesting traits and things to discuss (I’m a triplet, for example), but it just gets brushed aside. Strange.

“Are these guys nervous? It’s possible, but they do seem pretty relaxed. Maybe too relaxed? Ditto for the lack of response when texting sometimes. I will text a hello, a joke, or a little something, and get no reaction but simply a picture of his dinner! Huh?

“Is it possible that many guys in our age group know there are more women seeking their attention, so they become complacent? I wouldn’t tolerate this one-sidedness from a guy who is trying to win me over.

“I am hopeful there must be SOMEONE out there for me so I’ll keep the faith. I volunteer, play Pickleball and am active and fun. I’m trying, but it’s frustrating.

Tom, San Juan Capistrano, “I’m 64, live in San Juan Capistrano, and I’ve been single for 13 years. I ride mountain bikes with a group of very friendly, mature people. I’ve learned how to socialize better and communicate since joining the group. It’s helped me take an interest, ask questions, and listen to what a person is saying. This helps me relax on a date.”

Marianne, “This is the first time I’ve replied to your eNewsletter. I’ve had the same experience as Susan. I have been on over 30 dates using Match.com and all the men talked about themselves incessantly on the first date. They may be nervous. However, I think they treat the first date as a job interview because they really don’t know another way to have a conversation.

“It’s disappointing that men our age lack the skills to carry on a mutually stimulating conversation on a date. I have done what Tom suggested and interrupted to make my own comments about what he has said, or I’ve bluntly said “My turn” with a smile.

“I always speak to a potential date on the phone first, and the conversation flows easily. It is puzzling why it is more awkward for men in person. Perhaps, in-person conversation skills are a lost art because of texting, which everyone seems to rely on these days. Texting your thoughts is a one-way conversation that doesn’t’ require sitting in front of a real-life person looking into their eyes for understanding or acknowledgement.

“My advice for Susan is keep going on dates and understand that your dates may be nervous. However, break into the conversation and talk about what you are interested in, and see how the conversation goes from there.”

Joanie, “Tom why don’t you start off with 10 questions to ask on a first date to try to get to know someone? Many folks talk too much about non-meaningful subjects (their new car, what trips they have been on, etc.)–subjects that don’t contribute to getting to know each other. So, the relationship never gets off the ground.”

Cheryl, “Champ Susan is spot on with her why men don’t ask questions! I have been dating for 20 years. I am a great conversationalist, have a good sense of humor, and am educated and attractive. Yet 99% of men talk about themselves during the entire date. I’ve asked men, ‘Do you want to know anything about me?’ Often, I must push my way into a conversation and say something about me that’s pertinent to what he’s saying.

“Sometimes I articulate clearly, but humorously, something like, ‘I hope we’re not going to spend the entire time talking about Medicare!’ I have tried everything, and the result is always the same: the man goes right back to the subject he was talking about (himself), as though I hadn’t even spoken. There is NOTHING amiss about Susan. It’s the men who need help.

“They never learned the art of conversation, or the etiquette involved. They’ve never learned how to be genuinely interested in a woman’s life. Mostly, they are busy wondering if they are going to get sex tonight or if they’re wasting their time with me. They are simply not present on the date.”

John, “I agree with Susan about finding the right prince who understands balance in conversations, as you pointed out so she could share her experiences, views, and perspectives on things with a potential mate.

“Asking questions about each other leads to information to build upon for compatibility. I hope she eventually finds the right prince among us frogs, especially in a nice area like Dana Point.

Belinda, Ajijic Mexico, “Like Susan, I’m 63. I’ve had several long-term relationships and a 22-year marriage over the last 45 years. I spent six years on Match with no dates. All the men I expressed an interest in did not reciprocate my interest. I met two guys on EHarmony. Neither were right for me. Zoosk had better results for me as far as the amount of men to meet, but because it’s a free service (or was), there are a lot of ‘questionable’ men on the site: Married, Nigerian Scammers, etc.

“Same problems on Facebook, Yahoo, and especially on Plenty of Fish. I spent years searching actively and I finally gave up. It will need to happen organically now, if it happens at all. Tell Susan I’ve also had those dates where the men just run off at the mouth about themselves and never want to know anything about me. It’s exhausting. I wish her well.”

Joel, 80, newly widowed, said, “Having spent years on Match.com up to 2012, finding the perfect mate, getting married and then widowed, I’m back as a widower in 2025.

“What I heard back then and hear now from women is that many, if not most, of the men they meet are like the ones Champ Susan met. They spill their guts and don’t seem interested in her.

“Knowing this, I go into an interview (a first meeting is NOT a ‘date’) with questions based on what a woman’s online profile says. A recent prospect told me many things about her life, wishes and hopes, her politics, her activities, etc. We talked for 1 ½ hours.

“She told me I was unusual, special, and that I would be very appealing to any women I meet because I ask questions. She said she had never met a man so interested in her. I was encouraged. In my follow-up phone call, she said she wanted to ask me questions because she was taken aback.

“She said, ‘I was so caught up I didn’t think to ask you about anything.’ I said, ask away, and she did. Turned out she either wasn’t interested in me or, maybe, anyway, at this point, so I told her to let me know if she changed her mind.

“Men will do much better if they learn about active listening and go into any first meeting with a prospect armed with questions and the desire to get to know her. You will stand out as unusual and you will learn enough to decide whether to go forward. “Here’s good place to start developing a new approach (this will work for women as well): https://en.wikipedia.org/wiki/Active_listening

Julie (in Florida), “I found Susan’s email and your response both fascinating and thought-provoking. Your point about the men possibly being nervous is well-taken. The pressure of a first date, especially in the context of online dating, can be incredibly daunting. However, I also wonder if Susan’s own approach might inadvertently contribute to the one-sided conversations she’s experiencing.

“Your suggestion of a therapist is excellent. Exploring potential communication patterns or subconscious expectations could provide valuable insights. It’s also worth considering that the dating landscape has changed dramatically, and Susan’s experiences might reflect the challenges inherent in online interactions – the lack of immediate nonverbal cues can make it difficult to gauge genuine interest or build rapport.

“I especially appreciate your new “Ask the Therapist” feature – it’s a wonderful addition to your newsletter.

“My own experience, at 73 and recently widowed, mirrors Susan’s apprehension. The dating world feels vastly different now, and the added layer of online scams presents a real concern.

“Navigating this requires a balance of cautious optimism and self-awareness. Perhaps Susan could explore alternative ways to meet people outside of online dating, focusing on activities and social groups that align with her interests. This could lead to more organic and authentic connections.”

Shelley, “Susan is correct. Most men at this age talk about themselves and are only thinking about their agenda. Maybe they are trying to impress us but just want the prize with no investment in who you are as a person. They just need attraction and a nice smile from you. Very shallow. I’ve gone on plenty of dates and know this to be true.”

Dee: “Susan thinks very highly of herself and likes being single. She doesn’t really need a man. She knows (not thinks) she’s gorgeous from her self-description. Perhaps she comes off to the men as I saw her; self-absorbed. Good luck Susan and all those lucky men who she chooses to go out with.”

Jackie, from Georgia, “I remember being on a dating site and the guy called me and talked nonstop for 2 hours. WHY I stayed listening was beyond me with his comment – “Next time you can do all the talking. I was too worn out to want another time to talk. He called one time and said, ‘Oh, the wrong Jackie!’

“I agree with you that getting out and especially enjoying Dana Point. The Harbor is inviting. Who knows who you might meet at Costco? My sister and I ran into you there a few years ago.

“I’ve dated four widowers since Randy passed and they only had marriage on their mind. For me, friendship was what I was enjoying. I’d tell Susan to enjoy her freedom! I hope you can help people with your new – ‘Ask the Therapist’ I’ve had my share of counseling in my day!

Elenute “It’s not bad to give people the benefit of the doubt, as you do, Tom. Yes, they might be nervous, etc., but they are also revealing who they are. I’ve dated a lot of men, and some of them really don’t understand that conversation should be a two-way street. It’s very hard to find one who does. Even then, watch out for narcissists.

Comment from Tom: Three men emailed me, asking if I thought Susan would be willing to meet them for coffee. I let her know. And I believe she may have agreed. Remember, I’m not a matchmaker, but it seems that it might have happened this week. When Champs email me, it’s important they include their city where they live and their approximate age.

Ask The Therapist

Dear Debbie, “What can senior men do to prepare themselves for a first date so they don’t talk too much about themselves?

Great question! I’d also include what women can do to prepare for a first date. First impressions matter, so basic grooming—showering, deodorant, flossing, and dressing comfortably and appropriately—is essential. It may seem obvious, but both men and women sometimes overlook these details.

For online dating, I found it helpful to get to know someone through messages before meeting. Texting and phone conversations reveal a lot—sense of humor, availability, flexibility, values, and common interests—all of which can help determine compatibility before agreeing to a date.

Preparation also includes a good night’s sleep, a positive attitude, and being on time. Regarding last week’s topic of talking too much, I often attribute it to nerves. If there’s a connection, I’ll go on a second date to see if that’s the case.

On the date, ask open-ended questions, (e.g, if you could change one trait about yourself, what would it be?  If your best friend could choose an adjective(s) to describe you what would it (they) be?  What does your ideal weekend look like?), make eye contact, and practice active listening. If one person dominates the conversation, try summarizing what they said and asking a follow-up question—this keeps the conversation balanced and engaging.

Debbie Sirkin, LMFT, does not provide any psychological or other health-related services or advice to individuals within the newsletter, and even when responses to questions are answered in the second person as a literary device, they are general and hypothetical, and not intended to be personal for the questioner. Answers are for general information only, and never constitute advice for any individual. Under no circumstances does Ms. Sirkin provide legal advice or medical advice.

A Senior Love Story

On Life and Love after 50 e-Newsletter – October 11, 2024
A Senior Love Story
By Columnist Tom Blake

In August 2021, Ray Freer, 80, a widower, moved from Park City, Utah, where he had lived for 30 years, to Laguna Woods Village, a 55-plus private community of approximately 18,000 residents in Orange County, California.

He moved to Laguna Woods because he loves to play tennis. I was introduced to Ray by my friend and fraternity brother, Tom Brunkow. Tom and I met 67 years ago in 1957, as freshmen in the Beta Theta Pi fraternity at DePauw University, in Greencastle, Indiana.

Tom Brunkow is in the DePauw Athletic Hall of Fame for his tennis accomplishments. Ray has won multiple tennis tournaments and through tennis is how they met.

Ray signed up for my eNewsletter on December 21, 2021. Emails Ray sent me over three years are included below.

Ray’s December 21, 2021, email Ray wrote, “Went to a dance. I found it very awkward. On either side of me were a married woman and that sort of protected me. They were not on the market. Across the table were six unattached women. That intimidated me.

“I play racket sports (Tennis, Paddle and Pickleball). There are lots of attractive women doing that, which makes it easier for me to talk to them one-on-one.  “In Laguna Woods almost everyone is friendly. I haven’t connected with a woman yet. I am sure my time will come. If lightning strikes, I will pursue it wholeheartedly. “Octogenarian (80) Ray of Hope.”

Ray’s April 11, 2022, email Ray emailed “Life here in Laguna Woods is good and getting better. There are quite a few LATs (living apart together couples) here.

“It’s lonely. I haven’t found anyone, but all is OK. The good thing about the activities is they allow a person to meet others with similar interests before getting deeply involved. The activities provide time and opportunities to meet without commitment.

“The demographics here in Laguna Woods suggest seven or eight women for each man. Here’s how I estimated the ratio (the numbers are approximations): The population of Laguna Woods is 18,000. Six thousand are men and 12,000 are women. Assuming 5,000 of those men are married, that takes away 5,000 from the 12,000 women. So, 7,000 available women are left with 1,000 available men.

“Many people have significant others here. Some women, consistent with a lack of interest, just are not available. But that still suggests there are lots of ladies out there.

“It is weird being out there at 81. Many of the women with whom I talk say that the only thing men want is to get into the sack with them but with no real ongoing relationship. Some say it’s not worth the bother. Many simply avoid the dating scene entirely.”

Ray’s October 14, 2022, email “It is just my impression, but when a couple starts sleeping together the relationship becomes more emotional. At some level that implies more of a commitment. “I enjoy senior sex, but I have not been pursuing it because I don’t want to hurt the other person by not following through with an emotional and enduring commitment.

“The other side of that is I am picky so that is frustrating as well. I suspect I am not unique but, ‘Who knows?’

“I have some lady friends that appeal at one level or another, but it just hasn’t reached the ‘Let’s get physical’ stage a la the Olivia Newton-John record. I suspect it will come but who knows when? It’s a conundrum.

“The final issue is, while someone might appeal to me, it does not necessarily follow that I would appeal to her. It wouldn’t be her fault if I didn’t float her boat.

Ray’s February 10, 2023, email “I read your list of 12 characteristics in your eNewsletter. I never made a list of characteristics wanted in a mate, but it makes sense. Also, in concert with your eNewsletter, I have never sought a replacement for my wife Mary. On the other hand, I do seek a person with some similar traits she had.”

“Regarding your question about my involvement with a person here. I am involved with a gal named Libby. Her father taught me how to play tennis She checks off a lot of the boxes on the list. I keep thinking it might come to pass, but so far, no real heat. She has lived in Laguna Woods for more than 10 years.

May 2024 In May 2024, My woman friend Debbie and I were invited to dinner at Ray’s home with the Brunkows in attendance. Ray and Libby had become a committed couple.
Senior marriage at 83

Ray’s September 27, 2024 email “Libby and I married on June 29, 2024. We had lived together for a year and a half. She sold her condo and moved in with me. We have known each other for 74 years. When we were kids, she was a year and a half older than me. When I was in 5th grade she was in 7th, an unbridgeable age gap at the time.

“Now at the advanced ages of me (83) and Libby (84), the age gap isn’t an issue. I refer to her as a cougar robbing the cradle.

“I play tennis frequently. Libby walks daily and I join her three days a week. Both of us go to the gym regularly. We are healthy and that is why we married. We simply want to live those twilight years as positively as possible.

“Your list of twelve questions to discuss to determine compatibility was very helpful. We are so boring. We were similar in answering every question. We appreciate each other and are fortunate to enjoy many of the same things. Your eNewsletter helps many seniors.”

Tom’s comment: Wow, Ray and Libby’s story shows why single seniors should never give up hope. The coincidence of marrying someone he knew for 73 years is mind-boggling. And exciting.

Ray and Libby Freer wedding June 29, 2024

photo courtesy of Ray and Libby Freer