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.
On Life and Love after 50 