Category: Match.com senior dating

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.

Senior dating: Deal Makers/Deal Breakers

By Tom Blake NL

March 10, 2023

Senior Dating: Deal Makers/Deal Breakers

By Tom Blake – author and columnist

After sitting at home alone for five months after losing, Greta, my partner of 25 years, with the exception of having had a few casual coffee dates, two meals out, and attending some social events, I decided I needed to do more reaching out to meet other senior singles. I had grown weary of listening to Collin Raye’s March 1994 song “Little Rock,” which is one of the most powerful loneliness songs I’ve ever listened to.  (see link at the end of today’s article).

I’ve heard from many seniors who say they’ve met a new partner using online dating sites. On one particularly lonely Monday night, I decided to join Match.com. Here’s what I’ve learned after one week.

There are a plethora of quality senior women on Match. From scanning their profiles, here are a few facts that I consider to be deal makers or deal breakers.

  1. A person’s listed age. It doesn’t mean the age listed is accurate. Someone who posted their profile a few years ago may have subsequently changed their birth date so that the posted age next to their picture is lower than their true age. However, I think most ages listed are accurate. At my age, 80+, lots of people will pass me by for a younger version.
  • Photos. This is huge. Often, but not with everyone, the thumbnail photo on the home page was taken 5-10+ years earlier. So, be ware of outdated thumbnail photos.
  • One needs to scroll through all the photos posted by that person (some people post 10 to 20 photos and more recent photos reveal how a person has aged). You must almost become a detective doing your sleuthing to determine what a person looks like currently. Boy-oh-boy, people can age quickly. I think of Rod Stewart’s song Maggie May, when he sings, “The morning sun when it’s in your face really shows your age.”

Also, some people don’t put captions under their photos that reveal when their photos were taken. They just leave the captions blank. Or they include a caption, for example, that says, “Summer of 2016.” Then you have to say to yourself, ok, add seven years to envision how the person looks in 2023.

Some people post pictures of flowers or of them in restaurants with a bunch of friends with a caption that might say, “Here I am with my women friends in a restaurant in Rome in 2010.” Or they post photos of themselves wearing hats so large their faces are so dark you can’t see what they look like. Many don’t show full-body pictures, so you have no idea of what their bodies look like.

Not to mention. They post pictures of themselves holding their dog or dogs. Or, pictures of the dog by itself. Senior daters aren’t looking to date a dog; they want to date a real-life human being.

  • The next item I look for is political party affiliation. I like to see “Moderate” or “No party affiliation” listed. I don’t want to match up with a screaming conservative or a screaming liberal. I’ve seen profiles that state, “All politicians are corrupt.” Party affiliation might not be a deal breaker in a relationship but two people would need to judge that for themselves.
  • An important consideration is how far away a person lives from where I live. Long-distance relationships are challenging. If a person lives more than a half hour away by car it will be difficult to see each other often enough. I don’t look at a profile if a person lives far in the Los Angeles area. If I ever get into another committed relationship, I’d hope to be with that person four to six nights a week.

One thing I discovered is by widening my search radius by 10-30 miles, I am getting posts from people in the Palm Springs area. That’s important to me as I will be spending a lot of time at my vacation home out there. It would be nice to meet a new friend who lives in the Coachella Valley instead of hanging out in an Agua Caliente Casino looking senior love or for luck.

  • Many women have pets, particularly dogs, and then cats. Some have horses. I don’t have a problem with that. However, if every picture posted shows them with their animals, that can be a turnoff.
  • Online dating for seniors isn’t a picnic or a candy store. It takes effort, time, energy, honesty, decency, patience, and creativity. One needs thick skin because rejection is part of the game.
  • Senior online daters need to remember the adage: “All it takes is one.” And that’s what most senior singles are looking for.

As time goes on, I’ll try to keep you posted on my online dating adventure. Until then, here’s the link to that Collin Raye song. Get your hankies out.