| 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. |
On Life and Love after 50 