I am socially challenged to some extent. I’ve always found it difficult to engage in casual conversations, especially with people I don’t know. Coupled with weak small talk skills, the result has often been awkward and discouraging. Since retiring, I’ve made it a priority to work on this weakness by developing better coping strategies and conversation techniques. I’ve been using ChatGPT to assist me, and I try to practice every time I speak with someone new.
I started by learning the F.O.R.D. Method, which focuses on four key areas of conversation:
- Family: “Do you have any kids?” or “How’s your family doing?”
- Occupation: “What do you do?” or “How did you get into that?”
- Recreation: “Got any hobbies you enjoy?” or “What do you like to do when you’re not working?”
- Dreams: “If you could live anywhere, where would it be?” or “Ever think about doing something completely different?”
Today, I met Bill, a Newport Beach local who rides his beat-up beach cruiser along the shoreline bike path, sipping a morning beer and listening to a transistor radio. His drink of choice today was a tall can of Budweiser. He was already a bit drunk when he flagged me down. Despite the awkward start, I decided to engage and used the F.O.R.D. method to guide the conversation. I asked, “What do you like to do when you’re not working?”
That one question opened the door. Bill told me about his inability to work and how he’s functionally retired, living on Social Security. I shared my retirement status, and we swapped stories about our interactions with the Social Security Administration.
Things got strange when he made a few digs about my weight. Rather than shutting him down, I used it as a segue into a discussion about health and my weight loss journey. I asked him about his own health, which, based on his enthusiasm, seems to be a favorite topic among retirees.
After 15 minutes covering a wide range of subjects, I gracefully wrapped up the conversation. Bill isn’t the kind of person I’d normally hang out with, day drinkers tend to dull my focus, but I managed. I have a feeling I’ll see him again tomorrow, though I doubt he’ll remember me.
Later that day, while walking along the shoreline, I met Joe, a professional photographer taking surf shots with an impressive Sony setup. After our greeting, I again used the F.O.R.D. method. I asked, “Is photography a profession or a hobby?” It was the perfect opening.
Joe shared his career story, and the conversation flowed naturally. I then applied another ChatGPT-recommended technique called the Rule of Three for Follow-Ups, which helped me dig deeper. After three related questions, I pivoted to another topic, asking another three. The whole exchange was fulfilling. We even traded Instagram handles; Joe’s is @jklingphotos.
After each conversation, I jot down notes to review with Wally, my ChatGPT coach. Wally offered more tips, which I later practiced in a phone call with my sister and during a conversation with a friend. I can feel myself improving, although the process still feels unnatural. Time will tell.
One important insight: I need to stay present. Eye contact helps, but more crucial is focusing my mind on the moment, listening to the other person instead of jumping ahead to my next point. I’m learning to contribute only when asked or when it truly adds value. That restraint doesn’t come naturally to me, I tend to call a dumbass a dumbass. For instance, when Bill began catcalling women, I resisted my knee-jerk reaction and instead asked how he interacts with people.
On the other hand, I’ve noticed that letting my mind wander means I’m not truly listening. And if I’m not listening, I’m not helping the conversation move forward. It sounds simple. I’m 64, I probably should’ve learned this in high school. But I’m learning now.







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