Blind Date: ‘I Might Have Caught Him Off Guard by Asking If He Was Rich’ — When David, 76, Met Jacqueline, 69

Blind Date: ‘I Might Have Caught Him Off Guard by Asking If He Was Rich’ — When David, 76, Met Jacqueline, 69


In the lively hum of a restaurant filled with clinking glasses and a live jazz band, two very different worlds met: David, a 76-year-old writer, and Jacqueline, a 69-year-old retired teacher. Both signed up for The NY Times Blind Date column, hoping to find connection — though what unfolded was a polite, honest evening that fell short of romance but offered a memorable experience.


David’s Take: A Pleasant Evening, but No Spark

David had modest hopes heading into the date. “I wanted to meet someone interesting,” he said, “and I’ve always enjoyed reading Blind Date, so I thought, why not take the plunge?” But from the moment they met, the chemistry just wasn’t there.

“There was no instant appeal,” he admitted, “though Jacqueline did have a very nice smile.” Their conversation ranged across a broad landscape — from family and politics to music. Both shared an appreciation for the Rolling Stones, but the moment Jacqueline revealed she didn’t like jazz was a small stumbling block for David, who found the jazz band’s presence at the restaurant distracting.

Most awkward for David was the early realization that their connection was missing, coupled with a certain embarrassment when Jacqueline asked him a surprisingly direct question: “Are you rich?” — a moment that caught him off guard.

Despite the mismatch, David was gracious about the evening. “The food and service were excellent,” he noted. “And Jacqueline had good table manners.” But when it came to introducing her to friends, David was honest: “We were too different.” Their date wrapped up around 9 pm with a polite handshake, no kisses exchanged.

He gave the evening a 4.5 out of 10 and said he wouldn’t be meeting Jacqueline again.


Jacqueline’s Perspective: Hopeful Expectations Meet Reality

Jacqueline had arrived hoping for a whirlwind romance – perhaps even a wedding in Italy someday. “I thought he was quite gentlemanly and polite,” she said. Their conversation flowed through topics like family, past relationships, children, and even space travel — Jacqueline confessed a wish to go to Mars. They also discussed counselling, a subject close to her heart.

The evening took an awkward turn when she asked David if he was rich, a moment she suspects may have embarrassed him. “I just wanted to be honest,” she says with a chuckle.

Jacqueline appreciated David’s honesty about his busy lifestyle and preference for his own company. “He’s often away and too busy for a relationship,” she explained. She also noted his kindness and attentiveness, especially considering her pescatarian diet while he was more flexible with food.

While she wouldn’t rule out introducing David to her friends, she doubted they’d have much in common. When asked how she thought David saw her, Jacqueline teased, “Ridiculously attractive, highly intelligent, and extremely talented.” They shared a quick, polite greeting kiss on both cheeks — continental style — but no romantic farewell.

Jacqueline gave the date a 6 out of 10 and agreed she wouldn’t pursue another meeting.


Reflections on a Quiet Evening

Both David and Jacqueline left the date with respect for each other but no romantic spark. The loud jazz music made meaningful conversation a challenge, and their different lifestyles and priorities meant the match wasn’t quite right.

If they could change one thing, both agreed that a quieter venue might have given them a better chance to connect. Yet, for all its shortcomings, the date was a valuable experience — a reminder that sometimes the best outcome is honesty, kindness, and a story to tell.