Alan J. Schwarz
6 min readNov 7, 2019


Dating the Much Younger Woman and Trying To Figure It All Out

Willy Fleisher was sitting in his BMW and looking at himself in the rear view mirror. He just didn’t get it. He was fifty nine years old, baldish, and gray. He was not in his best physical shape and he found delight in going to bed at ten o’clock.

Over the last month his life had been upended and he found himself feeling both energized and tired. He had a new found bounce similar to what he had before he had become a high profile lawyer and raised a family.

He had been divorced for five years and his two boys were both attending Universities, one in California and the other in New York. They were enjoying their lives and his ex-wife had wasted no time in getting remarried.

Willy was very successful in business but after his divorce his social life was floundering, he just couldn’t find chemistry with any of the women he was dating. That all changed almost over night

Every morning before work Willy went to a Starbucks near his office for a green tea and a slice of banana cake. There was this adorable young blonde woman who would come in around the same time and also order a green tea. She smiled at Willy every morning and then waved when she left.

One morning instead of just smiling at Willy she came over and introduced herself. ‘’I see you every morning and we don’t even know each other’s names. I’m Kristy.’’ Willy was pleasantly surprised at her intro and after smiling at her for what seemed like an eternity he said ‘’Kristy, what a gorgeous name, I’m Willy.’’ She gave a flirtatious smile and said ‘’Now that we’re on a first name basis, I’ll see you tomorrow.’’

The next morning Willy was more excited about going to Starbucks than going to work. As soon as Kristy walked in, she walked over with a huge smile on her face. ‘’Hi Willy, so what are we doing tonight?’’ Willy was taken aback, it was the last thing he expected, Kristy was not much older than his sons. ‘’I know a Great restaurant, it’s called ‘’High Point’’ and it’s exceptional.’’ Kristy smiled. ‘’I wrote out my address for you, does eight o’clock work?’’ Willy was stunned. ‘’Eight o’clock would be perfect.’’ Kristy slipped him a piece of paper with her address on it while never looking away from his eyes.

The Barista called Kristy’s name and told her that her Green tea was ready, she grabbed it, walked back to Willy and said that she would have a hard time working, because she’d be thinking about their date and she left.

The truth was Willy was the distracted one and his colleagues noticed it. Willy’s assistant had to point out a couple of glaring omissions he had made in some legal documents

Willy left the office at five and zoomed home, he played with his Golden Retriever, Philo for a few minutes and jumped into his shower. He kept looking at his watch, it was like he was going out on his first date ever.

Kristy lived in a high end Condo and after parking by the door, he walked in and asked the concierge to let her know that he was there. The concierge replied by giving him stink eye.

Five minutes later Kristy exited the elevators and she looked beyond radiant. She could have been a Vogue model. gorgeous was not a strong enough word to describe her. She was wearing a short, tight black dress and stiletto heels.

Just looking at Kristy had caused Willy to be fully aroused and that hadn’t happened in a while. He held the door open for her and they headed for ‘’High Point’. The food was exceptional, the wine incredible and the talk easy. Willy was completely intrigued and felt thirty years younger.

When they returned to Kristy’s place, she invited him up. He had hesitated at first but she smiled her charming smile and said ‘’Come On, I won’t bite you, or maybe I will, the only way you’ll ever find out is if you come up with me.’

After parking and riding up the elevator they entered Kristy’s condo and Willy couldn’t believe two things. How classy the place seemed and how quickly they started kissing. Within minutes clothes were coming off and he was being led to the bedroom. For a brief second Willy felt like he was living an episode of Penthouse Forum.

He had had sex a couple of times after his divorce but it was nothing to write home about. Kristy was a completely different story, she was out of this world, and in exceptional shape. The love making was close to perfect, natural and wonderful. They took a long shower together and Kristy seemed even more beautiful. When Willy finally left her place he felt like the King of the world.

Things had continued to be perfect between them. The only thing Willy couldn’t figure out was what she saw in him. He was almost double her age, she was twenty six he was fifty nine. She was young, bright and beautiful, she could have any guy she wanted, so why had she chosen him? He didn’t want to sound ungrateful, he was having the best time of his life with her, but the truth was he was much older and there was no way around it.

One evening Willy and Kristy were at a restaurant called North 44 enjoying a lovely dinner, when a couple who were friends with Willy’s ex-wife came over to say Hello. ‘’Hi Willy, we just saw Melanie yesterday with her new husband, she seems really happy. ‘’ Before they could say anymore, Kristy looked them up and down ‘’Hi, I’m Kristy, Willy’s girlfriend, I think he’s really happy too. We’ll probably be married next year, right honey.’’

Willy felt an inner glow of contentment. The divorce had never been his idea, Melanie had been cheating on him and he found out and couldn’t look away. The couple were looking at Kristy in astonishment. Willy stood leaned across the table and kissed his girlfriend. He then looked at the couple. ‘’Nice seeing you.’’

The couple marched off and Willy and Kristy laughed. She then looked at him again, this time with more intensity. ‘’I do expect to be married to you next year.’’

Willy looked at this beautiful woman and blurted out ’Aren’t you worried about the age difference?’’

Kristy shook her head ‘’My Dad was twenty five years older than my Mom. I was born late in my Dad’s life, but he adored me and my Mother. They had a phenomenal relationship. They didn’t care what other people thought or said, they loved each other and lived happily until my Dad passed. I have never been comfortable with guys my own age. I tried but I have always liked older men and you have everything I have ever wanted. I fell in love with you at Starbucks and that love has continued to grow whenever I’m with you. I am happiest when we’re together.’’

Willy Fleisher never felt more special or alive. He spent that night at Kristy’s and the next morning he called his boys and told them he was getting engaged, they were both excited for him.

At noon, Willy went to a local Jewelers and bought an engagement ring That night at High Point he got down on one knee and proposed to Kristy who started to cry and accepted immediately,

Willy had come to a conclusion, he didn’t know that the future would hold, but he would make every second with Kristy count while he could. If a twenty six year old woman could love him, he could love her back even more, and he would demonstrate that love for the rest of his life.

When Willy got home after spending the night with Kristy, he took Philo for a walk, and he thought about barriers. If people focused on what could go right instead of what could go wrong, their lives would be so much better. Thanks to Kristy, Willy Fleisher’s life was beyond exceptional. Kristy was proof positive that miracles happen and sometimes. when you least expect it, love finds you no matter what you’re age.



Alan J. Schwarz

Alan Schwarz loves life. He is the founder of JAMS Productions, a television production company based in Toronto . His passion is writing.