It's A Date DUMBO

It's a Date!

Compiled by Dale Kaplan
Edited by Gisella Snailer
Mural by Tara Dixon

Dates can be good, bad, strange, fabulous, perfect or terrible, but at least they make great stories. When I was young, I would call at least 5 girlfriends after a date to report on every single detail. Those were days when people actually spoke on the phone, and there was no shortage of tales to tell.

When I decided to ask Dumboites to report on their best, worst, or most memorable dating scenarios, I also looked back on my own life for inspiration. Thanks to all our members who have generously shared their stories for a fun and entertaining Valentine’s Day.

Kenny Solomon - The bane of Ben Affleck's existence

Kenny Solomon – Artist

When I was in high school I dated a girl named Cheyanne. We broke up and then we got back together. Before we got together she was dating a guy named Ben. He was a Cambridge kid and I was a Brookline kid. When we broke up, she got back together with Ben. On again off again like ping pong. I heard about Ben a lot but we never met except for one time when we were all in limbo. One day I went to pick up Cheyanne at a bakery where she worked, and while I was waiting for her, Ben walked in. We stood on opposite sides of the store staring at each other.

Cheyanne was a year younger than me. We tried to stay together while I went to college and she was still in high school, but it did not work. We remained friends and she got back together with Ben. They stayed together for years. About six years later she told me that Ben had found some success as an actor and was writing a film with his friend Matt about a blue collar kid who worked as a custodian at Harvard.

Meanwhile one of my best friends found a job at Miramax working as Harvey Weinstein’s assistant. Unexpectedly he told me that he had to fly to L.A. on a private jet with another assistant and Matt Damon. When he landed he called me to say that he had a great story to tell me. “It’s the four of us on a plane. At first I was intimidated by Matt. But then I realized that we are sort of peers. So I went over to him and said hey, you and I are three degrees of separation. Matt says “Oh yeah, how?” He tells Matt that one of his best friends dated Ben’s ex girlfriend. Matt says Cheyanne? And Mark says yes, Cheyanne and his name is Kenny Solomon. “Oh my god,” exclaimed Matt, “he was the bane of Ben Affleck’s existence for years.”

Ruby Andreolli
Ruby Andreolli

Ruby Andreolli – Egg Baby


My mother was desperate to get me married. She said she knew someone who knew someone who knew someone, but she made it sound very legit. The guy called me and we planned on meeting for an early evening coffee.

Before I went on the date, I asked a friend to be my security guard and hang out at the bar next door just in case I had to make a quick get away.

When I arrived at the cafe, I saw a guy in the window who looked like a complete mess, and I said to myself, “there is no way that this is my date.” I called the number of the person I was supposed to meet to see if he was already inside. When I dialed the number, I saw the fellow in the window answer the phone. I almost plotzed, but I was a good sport and went inside. Hey, looks aren’t everything.

Before I even had a chance to sit down, he said, “I got here early and I’m almost done with my coffee, but you can go wait on the line and get yourself whatever you want and pay for it,” and he pointed at the cash register.

I told him, “I am really sorry, but this is not going to work.” He offered me a slight rebuttal, but I just decided to leave and meet my friend. Then, I got really upset with my mother. I called her and asked if she had anything against me and what she was thinking. She admitted she hardly knew the woman who had set this debacle up.

She never attempted to set me up again and I forgave her. After all, she is my mother.

Luke Masella in front of Tara Dixon's Love Spiral Mural

Luke Masella – Good Brother


I was going out on a date with a girl that I knew in high school. Before we were about to leave her house, her father was in the driveway and his car wouldn’t start. He asked me to go to the local repair shop and borrow some jumper cables. When I went in the store, introduced myself, and asked to borrow the cables for my date’s father, the man took me aside and said, “that guy has been trying to steal jumper cables from me for months!”

I was caught dead in my tracks and started to sweat. I just explained to her father that he had lent them to someone else. I will never forget that scenario.

Lindsay & Dino

Lindsay – Glam Expressway


My best date was back in the summer of 2008. Dino had just come back from an international tour with one of his artists that morning. I remember him picking me up and us going for lunch at an Italian Restaurant in the Meat Packing District. I remember sitting outside when Dino gave me a gift from his travels (I think it was a bracelet; I am sorry to say that I lost it). After we ate, he took me on a boat ride (just the two of us) and he showed me a list of all the reasons he liked me that he’d made on the plane.

Twelve years and three kids later, the list is still in an old phone that my daughter plays games on. The reason this was my “best date” was because of the effort made on Dino’s part. I could tell that he planned the date and it really showed his interest and love.

Santo and his Bride's big Day
Santo Today 🙂

Santo Fareri – SRF design

The best date I’ve ever been on took place about 42 years ago.

On its face, it was an unremarkable first date. We saw a movie: Saturday Night Fever. She lived in Bensonhurst, so seeing it was required. Then, went to a diner. What made it so memorable were 2 things that occurred at the end of the evening.

First, was the unshakeable feeling when saying goodnight that this would be the beginning of a very long story.

Then, after giving her a minute to get rid of her gum, there was that kiss goodnight. Our first kiss, not exactly chaste, but far from passionate, gave me chills. Looking at her as I pulled away, I wondered if the feeling was one-sided. She looked thoughtful, a bit shaken really, & said she wanted to try another kiss. With her eyes still closed after our second kiss, she described feeling an electricity, a tingling, putting to words what I couldn’t. That was the end of the date, but not the story.

We celebrated our 41st wedding anniversary last summer. 41 years filled with so much more good than bad; there was some sadness, but so very much happiness. 41 years worth of electrifying, tingling, chill-inducing dates!

Tanya then and now - Someone in the picture was the date she describes below...

Tanya Rynd – Superfine

I don’t usually date, for what it’s worth I dive right into relationships,

However, my best date ever took place when I was 20 years old on the back of a Harley with one of my long term sweethearts. We took a ride through the Jemez Mountains of New Mexico and our destination was the sacred hot springs where we hiked and skinny dipped. It was our first date.

I did not wear a helmet because there was no helmet law at that time. It was glorious.

That afternoon was a remarkable adventure just like the rest of our relationship.

Hint: One of the women in the photo above was my sweetheart. Guess who?

Half a slice... Really? Thank you to our friends at Front Street Pizza for the slice!

Dale Kaplan – Dumbo Direct

When I was attending Midwood High School in Brooklyn, I dated a guy named Glenn B. He was not physically attractive at all, but girls loved him. He was very charismatic. He came over on a Sunday with his friend’s car, rang my bell and said, “Dale, get your bathing suit. We are going to Manhattan Beach.” As I was running out the front door, my mother yelled after me, ”Dale, let me give you some money.” Glenn replied, “no worries, Mrs.Kaplan, I will take care of it. I have plenty of dough,” (his father was a doctor).

We get to the beach, and he never offered to buy me one thing. The Fudgy Wudgy man passed by like 100 times, as did the ice cream cart and the iconic Disco Freddie who sold ice cold cans of soda. I guess at that time I was too shy to say anything…

Well, when we finally packed up and crossed the walkway to Sheepshead Bay, Glenn said, “let’s go for pizza.” By this time, I was starving. When I approached the counter I ordered a slice and a coke. Glenn B. then interjected this infamous request: “make that a small, and can you cut the slice in half?” This was 47 years ago, and I can remember his words like it was yesterday. When I told my mother, she said, ”cheap goes all around. If he is cheap with money he is most likely cheap with love.” That was our last date.

Dale's Parents - Pearl & Ike Kaplan

I wasn’t actually on this date, but it did lead to my existence and it’s a good one.


My mother and father started dating in August of 1947. It was set up by my mother’s nephew who had just become engaged to my father’s sister.  My mother, Pearl, was 32 at the time, which was considered old for an unmarried woman, and my father, Ike, was 37 and had recently returned to Brooklyn after serving in WW II.  


They met in August and it was a good match. My mother was crazy about my father. She loved his beautiful blue eyes, dimples and dry sense of humor. The feeling was mutual.


On Christmas Eve, which also happened to be Chanukah, they went out to a movie. When they arrived at my mom and grandmother’s apartment, my mother presented my father with a beautiful shirt and tie for the holidays. She received nothing in return. When he left to go home, my mother was livid. She complained to my grandmother that he was thoughtless and came empty handed. “Not even a little something?” She was really upset.


About ten minutes later, the door bell rang and he asked if he could come up because he forgot something. She ran down the two flights to open the door on Carroll Street in Brooklyn and he there he was standing in the freezing cold. She did not even want him to come upstairs. My mom, asked, “OK what did you forget?” He put his hand in his coat pocket, took out a little velvet box with a diamond ring and said, “I forgot to ask you, will you marry me?” The rest is history. Pearl and Ike were happily married for 52 years.

Glam Expressway

Good Brother


Ken Solomon

SRF Design

  • Avatar
    February 16, 2020 at 1:35 am

    Great content! Super high-quality! Keep it up! 🙂

  • Avatar
    dale kaplan
    March 19, 2020 at 10:08 am

    Thank you.

  • Avatar
    Marybelle Loetz
    April 2, 2020 at 7:54 am

    This is very interesting, You’re a very skilled blogger. I’ve joined your feed and look forward to seeking more of your great post. Also, I’ve shared your site in my social networks!

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