Diane agrees to a third date with Jack, even after he messed up the second one so miserably. Will this 50+ dating app relationship go anywhere? Read on.

To catch up on the first two stories about Jack and Diane, check out the first, Death by Millstone, and the second, The Second Date. I am writing these stories one at a time, with no idea or plan where it will go. The two characters interest me more than I expected them to. Who knows? We’ll find out together.

And now, enjoy their third date, a day trip to Santa Barbara.

A Third Date

Bob Gillen

Jack Marin backed his white Ford F-150 effortlessly into the parking spot half a block from Stearns Wharf in Santa Barbara.

“We’re here,” he whispered to Diane Somers sleeping in the passenger seat. Diane opened her eyes. She took in Jack’s face, turned to see the beach across from the sidewalk.

“That was fast,” she croaked. “Oh, I was really out, huh?”

“Since we got on the 101.”

“Wow. Hardly sleeping for two nights makes a girl sleepy.”

“Take your time waking up,” Jack said. He pressed the slider to open Diane’s window. The cool ocean breeze drifted in.

“Oh that smells good.”

“Never disappoints.”

Diane straightened up, pulled down the visor mirror. “I need a bit of makeup.”

“If you say so. Looks good from where I sit.”

She freshened her lipstick, ran hands through her hair.

“How’d you score a spot so close to the wharf?”

“I lived in New York City for five years. Finding a parking spot is a learned skill.”

“I didn’t know you lived there.”

“Long time ago, after graduation. Before I came back out to LA.”

Jack closed the window. “Let’s head out on the wharf.”

The two walked along the wharf as cars passed back and forth next to them.

“I have to say, Jack, I really hesitated when you called and asked me to come here.”

“Yeah, I really messed up our last date… I’m a shitty listener.”

Credit: CheshireCat.com

“More than that.”


“I was flattered you called. But after our second date didn’t go well, I did not want to be miles from home, depending on you to drive me back if it went south again.”

Jack stopped, stepped aside to the railing. “I know I really messed up both dates, but I wanted to see you again so badly. I thought some ocean air and a good dinner would help.”

Diane smiled. “I missed you too. I am still concerned that this won’t work out, but I’m game to try again.”

The passing cars caused the wooden beams of the wharf to clatter as they drove over them. Jack smiled. “Have I told you I’ve done and said some incredibly stupid things in my lifetime. Almost always around a girl.”

“Why am I not surprised?”

Jack pointed to the passing cars. “All the clattering of the wharf reminds me…when I was in the eighth grade, I had a girlfriend.”

“Wow, this is ancient history.”

 “Cute.” Jack smiled. “Her name was Patti. One chilly spring day we rode our bikes to the park at the end of our town. A wooden car bridge crossed a large creek near the park. Patti and I, and another couple we were tight with, we climbed up under the bridge, right under where the cars drove across. We heard all of that clattering of the wooden beams. Anyway, we were kissing. It was a nice moment. Secluded under there. The other couple kept on kissing. I kissed Patti for a bit, then said, “Okay, I’m done. We can go now.”

“You didn’t?”

Jack extended his palms in surrender. “I was an idiot. Alone with my girlfriend. And I cut it short. So stupid!”

“Yeah, Jack. That was stupid.”

Seagulls screeched alongside the wharf. Jack shrugged. “Let’s get some ice cream.”

They walked to the end of the wharf. Jack got a vanilla cone, Diane Rocky Road in a cup.

“My friends tease me. Call me plain vanilla. I love the flavor, and I hate bits of stuff in my ice cream.”

Diane waved her index finger. “I won’t offer you a taste of mine.”

They found an empty bench facing out at the harbor. 

“Do you feel rested after sleeping in the car?”

“I do. Thanks. I hope it wasn’t rude of me, but I was so tired.”

“Trouble sleeping?”

“I think aliens have invaded my cat’s brain. He now paces around the house all night.”

“That’s weird.”

“I adopted him two years ago. Hoping for company around the house. They told me his name was Pepper. After a week I started calling him Zero. Still do.”

“Odd name.”

“He sleeps all day. Wakes up to eat and pee. Does not meow or purr. Will not snuggle or let me pet him. So I call him Zero…as in, I give zero fucks about this cat.”

Jack almost dropped his cone. “That’s harsh.”

“After the last two nights, I mean it even more. He’s insane.”

“So, not only is he not good company, he now keeps you awake at night.”

Diane nodded, finished her Rocky Road. She stood to find a trash can. “Let’s walk a bit. I need to stretch my legs.”

They walked back along the wharf to the street, turned towards the harbor where hundreds of boats were docked. Both enjoyed the sea air. Neither felt the need to talk. 

When they reached the end of the sidewalk, Diane said, “I’m hungry. Got any ideas for restaurants?”

“As a matter of fact, I do. There’s a great Italian place up State Street. We can walk there, or get the truck and drive up.”

“I don’t mind walking.”

“Okay, let’s go.”

They walked back along the beach, headed up State Street. The street was still closed to auto traffic, since the beginning of the COVID lockdowns. Bicycles whizzed past, tourists and residents wandered the street. Jack moved to hold Diane’s hand, but a surge of tourists forced them to walk single file. When they reached the restaurant. Jack and Diane got seated in a quiet outdoor section.

Santa Barbara City freshly painted bike lane on State St. and Figueroa St. RAFAEL MALDONADO/NEWS-PRESS

“So, I promised myself I would not dominate the conversation. Tell me something about your last job, Diane. The one you retired from.”

The server brought a plate with a baguette and olive oil with pepper. Diane wolfed down a piece. 

“God, I was hungry.”

Jack placed his napkin on his lap. “This is nice. I can’t remember when I last ate someplace that had cloth napkins.”

Diane laughed. “I hear you.”

“So, tell me about your job…”

Diane said, “I had no plans to retire then, but I couldn’t take the company anymore.”

“They forced you out?”

“In a way. I was in tech sales support, covering retail clients on the west coast. We had some management changes, they reorganized the company structure. Some bright light decided that all sales and sales support people should be based out of Indianapolis. They wanted all of us to relocate.”

“Relocate from LA to Indianapolis?”


The server stepped up. “Any questions about our menu?”

“I think we’re ready to order. Diane?”

“I’ll have the salmon piccata.”

“Excellent choice. And you, sir?”

“Chicken parmesan.”

The server took their menus and walked away.

“I see why your friends tease you.”

“What do you mean?” Jack asked.

“Chicken parm. Doesn’t get any more vanilla than that.”

Jack raised his palms in protest. “I go for what I like.”

Diane smiled. “Whatever.”

“So, back to you. Relo to Indianapolis.”

“Most of our customers were based in the east. The company figured they might as well put all of us nearer to them.”

“With more travel for you, for the west coast.”

“Yeah, plus summer humidity, winter snow and ice, and further away from my daughter.”

“Last time you mentioned you and she were estranged.”

“A topic for another time,” she said.

“Okay. Do you have grandkids?”

“None yet.”

“Yeah, me too…okay, so you quit and took early retirement.”

“Not exactly. I stalled. Finally, they offered me a severance package, and I jumped at it.”

Jack dipped a piece of bread into the olive oil and pepper. “Do you miss the work?”

“I miss the travel. Discovering new cities. Every trip staying in a good hotel. Great restaurants. Spa at night. Most of it on the company dime…and I miss fixing issues for my customers. The best feeling…”

“Yeah, I get that.”

Diane laughed. “One of the best fixes…I would show up at a retail location. Their point of sale equipment was acting erratically. I’d spot right away that they had tied the electrical cables alongside the data cables. Electrical interfered with the data transmission. I would fuss over it for a while, simply separate the cables, and voila, problem fixed. The customers loved me.”

“And here you are, cruising, no worries.”

“Eating a lovely Italian dinner with a man I hardly know yet. Who knew?”

After dinner and coffee, Jack and Diane walked back down State Street to Jack’s truck. 

“Would you be interested in adopting a cat?” Diane asked.

“No way. Animals are okay, but I am not a pet person.”

“I may have to give him up. I can’t live like this. I need my sleep.”

Jack nodded.

“And please, Jack. No suggestions about me spending a night at your place.”

“It never entered my mind.”

Diane turned to him. “Am I not attractive enough?”

Jack laughed. “Between a rock and a hard place… yes, you are attractive. And yes, I am a slow mover. Very slow.”

“Sounds fair,” Diane said. “Just kidding you. I will give up Zero, and then we can take it as it comes.”


Jack reached over, took Diane’s hand, and kissed it gently. She blinked, smiled.

Jack drove his truck onto the 101 South. He turned on one of his playlists. Art Tatum on the Pablo Group Masterpieces albums. He chose the session with Ben Webster on sax. “Chill. If you need to, take another nap. I’m cool with that.”

“I had coffee, but I may just do that. Walking and ocean air did me in.”

‘Call you when we get to your place.”

Jack smiled, steered south. Said to himself, Look at me, spending a day with Diane and not fucking it up. Go, me.