Dean saw his ex-wife, Gian, in the front row, a young man beside her, his hand resting on her shoulder. Dean in the middle of a romantic love song, and his voice trembled for just a moment. Wait, cuz how Dean finished that song and what he did for Gian didn’t just show how professional he was, it showed everyone how deeply he still loved her.
The second time around wasn’t supposed to hurt. Dean had sung it a hundred times. maybe more in rooms just like this one. Dark corners lit by table candles. Cigarette smoke drifting under amber spots. The orchestra tight and smooth behind him. It was a good song, safe, the kind that let him coast through the middle of a set while people finished their drinks and leaned back into their chairs.
He’d been doing this for so long that his body knew the notes before his brain did. muscle memory carrying him through verses while his mind drifted to tomorrow’s tea time or whether the Dodgers would cover the spread. The Sands showroom was packed tonight. Every table sold out, standing room only at the bar.
Tuesday night in March, nothing special on the calendar, but word had gotten around that Dean was in top form lately, and people wanted to see it. The kind of crowd that tipped well and laughed at the right moments and made his job easy. 400 people, give or take, all dressed up and ready to be entertained. He’d opened with Ain’t That a Kick in the Head.
Got them loose and happy. Then slid into Memories Are Made of This while they were still warm. Standard stuff. He was barely thinking about it. Just letting the routine carry him forward the way it had a thousand times before. Between songs, he’d done his bit about the drunk act, pretended to take a sip from the glass on the piano that everyone assumed was whiskey, but was actually apple juice.
Got the laughs he was supposed to get. Then he’d called for the second time around, and Eddie had counted it in, and Dean had started singing about love and second chances like he actually believed in them. But tonight, the song landed different. He was halfway through the second verse, his eyes doing what they always did, sweeping the room in that slow, easy way that made every table feel like he was singing just for them.
Front row, middle section, back corner, repeat. A smile here, a wink there. Selling the fantasy that Dean Martin knew you personally and thought you were swell. It was the job. He was good at it. Then his eyes hit the front row, table seven, and everything stopped. Not his voice.
His voice kept going because his voice was a professional and didn’t wait for his heart to catch up. But everything else, the easy rhythm, the automatic charm, the distance he kept between himself and the words he was singing. All of it collapsed in the half second. It took his brain to register what his eyes were seeing. Shian, his Jian, except she wasn’t his anymore, hadn’t been for 3 years.
But his chest didn’t seem to have gotten the memo because it locked up tight the moment he saw her face in the candle light. She looked exactly the same. Same dark hair swept back off her shoulders. Same way of holding her chin when she was listening to music. Same small smile that meant she was enjoying herself but didn’t want to make a show of it.
She was wearing something green. Emerald maybe or hunter green. He couldn’t process the details through the sudden tunnel vision. And she looked happy. That was the part that hurt most. Not angry happy or proving something happy, just happy, relaxed. The kind of ease she used to have with him back in the early days before everything got complicated.
Before the touring schedule became a wall between them. Before the late nights and the drinking jokes that weren’t always jokes. Before the long silences over breakfast became the whole marriage instead of just the rough patches they promised each other they’d work through. He remembered their first anniversary.
They’d been broke, barely scraping by on his club dates, and he bought her a single rose with money he should have spent on gas. She’d cried, told him he was an idiot, kissed him anyway. That was Gian. Practical and romantic in equal measure. The kind of woman who could balance a checkbook and still believe in grand gestures. She’d believed in him when nobody else did.
When the comedy duo with Jerry was falling apart and everyone said Dean would disappear without the funny man to prop him up, Gian had looked him in the eye and said, “You’re going to be bigger than all of them. You just have to trust yourself. He trusted her more than he trusted himself back then.
Maybe that was part of the problem. And next to her now, his hand resting on her shoulder like it belonged there, was someone Dean had never seen before. Young, maybe 30, 32, good suit, good haircut, the kind of cleancut look that said steady job and reasonable bedtime. And probably didn’t forget anniversaries.
The kind of man who came home for dinner. The kind Gian deserved. The kind Dean had never quite managed to be. His voice hit the bridge and he realized with a sick drop in his stomach that he was singing about second chances, about finding love again after you’d lost it the first time. And his ex-wife was sitting 10 ft away with her hand in another man’s.
And Dean was the cautionary tale the song was warning people about. The orchestra kept playing. They didn’t know. How could they? From where they sat, Dean looked the same as always. Smooth, unflapable. The guy who could charm his way through anything. They couldn’t see that his hands were shaking just slightly. Or that he’d stopped breathing through his nose because if he did, he might actually lose it completely.
Notice something here because it matters for what comes next. Dean had a rule about performing, one he’d never broken in 25 years of doing this. The audience doesn’t pay to see your problems. They pay to escape theirs. You leave your mess backstage. You walk out under the lights and you give them the version of you they came for.
Didn’t matter if you were hung over, heartsick, or halfway to broke. You did the job. But this wasn’t a problem. This was Gian. A woman three tables back later told her husband she saw the exact moment Dean’s face changed. It was like watching someone get punched, she said. But he kept singing like nothing happened. That’s not quite right.
Dean didn’t keep singing like nothing happened. He kept singing because something was happening. Something bigger than the song or the room or his pride. And he needed to figure out what the hell to do about it before he got to the final chorus. His mind was racing. Did she know he was performing here tonight? Had she come deliberately, or was this one of those cosmic jokes where the universe decides to kick you in the teeth just to keep things interesting? Was she trying to send him a message? Or was the message that there was no message that she’d
moved on so completely that sitting front row at her ex-husband’s show didn’t even register as awkward? The Sands was her favorite room back when they were together. She used to sit at this exact table or close to it, nursing a Tom Collins and watching him work. After the show, she’d wait in the dressing room and they’d walk back to the hotel suite together.
Her arm linked through his dissecting the performance. You rushed that second verse, she’d say. Or the bit with the hat worked better tonight. She heard things nobody else did. She knew him better than he knew himself. Maybe that’s why she’d left. The young man leaned over and whispered something in her ear. She smiled, squeezed his hand.
Dean watched it happen and felt something crack in his chest that he’d thought was already broken. The gesture was familiar. Dean used to do that during shows. Lean over midong, whisper some stupid joke in Jane’s ear just to make her laugh while he was supposed to be working. She’d swat at him and tell him to focus, but she’d be smiling. It was their thing.
Now it was their thing. This young guy and Gian, some new version of intimacy that didn’t include Dean at all. The third verse was coming. 30 seconds, maybe less. He had to decide. He could play it straight. Finish the song like she was just another face in the crowd. Take his applause.
move on to something upbeat and brainless that would let him coast to the end of the set. That was the smart move, the professional move. But then Gian looked up and their eyes met and Dean saw something flicker across her face. Surprise maybe, or recognition that he’d seen her, and whatever wall he’d been building in his chest fell apart completely.
Stop for a second because you need to understand what was at stake here. Dean Martin’s whole career was built on one thing. Making it look easy. The drinking, the girls, the charm. It was all part of the bit. The lovable Lush who stumbled through life and somehow always landed on his feet. People loved him because he didn’t take anything too seriously, including himself.
He was fun, uncomplicated, the guy you wanted at your party because he wouldn’t make things heavy. But Go had seen the other side. The side that woke up at 3:00 a.m. worried about money. The side that beat himself up for missing his kids’ school plays. The side that sometimes drank because it was the only way to shut off the noise in his head about not being good enough, smart enough, present enough.
She’d loved him anyway for a while. And then she couldn’t anymore. Dean had spent 3 years rebuilding the wall between who he was and who he pretended to be. Three years making sure nobody saw the cracks. Three years perfecting the illusion that everything was fine, that the divorce was mutual and amicable, and he was doing great. Really great, never better.

And now she was sitting in front of him with someone else’s hand on her shoulder. And Dean had about 20 seconds to decide whether to keep lying or tell the truth. He chose the truth, not with words. He couldn’t change the words. The song was the song, but with everything else, he let his voice crack on the word love. Not a lot, just enough that people would notice something was different.
He let his eyes stay on her, not in a creepy way, but in a way that said, “I see you and I remember everything and I’m sorry.” The orchestra noticed. The piano player, Eddie, gave him a look that said, “You okay?” Dean gave the tiniest nod that meant, “Keep going.” and Eddie did, but softer now, pulling the arrangement down to give Dean room to breathe.
Listen to what happened next, because this is where it gets complicated. Dean didn’t sing to the room anymore. He sang to Gian every word, every note. He aimed straight at table 7 like he was 22 again. And they were back in that little club in Cleveland where he’d first worked up the nerve to ask her to dinner. He sang it like an apology, like a confession, like a goodbye.
And Jane, God love her, didn’t look away. The young man noticed. Dean saw it happen. The guy’s posture stiffened, his hand tightened on Jane’s shoulder, his eyes cutting between her and the stage, trying to figure out what was going on. But Jane didn’t move. She just sat there, her eyes locked on Dean’s.
And for the length of one song, they were the only two people in the room. A waiter near the back later told the night manager he saw three women crying by the time Dean hit the final verse. I don’t even think they knew why. He said they just knew something real was happening up there. Dean reached the last chorus, the part about getting another chance at love, about being smarter this time, and he changed the emphasis where he usually hit chance hard.
Making it optimistic, he softened it. Made it a question instead of an answer. Made it sound like he was asking her, “Do you think we could have if we’d known then what we know now?” Her eyes welled up. Dean saw it, and something in him both broke and healed at the same time. He finished the song. The last note hung in the air for a beat longer than it should have.
And then the room erupted. Applause, whistles, some people standing. They didn’t know why it was different, but they knew it was. They just witnessed something rare. A performer forgetting to perform and just being human instead. Dean took his bow, his eyes still on Gian. She was clapping, tears running down her face. The young man’s arm around her shoulders now protective. Dean understood.
The guy wasn’t a threat. He was what Jian needed. stability, presence, someone who showed up. Dean couldn’t begrudge her that, but he could give her one more thing. He walked to the edge of the stage, which he never did during a song break, and reached into his pocket. He pulled out his pocket square, white silk, monogrammed with his initials in navy thread, the one Gian had given him on their fth anniversary, with a card that said, “So, you’ll always have something classy on you.
” He still carried it every show, every single one. It was stupid and sentimental, and he’d never told anyone, had waved off the questions when people asked why he never actually used it as a pocket square, but now seemed like the time to let it go. He looked at her and she knew. Her hand went to her mouth.
The young man beside her stiffened, confused. Not understanding what this small piece of silk meant or why the woman next to him had suddenly started crying harder. Dean looked at Gianne and then at the young man and made a decision that surprised even himself. He folded the pocket square carefully, walked to the very edge of the stage where the lights were hot enough to make him squint and handed it to the young man.
Not to Gian, to him. The room went quiet, trying to understand what they were witnessing. A few people in the back stood up to see better. Eddie’s hands hung frozen over the piano keys, waiting. Dean leaned down close enough that only their table could hear, his voice barely above a whisper, but clear as crystal.
She likes her coffee with cream and two sugars. She pretends she doesn’t care about birthdays, but she does. And if she ever tells you she’s fine when she’s clearly not, don’t let it go. Ask again. Keep asking until she tells you the truth, because she will eventually if she trusts you enough. The young man’s eyes widened.
His throat worked, trying to process what was happening. He looked at Gian, who had tears streaming down her face now, not bothering to hide them anymore, her whole body shaking with the effort of keeping quiet. Then slowly, reverently, he took the pocket square from Dean’s outstretched hand. “Take care of her,” Dean said, and his voice cracked on the last word, the mask slipping completely for just a second.
“She deserves someone who can do what I couldn’t.” Dean straightened up, gave Gian one last look, a look that said, “I loved you, and I still do, and I’m glad you’re happy.” and walked back to center stage. The orchestra started the next song. Something upbeat, something safe. Dean sang it perfectly.
The mask back in place, the consumate professional. But everyone in that room knew they’d just seen something else. Something true. The young man at table seven tucked the pocket square into his jacket. Gian reached for his hand. They stayed for the rest of the set. Years later, after Dean died, a man called one of those late night radio shows that took stories about celebrities.
He said he’d been at a Dean Martin show in Vegas in ‘ 67, sitting front row with his girlfriend. Said Dean had handed him a pocket square with something written on the inside, “Take care of her. She deserves it.” He said they got married 6 months later and that square was in his pocket on their wedding day.
He said his wife kept it in a drawer by her bed until she died. And sometimes he’d catch her holding it, crying quietly. He said he never asked why, because he already knew the night of the performance. After the set ended and the crowd filed out, Dean went back to his dressing room and sat in the dark for an hour.
Didn’t turn on the lights, didn’t pour a drink, though the bottle was right there on the counter where it always was. just sat there with his hands folded in his lap, feeling the full weight of what he’d just done. The rest of the set had been torture. He’d powered through six more songs, all of them feeling hollow and mechanical compared to what had just happened.
The crowd ate it up. They didn’t know the difference. Couldn’t tell that Dean’s mind was somewhere else entirely, but he knew every note felt like lying. between songs while Eddie played fills and the audience chattered. Dean had snuck glances at table 7. The young man had his arm around Jian’s shoulders.
Now, no longer just resting, but actually holding her protective Dean understood the message. The guy wasn’t stupid. He’d felt the current running through that song, seen the way Jon’s eyes had locked on Dean’s, and he was marking his territory. Fair enough. Dean would have done the same thing. But Gian hadn’t looked away.
Not during the next song or the one after that. She kept her eyes on the stage on Dean. And there was something in her expression that he couldn’t quite read. Sadness maybe or recognition or both. A waitress named Carol, who’d been working the floor that night, told her roommate something strange had happened during the show. I’ve seen Dean Martin perform 50 times, she said, and I’ve never seen him look at anyone the way he looked at that woman in green.
It was like everyone else in the room disappeared. Her roommate asked if maybe they were having an affair. No, Carol said it was worse than that. It was like watching someone say goodbye to something they should have held on to. Eddie, the piano player found him there around midnight. “You okay?” Eddie asked.
Dean didn’t answer right away. Then you ever love someone so much that you want them to be happy even if it’s killing you? Eddie nodded. Every day of my life, pal. Dean smiled at that. Not his stage smile. The real one. The song went okay. Eddie offered. Yeah. Dean said. It went okay. That was the last time Dean sang the second time around in public.
He pulled it from his set list the next week. replaced it with something jaunty about cocktails and moonlight. And nobody asked why, but the musicians knew. The ones who’d been there that night, who’d seen what happened when Dean stopped pretending and just let himself feel it, they knew. And sometimes late in a set when the crowd was drunk and happy and Dean had that look on his face that said he was somewhere else entirely, Eddie would play the opening chords.
Just the first two bars quiet under whatever Dean was singing. A reminder, a memorial. Dean never acknowledged it, but he heard it every time. If you enjoyed spending this time here, I’d be grateful if you’d consider subscribing. A simple like also helps more than you’d think. Janna remarried the young man from table 7. They had 43 years together.
Dean never remarried, though he dated. The pocket square story eventually got back to him through a mutual friend. And when it did, he just nodded and changed the subject. But on quiet nights when the shows were done and the crowds were gone, Dean would sit in his dressing room and hum the tune the second time around softly to himself, not like a performer, like a man who’d loved someone and let them go and somehow found a way to be okay with it.
If you want to hear about the night Frank Sinatra found Dean in that dressing room and what Frank said that made Dean laugh for the first time in weeks, tell me in the comments.