Second Chance

By Dan Smith

Published on Aug 20, 2024

Gay

Second Chance Chapter 1 - Remembering the Past

Nostalgia was not one of my usual weaknesses. I tended to be a positive, forward-thinking person, focused more on future opportunities than dwelling on the past. But with my 65th birthday approaching, I had been reflecting a lot on my life lately.

65 seemed like such an arbitrary number to obsess over, since nothing was actually changing in my life. I was not planning to retire for at least a few more years. (I had stepped down as a managing partner at my law firm when I turned 60, but I still maintained a full case load). But 65 was one of those milestone birthdays (I suppose, since 65 USED o be the mandatory retirement age). As a result, it had me thinking about my past more than usual for the last couple of weeks.

Looking back, I felt like I had lived a fulfilling and mostly happy life. I'd gone to a good college then spent two years in the Peace Corps in Costa Rica before enrolling in law school. After finishing my law degree, I joined a good firm back home here in Chicago, focusing mostly on immigration law. I made partner by the age of 32, and by 45, I was a named partner in the firm that became Scheinberg, Ellis, and McAllen. (I was the Ellis in the firm's name.)

My personal life had been fulfilling as well. In college, I had dated a few girls but never had sex with any of them, which was perfectly fine with me. I eventually came to realize that I was gay while I was in the Peace Corps, though I was careful not to act on it while living abroad. I came out to my family just before starting grad school. My younger sister was great about it; we had always been close.

My older brother was indifferent, but then, we'd never been that close anyway. My parents struggled a little but never stopped loving me. It was the height of the AIDS crisis then, so mostly they were concerned about my staying healthy.

I entered law school determined to be out and proud. I joined the gay student alliance in school and dated a few guys, but nothing too serious. I had several short relationships once I started working, but the crazy schedule of a junior associate attorney left me with too little time to devote to my personal life, so most of the guys I dated got frustrated pretty quickly and broke up.

It was when I'd been with my firm for about five years that I met Pablo. He was a case worker at a local center for immigrants. Originally from Central Mexico, he'd come to the United States with his family during high school. After he finished college, he worked as a corporate banker for almost a decade. He made fantastic money in banking, but he found the job unfulfilling. So he went back to school to get a degree in social work, and now he provided services to immigrant families. His center regularly brought me in to work with their families seeking a green card or citizenship or trying to avoid deportation, and I worked with Pablo on a couple of cases. I had noticed how handsome he was, with curly black hair, light caramel-colored skin, and strong, muscular arms, but I had no indication that he was gay, until one day as we were wrapping up some paperwork on a client, he asked me if I would be interested in going out for a drink.

"Sure?" I said, tentatively, not certain what his invitation implied. "Where?" I asked.

"Christopher Street?" he suggested, naming one of Chicago's best-known gay bars.

"Oh!" I said. "So, like a date?"

"Just drinks," he responded.

"Oh," I said, obviously a little disappointed.

"I mean," he continued, "it could be a date if you wanted."

"Drinks is fine," I said.

But it ended up being very clearly a date, the first of many. We met up that Friday night at Christopher Street and ended up talking for a couple hours about our lives. We immediately clicked. I was taken by his huge heart and his passion for helping others. He must have seen something in me as well, because the date was extended. Not wanting to go home yet, we walked a few blocks over to another gay dance club, Berlin, and danced there until closing time. I had taken the L in, and I was planning to grab a cab back to my apartment, which was some distance northwest, but Pablo suggested that I just come back to his place, which was only a couple of blocks away.

"It's too late for you to go all that way. Just come to my place. We can just sleep."

I would like to say that we took things slowly, and that we gradually fell in love with each other, but the truth is that we did not "just sleep" that night. As soon as we stepped into his apartment and closed the door, we were all over each other, making out with a passion that could have melted an iceberg. Our clothes were soon scattered across the living room, and we ended up on his bed, fucking for hours. He fucked me first, then I fucked him, then we snuggled for a while, then he fucked me again. We didn't get to sleep until the sun was starting to come up and the floor was littered with used condoms.

That was the beginning of an amazing romance. Pablo and I started seeing each other every Friday or Saturday, and pretty soon, we were spending almost all of every weekend together. It was Pablo's kindness that won me over. He was passionate about his work, doing everything that he could to help people. But he was also compassionate and kind with everyone he encountered.

This was my first serious relationship, so I wasn't really sure how to act. But Pablo was five years older than me, and I found out that first night during our long conversation that he had been with a man for three years whom he had lost to AIDS two years earlier. Pablo helped me learn how to sustain a relationship, making it clear to me that it wasn't always going to be easy. We would have problems and disagreements, he said, but we had to commit to working through them together. He was of course correct. We both had demanding jobs that got in the way of our time together, and I in particular could be irritable and cranky when I was tired or stressed. There were tensions around his family, who lived in Chicago but had disowned him when he came out. But we worked through all of these issues, and more often than not, we made each other happy.

After a little over a year of dating, we decided to move in together. I had just made partner, which meant that I was making a lot of money, and although Pablo had a fairly modest income, he had accumulated substantial investments while working as a banker. So, we decided to buy a condominium together. He was living in the heart of the gay neighborhood at the time, officially called Lakeview but more commonly known as Boystown to gay men (or Wrigleyville to straight guys, because it was near Wrigley Field, the baseball stadium where the Cubs played). We decided to move a little further north to Uptown, which was then an up-and-coming gay neighborhood. It was still close to Boystown, but we could get a larger place, a three bedroom, with a good-sized kitchen, dining room, and living room..

We ended up living there together for almost thirty years, until Pablo died of cancer three years ago. That final year, when I took care of Pablo while he slowly faded away, was the hardest year of my life. I took a leave of absence from work for the last six months of Pablo's life to be his full-time caretaker. Watching him in pain, watching him suffer and decline, was the hardest thing that I had ever done. But I would not have traded that time together for anything. This was the man that I had loved for three decades, and being there to bring comfort in his final days was the bittersweet culmination of our romance.

After Pablo died, I considered selling our condo. We had bought it together, and it had so many memories attached to Pablo that I thought it might feel like a house of ghosts. But my memories of him and of our years together were overwhelmingly sweet, and I did not want to lose them. So, I stayed in our home and was now preparing to turn 65 there, alone.

Pablo and I had built a great group of friends, and they were there for us in our time of need. When he was sick, my best friend, Karen, would come be with Pablo for a few hours so that I could go run errands or just get out of the house. Pablo's sister, Rosa, who had reached out to him after a decade of estrangement and then become very close, would come and read to him. My own sister, Elizabeth, lived out in the northwest suburbs with her husband, but she would come into town a couple of times a month and would clean the apartment or do a couple of loads of laundry. Elizabeth's daughter, my niece, Susan, had recently moved into the Loop, which had become a fashionable neighborhood, and she would just come up to visit and cheer me up. Our friends Dave and Langston and their two kids came by every week to visit, always bringing a meal so that I wouldn't have to cook for a few days.

A few months after Pablo's passing, Karen and my other best friend, Tom, whom I'd known since my law school days and who now lived in New York, took me on a two-week vacation back to Costa Rica. We spent a week at a coastal resort enjoying the beaches, then went to an eco-resort in the interior to explore the rainforest. Before leaving, we spent a couple of days visiting the village where I had taught English so many decades before. Some of the kids that I had taught still lived in the community, though they were grandparents now. It was very special to revisit my past like that, and I was thankful that Tom and Karen had understood that I needed an adventure and distraction.

As I looked back on my life, I appreciated the love that I had known. Pablo had been the love of my life. I looked over at a display of pictures of him and of the two of us that was on one wall. My favorite was one from a few years ago where we were on the beach in Florida, both looking relaxed and happy. I benefited from the love of family and friends as well. I also loved my career. Despite the stereotype of lawyers as money hungry scum, I felt like I had helped a lot of people over the years, and I still took pleasure and pride in helping immigrants get green cards or citizenship or defending people from deportation. My life had been full of great experiences as well. Pablo and I had been financially secure, and we had traveled extensively. We had checked off almost everything on our personal bucket lists - Paris and London and Berlin, Machu Picchu and Easter Island, cruising the fjords of Norway and seeing the Northern Lights.

Since Pablo's death, I had continued to live my life to the fullest. I became more active in the church that Pablo and I had attended, a gay-friendly Presbyterian congregation near downtown. I met up with friends a couple of times a month. I continued to travel as well. Tom and Karen and I now took a trip every year, this summer going to Australia and New Zealand for two wonderful weeks.

What I had not done since Pablo's death, was to date anyone, or even to hook up with anyone. The idea just didn't interest me. For most of our time together, Pablo and I were not really monogamous. Especially when we traveled, we'd find someone to fool around with us in a three-some or foursome. We had stayed at a few gay resorts, in Palm Springs and Provincetown and Key West and had lots of fun when we were there. Occasionally, a few times a year, even back home in Chicago, we'd go on one of the apps to invite someone over. Back in the day, it was Gay.com, then Manhunt, then Grindr. But mostly, we just enjoyed having sex with one another. The frequency of our sex had diminished over the years, but we still fucked at least a couple of times a month up until Pablo got sick. In the last weeks of his life, Pablo told me that he wanted me to find someone after he passed. It had been months since we'd had sex, but to be honest, as I was taking care of him in all of his struggle and pain, sex was the last thing I had on my mind.

"You should go have some fun," he told me one night as I was changing his bedding. "Go out and get laid."

I rolled my eyes. "I don't need to have fun," I told him.

"You've had to shut down your life. You need to live," he said.

"You ARE my life," I assured him. "Being with you is all I need."

Another time he told me that I had to start dating after he was gone. I half-heartedly told him that I would, just to appease him, but I knew that I would not.

Now, here I was more than three years after Pablo's death, looking toward my 65th birthday party in a week and realizing that I still had no interest in dating anyone. In fact, it was as though my libido had died along with Pablo. I didn't look at porn. I didn't even jerk off anymore. Occasionally, I tried playing with myself, because I guess I thought that I should. What kind of gay man doesn't care about sex? But it just didn't interest me. My friend Tom told me that I should see a therapist about my lack of interest in sex.

"Come on, Judah!" Tom had said to me over the phone in an exacerbated voice recently. "Sex keeps you alive! You're going to shrivel up and die if you don't at least jerk off!"

"I'm just not interested," I told him.

Tom was a year younger than me, and he had certainly never stopped having sex. He had dated lots of guys in his lifetime, but he'd never really found love. He sometimes had a boyfriend for a few months or a year before things fell apart. And between boyfriends, and often while he had a boyfriend, he fucked around like crazy. When we went on trips together, he would always disappear a couple of nights to go off and have fun. He and Karen and I might be at a bar, with boys flirting with all of us, and he would manage to wander off with one for the night, while Karen and I laughed and wished him luck. I didn't resent his doing it, and I wasn't jealous. In fact, I was happy for him. But I just wasn't interested in it for myself.

"You're still really sexy," Tom told me. "You could easily get someone!" And, if I might be a bit immodest, he wasn't wrong. I had always taken care of myself. I had been a runner all of my life, and Pablo and I had both gone to the gym regularly. I had a thin but muscular build, never having developed the gut that most men my age carried around. With my British ancestry, my hair had started to recede in my forties, and I'd begun to wear my hair cut very short in my fifties. Even so, I had a nicely shaped head, a strong jaw and eyes hazel that people said were stunning. I had a well-manicured salt and pepper beard that a lot of people seemed to find attractive. Most people I met were surprised to learn my age, assuming that I was at least ten years younger. I knew that I still looked good.

"Judah, you have lots of money. You could buy good sex if you wanted"

"Yes," I responded. "If I wanted. But I don't want."

Tom and I had been classmates in law school. We had met at the very first gay law society meeting, hooked up, and then dated for a week before we realized that we would make better friends than lovers. He was actually the first guy I hooked up with. At the time, we were both tops, and our sex was, frankly, not very good. But we had connected on another level, and we had been close friends ever since.

Tom was flying in from New York on Thursday for my birthday weekend. Several of my friends were planning a party on Saturday. Karen had rented most of one of our favorite restaurants for the night, Big Chicks, which was not far from my home in Uptown. It was a gay bar-slash-restaurant-slash-art gallery. Pablo and I had actually bought a couple of the paintings that hung in our apartment there. We had eaten there so often that we'd become friends with the owner, Lucy.

Pablo was the social one in our couple. He was charming and handsome, with just enough of an accent to seem exotic. He pulled people into his orbit, and they all loved him. I was his slightly awkward husband that they liked well enough mostly because, if Pablo saw something in me, there must be something there. At least, that's what I told myself. Since Pablo's death our friends had remained true, checking up on me regularly, forcing me to come out for dinner, making sure that I didn't become a hermit.

I had met Karen through work. She had started at our firm a year after me, and we often ate lunch together, which is how we became close. She was a contracts attorney and was hard as nails. She only stayed at our firm for two years before moving over to a larger firm where she doubled her salary. Over the years, she had jumped from one firm to another, each time receiving a substantial salary increase, until she arrived at her current firm about a decade ago, where she is senior partner and, as I sometimes joked with her, goddess of all she surveys. Through all of her career moves, Karen and I had continued to meet up once a week for lunch or occasionally dinner. She had adored Pablo the moment she met him, and he had quickly fallen in love with her as well, so we had all been great friends for many years. Karen was fiercely loyal to me, always there when I needed her, never letting me cut myself down.

Karen was also the female version of Tom, moving from one relationship to another, never really settling down. She went back and forth between men and women. Men tended to be intimidated by her strong personality, while most of the lesbians she dated ended up annoying her when they pushed her to get in touch with her emotions. She was rough around the edges and had no patience for softness and sensitivity.

"I can't stand that touchy-feely shit," was one of her common excuses for a break up.

So, most of the time, Karen just hooked up for fun. She was stunningly beautiful. Tall, with just the right amount of curves in her body and thick black hair that she was constantly reorganizing, sometimes pulled back in a ponytail, sometimes flowing down her back, sometimes piled up on top of her head.

I was fortunate to have close friends like Karen and Tom, as well as a fantastic wider circle of friends. Langston and Dave were about a decade younger than me. Pablo had met Langston twenty years ago in a gay volleyball team they'd both been members of, and Langston had met Dave a few years later. We had gone to their wedding over a decade ago, and we were there to help out when they adopted two kids out of foster care, siblings who were 2 and 5 at the time, D'anisha and Tyrell. (They were 10 and 13 now). Pablo and I had babysat the kids a few times when they were little so that Langston and Dave could have a night out. Steve and Andy were another gay couple that Pablo and I had been friends with for ages. Steve had gone to high school with Pablo, and they'd reconnected when Steve moved back to Chicago in his thirties with his partner, Andy. Andy was a designer with a huge personality and a flair for the dramatic, but under the surface, he was very sweet. He was a good decade younger than Steve, but his energy and enthusiasm always made him seem even more youthful. Carl was someone we'd met through his boyfriend at the time, Lewis, who'd been one of my friends, but when they split up, Lewis had moved on while Carl stayed in our circle of friends. I was looking forward to seeing all of these friends and more at the party next weekend. We all got together a couple of times a year for dinner at one of our homes.

The phone rang and startled me out of my maudlin reminiscences.

I saw from the caller ID that it was my sister, Elizabeth. She called almost every Sunday night to check in.

"Hey, sis," I said.

"Judah. How are you?" she started.

"I'm good. Just finished dinner." Pablo and I had both enjoyed cooking, and after he died, I made a point of still cooking myself good, healthy meals rather than ordering out all of the time. I often cooked a big meal on Saturday or Sunday, a stew or casserole that I could eat as leftovers a few times during the week. Today, I had made a lovely cioppino, a seafood stew, with fish and shrimp and clams. It had been one of my recipes that Pablo loved best.

"Larry and I are looking forward to the party on Saturday."

"Me too," I told her.

We chatted for a while about various things. Elizabeth was a middle school teacher, and she loved to tell me funny stories about things that happened in the classroom. It was September, so she was just a couple of weeks into the new school year, and she updated me about her students this year. I talked a bit about a challenging case that I was dealing with.

"So," Elizabeth began, in a voice that I knew meant that she was shifting gears. "Susan has a friend that she's hoping you can meet."

"Okay?" I said tentatively, wondering where this was going.

"They were in school together at Columbia, and he's just moved to Chicago." She paused a moment.

"He's starting as a lawyer at a big firm here, and he's gay, and Susan thought that maybe you could give him some advice on being a gay lawyer or something."

"How does she know someone who was in law school?" My niece, Susan, had earned a PhD in chemistry at Columbia and then had come back to Chicago to work for a pharmaceutical company.

"I don't know. He did some sort of joint degree or something. She thinks you might have good advice for him."

I thought it amusing that my niece believed I would have any useful advice to impart on someone so much younger than me, but I was slightly flattered. "Okay, tell her to connect him with me."

We chatted a bit longer, then hung up, and I set about washing dishes and cleaning the kitchen. Just as I was finishing up, my phone rang again. This time it was Susan calling.

"Hello?" I said as a I picked up the phone.

"Hey Uncle Judah. Mom tells me that you're willing to meet my friend, Julio."

"And hello to you too. I'm doing fine, thanks," I said, needling her gently.

"Yes, yes, yes. How are you? Hope everything's good and all that." As a scientist, Susan was sometimes very focused, with little patience for formalities. "So you'll meet him? He just got to town and he starts his new job in a week and he's very nervous about it."

"Of course I'll meet him if you want me to. Julio, you say?" I said, pronouncing his hame in the Spanish way, like Hulio.

"Julio," she said, "With a hard J. He's Brazilian."

"You know you could have just asked me yourself," I told her.

"Well, I didn't want to impose," she replied.

"So having your mother ask me is somehow not an imposition?"

She sighed. "Don't be difficult, Uncle Judah."

I laughed. "You know I love you dear."

She explained that they had met in one of her law classes when he was working on a joint JD/PhD. He'd just finished his dual degree and had been hired by a large Chicago corporation to work on intellectual property law. He'd move to town last week, and she had met him for dinner on Friday. She's the only person in Chicago he knows, and he's very nervous about how he'll be received as a gay man in Chicago. He was wondering whether he should stay closeted.

"`Well, my uncle can give you advice on that,' I told him."

"I guess I can," I said.

"Great! So, can you meet him this week? He starts his job next Monday."

"Okay. Sure," I said. "Give him my contact information."

"No," she said. "I'll send you his number. You reach out to him."

I agreed, and we hung up. A minute later my cell phone pinged as she sent me Julio's number, so I texted him.

  • Hi. This is your friend Susan's uncle Judah. She said you might want to chat.

Only a minute later, I got a response.

  • Oh yes please sir if you don't mind. I could use some advice.

We texted back and forth a bit, and I agreed to meet him on Tuesday for lunch at a restaurant near my office in the Loop.

It was still early, but I went ahead and got ready for bed, planning to read for a while before going to sleep. I brushed my teeth, put on a pair of pajama bottoms, plugged my phone in to charge, then climbed under the covers. I opened the novel I was reading, but I found myself rereading the same page over and over, so I put the bookmark back in and set it on the bedside table. I lay there for a while, thinking about my past, about my upcoming party, and now about this strange request from my niece. What good advice could I offer to a young attorney just starting out? I'd been at it for so long that I wasn't sure I even remembered how it was like at the beginning. Maybe there were some specific questions he had that I could answer.

Thinking about all of these things, I drifted off to sleep.


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Next: Chapter 2: Second Chance 2


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