WHEN WE WERE in high school, Jennifer Tejada was a cheerleader and had everything that came with being one of the girls who’d stand in front of the student body before pep rallies shaking her pom-poms and chanting about school spirit. She was beautiful and popular, and I worshipped her from the other side of the auditorium.

So I was surprised when she responded to my friend request. Once she did, I started cyberstalking her. Jennifer lived in Chicago, had two kids—a boy and a girl—and was a doctor like her dad. She’d vacationed in Mexico; there was a nice picture of her on the beach, tanning on a beach towel. She was married, though (and here was the interesting thing) I didn’t see any pictures of her husband—none of those duo selfies couples post of themselves at ball games or national parks. It had occurred to me her husband might be the one taking all the pictures, or the lack of husband photos could be a subconscious thing. I wasn’t speculating as to why there weren’t any photos of him, but I was hoping it had something to do with her not being happy in her marriage. In my experience, when women aren’t happy in their relationships, the first thing to go are the pictures of their spouses. Basically, they didn’t want anyone to know they were married. How did I know this? When I became a certified car salesman, I also became a quick judge of people. I was basically a psychologist without the fancy degree and student loan debt.

Honestly, I didn’t really know a lot about Jennifer’s life except she liked margaritas, her favorite TV show was Grey’s Anatomy, and her favorite book was some self-help best seller I’d never read. But really, how much can a person change in twenty years?

I didn’t meet Jennifer until we were in high school. She came from a good family. Her dad was a doctor in town—a heart surgeon who drove a BMW. Jennifer’s mom drove one too. When it came time for Jennifer to drive, she inherited her mom’s car, and her mom got a brand-new BMW 750i. Despite being rich, Jennifer wasn’t pretentious and didn’t rub it in anyone’s face. Our school’s student body came from mixed incomes. There were a few rich kids, a few poor kids, and varying degrees of middle class. Some people could get snooty, thinking they were better than everyone else because their dad was a stockbroker who got in on the first dot-com boom early, bragging about summer vacations in Paris—this was Jennifer’s best friend, Paige Buchannan—but Jennifer just seemed to float over all of it.

In school, Jennifer was always quiet. She was content to hang out with her friends, and that was enough for her. She was kind too, always saying hi to me even though she didn’t have to. Since I was on the football team and she was a cheerleader, we ran in similar circles; we’d be at the same parties on Friday nights. I’d like to say I was the big man on campus, but I was pretty quiet too. I wasn’t overweight—not like now—but I was pretty husky. I was a fullback, big enough to run over the opposition. At these parties, we’d say hi to each other and talk a little bit, nothing serious or memorable. At least not for her. It was memorable for me. Every time she’d walk away, I’d feel like I’d embarrassed myself in some way, then I’d go refill my cup from the keg out back. This was the pattern at these parties: I’d fill up my cup, hang out in the kitchen or by the pool or wherever, then I’d try to work up the courage to talk to Jennifer, usually by drinking more. When I’d finally get to a point where I could talk to her, she’d be laughing with her friends or leaving with this college guy, Chad, on the few weekends he was back in town.

One of the main reasons I never asked Jennifer out, aside from the fact I was terrified she’d say no and everyone would make fun of me for thinking I stood a chance with her, was because she was dating this guy Chad. Chad was two years ahead of us, had graduated, and was attending Ivy Tech in Fort Wayne. There was an Ivy Tech in Bloomington, but I heard Chad couldn’t attend that one because of a DUI court hearing no-show. Once they broke up, every guy in school set their eye on Jennifer, but she was just out of reach.

In those rare moments when she was by herself, and I finally had the courage to talk to her, I’d be too drunk to string two words together. Usually, I’d just go and pass out in a chair or throw up in some kid’s backyard somewhere.

I was thinking about asking her out, like really thinking about it. I wanted to take her to the drive-in, pull up in a brand-new Acura, straight off the lot. All the other kids would see us together. We’d be the talk of the lunchroom on Monday. That was plan A. Plan B was we’d just hang out in my basement watching movies or playing pool with a bunch of friends. I figured she’d be more inclined to hang out if she knew it was going to be a group thing. Then one day, I was given the opportunity to talk to her without all of her friends around or me being too drunk to talk, and I blew it big-time.

For some reason, we hadn’t had any classes together. It might’ve been because Jennifer was in all the AP classes with Harry and his buddy Timothy. But, after years of not having a class together, junior year, we had Spanish III. My dad made me take Spanish because a lot of the guys who worked in the shop were from Central America, and he wanted me to be able to talk to them once I started working there. The Spanish III teacher, Señor Ortega, was notoriously a dick. He was one of those teachers who hated being a teacher because he thought he should be off doing something else, like writing this book about Guatemala he always said he was working on.

One day, I showed up and there was a new seating assignment; teachers liked to mix it up every nine weeks so they didn’t get bored staring at the same faces all the time. Ortega placed me in the second row on the far left-hand side of the room, and right next to me, he placed Jennifer. I’d been thinking about sitting next to her all semester, planning out what I’d say, how I’d try to be cool but not too cool; how I’d be nice but dangerous; how I’d be charming but not creepy; how I’d be the type of guy she’d say yes to hanging out with. I was thinking I’d get to spend a nice hour with her every day and establish the basis of our friendship, because up till then, I hadn’t had the courage to have a conversation with her that didn’t involve me seeing two of her. These fantasies died when I looked in my book bag and saw I’d forgotten my book at home.

Ortega said to pull out our textbooks and turn to page whatever, and right away, I knew I was in trouble. I raised my hand and said I didn’t have my book with me. I started sweating like crazy because I had very few options: either Ortega had an extra book somewhere or I’d have to share with Jennifer. I panicked. The thing I’d been hoping for all year was about to happen; I’d be forced to slide my desk over and talk to Jennifer. It’d be in another language, but I’d still be talking to her. Ortega had to have seen me turning red. I was hoping he’d be understanding, compassionate, and say, “Yeah, I have an extra book up here for you.” I leaned forward, almost willing there to be an extra book in his drawer. Instead, he grinned and said, “Share with the person next to you.” That evil son of a bitch knew what I was going through, and he fed me to the wolves—or wolf, who was looking super fine in the flannel shirt she got at a department store in Chicago.

All the kids in the class were looking at me, wondering what I’d do. My friend Jerry stared at me, knowing I’d had a massive crush on Jennifer since our freshman year. And what did my dumb ass do? I turned around and asked the person behind me, Kevin Johnson, if I could look off him. He was a good kid and let me share. I think he was thinking he’d have done the same thing, both of us being pretty introverted around girls. He was also husky, like me, so he understood that sometimes embarrassing yourself further is the only way to keep from really embarrassing yourself.

Sadly, every day after that, I remembered my book.

I’d thought about that day a lot since then, thinking about what I would have done differently. It was one of those defining moments in life where you realize, this is who I am. I’m the guy who was so scared of girls that when faced with an opportunity to spend time with my dream girl, I turned around and talked with Kevin Johnson.

But really, there’s no way she would have ever gone out with me. I had such a low self-esteem when it came to girls, I didn’t think anyone would want to go out with me. To mask this, I was a jerk. Whenever I was in the hall between classes with my football buddies and we’d see some kid who was considered smart, someone—usually Billy Jacobs—would trip him or knock his books out of his hands. Everyone would laugh because we could. And sometimes, I’d be the one doing the tripping. I was cocky, arrogant, everything a woman wouldn’t want in a guy, but guys think they do. What girls like Jennifer didn’t want was a guy who doubted himself and was a jerk to everyone. And that was me, all the time.

High school was one of those periods I wish I could go back in time and change.

But I couldn’t. What I could do was try to show Jennifer I wasn’t the same person I was when we were kids. And that’s why I messaged her. Well, one of the reasons, anyway.

She responded almost right away.

Dennis, OMG. (I’m guessing she got that from her kids.) It’s been so long. How are you doing? It looks like you’re doing well running the car dealerships. I think my dad just bought a car from you guys. (I had to look this up, but her dad did buy a BMW 540i Sedan from us sometime last year.) Things are going well. I’m in Chicago working in pediatrics. (She worked with kids; how incredible is that?) I’ve been here since we graduated. I went to DePaul for my undergrad, then Pritzker School of Medicine for my MD. (Pritzker was one of the top schools in the country, tough to get into.) I have two kids, Joey 10 and Katy 7. They take up most of my time, taking Joey to Krav Maga and Katy to ballet lessons. I’m not a real fan of Joey learning to fight, but he was bullied last year, and it gives him confidence. I work at a private practice, a peds clinic. I’m one of five doctors there. Some friends and I opened it a few years ago after we grew tired of working in a hospital, dealing with the red tape. (A small business owner, probably rolling in cash.) It’s been very rewarding developing long-term relationships with patients. But other than that, I haven’t really been doing much, just being a doctor mom. What about you? You were going to play football for Indiana, if I recall. How did that work out? (I was surprised she remembered this.) Let me know what you’ve been up too. So good to hear from you. Talk to you soon.

There was a lot to unpack there. First of all, she remembered me. That was a miracle right there. We went to high school with about two thousand kids, and I didn’t remember half of them, even though half of them still lived in town. But out of all those kids, she remembered me.

Second, she asked me to write her back, to tell her about what I’d been up to. That’s a tall order, because I couldn’t tell her I’d been thinking about her every day for twenty years. I’d have to build up to that.

Third—and this was the most important thing—out of all the things she mentioned in her message, she didn’t talk about her husband. Most people, if they’re married and have a family, say, “We did this,” or “We went here.” She kept saying “I,” like the guy wasn’t even in the picture.

So I messaged her back. I took my time and wrote out a message I thought represented where I was in life and who I was as a grown-ass adult. I spent hours drafting and redrafting it. It needed to be perfect. I had to show her I wasn’t the same person I was when we were kids; I needed her to know I’d grown. When it was ready, I sent her a message I thought showed just enough interest while remaining cool, like I wanted to talk but didn’t really care if she responded or not because I had my own thing going on.

Jennifer, glad to hear you’re doing well. I’m surprised you remembered about the football thing. That didn’t really work out like I’d hoped. I was a walk-on at IU for about a day, then I saw what talent really looks like, and I hung up my cleats. After college, I went to work for my dad full-time. When he passed, I took over the dealership, opened a couple more. One caters to high-end clientele—or folks wanting to present themselves as high-end. We always wind up selling a bunch of cars whenever the pro football and basketball drafts roll around. Bloomington has changed a lot since we were kids. It’s not even funny. I’m sure you notice it when you come back to visit your folks. But it’s still a good town. I never married, don’t have any kids. My life is pretty boring. Something crazy happened the other day. You remember Harry Erickson. He might have been in some of your classes. His house burned down. Had to help him with that. Not the burning part. I don’t own a flamethrower or anything. But yeah, it’s just boring old Bloomington. Good talking to you again after all these years.

And that was it. That’s all I said. I didn’t know why I said that bit about Harry. I think I wanted her to know that even though I’d made it big, I still looked out for those less fortunate than myself. She could ask me how I knew Harry since I didn’t hang out with him in high school, and that would lead to me having to talk about Amanda, which could cause some problems down the road. And that’s exactly what she did in her next message.

Of course I remember Harry. He was so sweet and quiet. He was in my AP calc, AP physics, and AP chem I and II classes. I hope he’s okay. How do you know Harry? Will you offer condolences on my behalf next time you see him?

I had no intention of telling Harry I was speaking with Jennifer or that I was using his house burning down as a way of getting sympathy. But I did write her back.

I know Harry through a mutual friend, someone we both know from college. He’s doing okay. He’s staying with his daughter right now. He has a daughter in college. Can you believe that? Crazy! She’s a good kid, takes after him. Hey, this is gonna sound crazy, but we should exchange numbers—you know, in case I’m ever up in Chicago, or if you’re ever down here and want to hang out. Talk to you later.

The part about the phone number was a total long shot. It’s something I never would have had the guts to do when we were kids. In high school, I’d have worried her friends would laugh at me, then get the whole school to laugh at me. She’d always been out of my league, and it didn’t look like that had changed. Also, she was still married, so when I asked her for her number, I never thought she’d give it to me. Honestly, I thought she’d stop talking to me all together. But she sent me her phone number, including this message with it:

Dennis, here’s my number. I know you’re seeing someone. I still have friends who live in Bloomington. But I understand that sometimes you can be with someone and not be happy. If you ever want to talk, I’m here.

I felt a little shitty for misleading her; she didn’t deserve that. I wanted more than anything to have an honest relationship with her, and I should have known I’d get caught. I still saw Paige Buchannan around town. I’m sure she ratted me out.

But after all that, she still didn’t say she was married. Her next-to-last sentence made me wonder if she wasn’t happy either. I understand that sometimes you can be with someone and not be happy. So maybe she wasn’t happy. Maybe her husband did something—cheated on her, took out credit cards in her name, got several DUIs. It could have been anything. But whatever her husband’s mistake was, maybe it would give me a chance to correct the mistake I made twenty years ago. It wasn’t a mistake necessarily; it’s just that I didn’t take a chance when one was presented to me. But now, things were different. Now I was ready to take a chance.

I waited a few days to let her think I was thinking about her offer. Then, I texted her.