I Thought These Guys Were Out of My League—So I Asked Them About It

Though I’m a huge baseball fan, I’m not really sure where the phrase “out of your league” originated. Come to think of it, I’m not even sure it has anything to do with baseball [Editor's note: It does; it has to do with the fact that there are various baseball leagues (minors and major) stratified by ability and professionalism], but I do know that I have viewed almost every man I’ve ever been attracted to as out of mine. Out of my league is my home base, the place I operate from. It’s like a switch box inside my brain that sends me signals at different times to remind me that I am not on the same level as these men. I’m going to the same schools as them, I’m working at their companies, I’m drinking the same tequila, but it never feels like we’re in the same stratosphere.

I’m 27, and the first time I’ve ever felt confident was only two years ago. That was when I dedicated myself to writing, and actually got something published. Until then, I’d spent the majority of my life not liking who I was, and I relied on self-deprecation to deflect from my insecurities. But writing made me feel worth something, and I attempted to use that build up my own confidence. It’s an everyday process: Confidence in my work is one battle, confidence with potential romantic partners is a separate one that, incidentally, feels like scaling a mountain of garbage bags.

A few months ago, my mind landed on a random guy I knew from college. I immediately reminded myself that he was out of my league...and then paused. I thought of the last guy I had feelings for and, like an instinct, reminded myself that he, too, was out of my league. I suddenly realized that I repeat this thought process for every person I’m attracted to. With my newfound self-assurance, I decided to dig in: Why do I do this? Are these men actually better than me, or had I just been putting myself down? And what metric did I even judge “out-of-my-league-ness” by?

So, in the spirit of someone who can take ownership of being insecure, I decided to seek these guys out. I wanted to learn about these people I’d shoved out of my realm of possibility to see if my newfound confidence cast them in a different light. I was excited when five of them agreed to talk: They’re bankers and managers and other professions that your grandparents would be impressed by, and they look different and believe in different things and have different interests and passions. But what they share is that, at one point, I labeled all of them too good for me. It was time for a discussion.

Max

Age: 27
Occupation: Finance at a big firm
How we met: The University of Scranton, where romance thrives
When I decided he was out of my league: Last summer when he asked me to grab drinks
Why I thought he was out of my league: In college, women seemed to line up around the block for Max. He’s tall, handsome, has a good job, likes books—I could keep going about his excellent qualities, but I’m starting to sound creepy and my mother is going to read this (she’s already not thrilled).
Fun fact: He posted a photo with an alpaca in Peru this summer and I was unnerved.

Over artichoke dip at a bar in Midtown Manhattan, Max and I had a shockingly open conversation. We theorized about the idea that maybe for some people, the insidious self-doubt one develops in middle school can linger for years afterward. We talked about how we’ve changed since college. Max said he was a different person then—younger, drunker, more reckless with the emotions of other people. He used to be someone who would rely on women for emotional support without giving them what they wanted or needed in return.

And Reader: I’ve never in my life heard a man openly admit to leading women on, so I give Max credit for that.

He says he’s growing and he’s constantly putting in the work to be better than he was before. Back in college, I never would have taken Max for someone who struggles with self-confidence. He’s over six feet tall! He has a job in money or whatever! He speaks different languages! But when I asked him about where he gets his assurance, he looked at me and said, “I wake up, and there are days where I’m genuinely like, ‘I am the ugliest human being in the world.’”

It felt like a slap in the face in the best possible way. Maybe I needed to hear that someone whom I’d placed on a higher pedestal could feel the way that I’ve often felt. Overall, a good conversation.

Will

Age: 29
Occupation: Project Manager
How we met: Will sat next to me in freshman year theology
When I decided he was out of my league: The moment Will sat next to me in freshman year theology
Why I thought he was out of my league: He’s the quintessential guy in college you ran into at lunch who made you nervous-giggle.
Fun fact: I have no idea what grade Will got in our theology class. I keep forgetting to ask.

I was especially nervous to meet with Will because, if I’m being frank, he has a perfect face and I was afraid to speak into it. Will expressed that he considers a woman out of his league only when he hasn’t gotten the chance to know her. “There’s this feeling that she’s got experiences that I don’t have,” he says. “By being familiar with a thing I’m not familiar with, she’s [in a way] a step above me, on a small scale.”

I asked him about confidence. “I take this active step in saying, I’m going to be confident, then it almost makes itself happen after that,” he said. It sounds silly, but I was once again surprised to hear someone like Will use the word “active” in relation to his experiences with self-assurance. Before these conversations, I really did believe that they were just confident because of who they were, both on paper and in real-life. And I was who I was—a frazzled troll doll of a human who is just happy to be here. With Will, I was already learning that this isn’t always the case.

Anthony

Age: 26
Occupation: Medical Student
How we met: When we were kids; our moms are best pals
When I decided he was out of my league: A few summers ago, our families vacationed together. I hadn’t seen him in years, probably since we were children
Why I thought he was out of my league: Anthony is athletic, smart, and one of the kindest people I’ve ever known. He’s funny and he played hockey and he seems to have a handle on things.
Random fun fact: He has a dog named Sunshine!

Turns out, Anthony struggles with confidence, too! (Noticing a pattern?) But his was more professional: Anthony is studying to be a doctor, something he previously thought he was incapable of doing. “I thought it was way out of my reach,” he said. “I automatically assumed I was someone who was unintelligent and didn’t have the work ethic, and someone who didn’t have the capability to excel or get to medical school.”

I asked Anthony about his initial reaction to hearing that I believed he was out of my league. He said the overall sentiment didn’t exactly make him feel good. “It was a little bit of a shock, I had never viewed myself as that, as somebody that was unattainable,” he said. He appreciated the project though, and whatever I was trying to achieve in asking these questions. He closed our conversation with, “More people should welcome the need to find answers to things, to find answers to difficult questions. I don’t think enough people are willing to take the necessary steps to figure out those answers.”

Claudio

Age: 27
Occupation: Registered Nurse
How we met: We went to neighboring high schools
When I decided he was out of my league: Around the time he expressed interest in wanting to date me
Why I thought he was out of my league: I had absolutely no self-esteem and I just couldn’t fathom someone being interested in me
Random fun fact: In high school, my friends and I invited Claudio and his best friend over on a random weekend to play video games. My dad came home unexpectedly and I hid Claudio and company in my closet. Memories!

Claudio was my first-ever boyfriend! We dated our senior year of high school. I couldn’t believe he actually wanted to date me—I couldn’t believe anyone wanted to date me. At age 17, every other sentiment I muttered was a joke about how I was either ugly or stupid.

Claudio was funny, driven, and nice to look at. (He is still all of those things!) We hadn’t spoken in about a decade so I had no idea what to expect, but he talked a lot about his job as a nurse and how he didn’t pass his licensing exam until the third try. “Anyone who says they’ve never felt unworthy is lying,” he said matter-of-factly. He also had a profound point about how, in our culture, it can feel like there’s absolutely no room for mistakes. “There’s an overwhelming sense of making sure you never look stupid on social media or even say anything dumb in real life,” he said. “It’s like we’re not allowed to make mistakes anymore, because it’ll be hung over our heads for the rest of our lives.”

This interaction in particular made me think about how to reconcile who I was when I was younger with who I am now. I’ve gone from a teenager with a palpable and all-consuming lack of self-esteem to an adult who recognizes that I need confidence to survive in this world. I have a lot of work to do, but 17-year-old me would not recognize 27 year old me—a woman who claims space and actively tries to be present and confident. For that, I’m very grateful.

Leo*

Age: 27
Occupation: Alumni director
How we met: Through a mutual friend.
When I decided he was out of my league: As soon as I met him. Leo is brilliant and essentially the poster child for “man you bring home to your mother to ensure that she will break out in violent sobs of relief and joy.”
Why I thought he was out of my league: Please see above.
Random fun fact: He both respects and encourages my love for telling men on dating apps that I like their bowties.

When I first asked Leo about someone being out of his league, a specific instance came to his mind. As I previously stated, Leo is smart. He went to a really good high school, he went to a really good college. When I heard in passing that he became a Fulbright scholar, I felt zero percent surprised. In our conversation, however, I learned Leo didn’t have the assuredness I’d given him in my mind. Upon moving to another country for his scholarship, he says that he thought, What in the world did I do to deserve this?

I never knew Leo immensely well, but I remember him from 10 years ago. He was intelligent, kind, and had a smile that made mere mortals melt. Leo told me that he grapples with body insecurity; how, if he has to change in a public setting, he’ll do it as quickly as possible. Leo is someone I look at with great reverence, and I’m grateful to him for expressing such vulnerability in his feelings of unworthiness regarding his mind and his body.

With my social media and culture obsession, I am constantly putting myself into a different category: There are the smart, attractive people, and then there’s me. Leo reminded me that I don’t know these people, who are likely categorizing and battling themselves in their own ways. I don’t know the inner workings of someone’s soul—no matter who they are or how attractive they are. I do not have a monopoly on self-doubt.

After these interviews, I felt like I had reached my vulnerability cap for the year. I gave each of these men a ton of power in the past, a power that none of them even asked for. For years, a chorus sang to me in my head: “You’re ugly! You’re stupid! You don’t deserve a good thing with a good person!” Now, I feel a bit more equipped to tell that chorus to shut up.

It’s not like this project was a silver bullet: I still feel self-doubt to my core. But I’m trying to overcome it, and hearing that these people are too made me feel less alone. I have to accept the ways I’ve hated myself and confront my tendency to do so. Mostly though, I need to believe in myself the way I’ve believed in others, to actively work toward being the woman I want to be—someone confident in her belief that she deserves good things and good people. No more conversations about metaphorical leagues.

*Names have been changed by request where indicated