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I Was a Creep

Confessions of a Recovering “Nice Guy”

This is Nice Guy Syndrome:

Boy: Will you date me?

Girl: No thanks.

Boy: Why nooooooooooooooootttttt I'm such a nice guyyyyyyyyyyyyyy why do women always go for assholes T_T

Alternate title for this article: “Dr. Niceguy or: How I Learned to Stop Whining and Burn the Fedora”

Alternate title for this article: “Dr. Niceguy or: How I Learned to Stop Whining and Burn the Fedora”

Nice Guy Syndrome is when men, often timid ones, feel like they are on the losing end of the romance game because they are "nice." It’s a pretty well-trod internet truism that most men with Nice Guy Syndrome aren't really nice guys, they just compensate for their motives with “niceness,” sometimes being in denial about what their motives even are.

When you break Nice Guy Syndrome down to its basest components, you see that these "nice guys" frequently treat women as though they are gachapon machines wherein affection, kindness, favors, compliments, gifts are given and sex, dating, intimacy, all of the above are the rewards for playing. Just because you are nice to someone doesn't mean that they are obligated to turn around and give you a blowjob. The reasons people have for feeling romantic/sexual arousal are often complicated. Yeah, being nice to someone may endear them to you, but it's not a guarantee.

At its absolute worst, this entitlement pairs with a demonization of women in some sometimes subtle and, more often than not, noxious ways. There is a tendency towards coercive and manipulative behavior, frequently manifesting in the presentation of sexless “just doing good deeds” when sexual desire is the primary motive. There is a tendency towards constant self-martyrdom (read: victimization) and condescension: “Why is she with him? She doesn't know what she actually wants. Why are women so blind?” And thus, a “nice guy” will answer the question, "Why doesn’t she like me?" with "Because she doesn't know what's best for her," therefore granting permission to continue his creepy behavior. It can't be that she’s just not into you, no, she just hasn't seen how she must be into you. More unsolicited flowers and offers to wash her dishes will definitely help her make that discovery.

May Hollywood forever burn in hell for… well, infinite reasons, but in this article I damn Hollywood for depicting the height of romance as men who get the girl by wearing her down until she says “yes.” May every party club anthem burn for the same reason (although may they primarily burn for all being shit).

There's a lot of casting of external blame with Nice Guy Syndrome. It’s the nature of women. It's feminism's fault. Or political correctness. Or the shallowness of others (often said by blokes who won't settle for anyone less than a supermodel). There is no shortage external scapegoats for “nice guys” to throw their blame on. God forbid they sling it on their own miserable selves.

This ye olde self-righteous condemnation is good and all, but it is merely a framework with which to prop up the real topic of this article: stories about my history of botched non-romances framed in the lens of Nice Guy Syndrome. It’s my past self I’m condemning, you see.

You see, in eighth grade, I fell for Nadia…

We can’t start there. We have to go all the way back.

I used to suffer from Nice Guy Syndrome to a degree, the full extent of which I will leave for you to decide once you make it to the end of this surely too long article. Thankfully, my natural tendency to always blame myself when things don't go my way means that I never engaged in the truly toxic forms of Nice Guyness. I always played the internal blame game. My answer to the question, "Why doesn't she like me?" was “Probably because I suck. Or because she likes someone else. Because I suck. I'm nice. But also I suck.”

My optimism paired with my frequent inability to correctly read people and situations often led to a simpler yet more insidious question with a more insidious answer: “Does she like me?” to which my answer was… well, that’s this article. The distinction between “Why doesn’t she like me?” and “Does she like me?” seems like a matter of petty semantics, but trust me, they are worlds apart.

Ambiguity, for one reason or another, frequently causes the steam engine that is my brain to melt into a malfunctioning slag heap.

A lot of these stories can be chalked up to the folly of youth. And yet - okay, here’s a phrase I’m going to use once and never again because it is overused and misused to the point of meaninglessness - toxic masculinity plays a role as well. How much can mistakes in this vein be attributed to being young and dumb? How much to the way men are socialized? The line is unclear. Maybe by examining my own misdeeds, we can take a look at where youthful folly and socialization influence each other and see what conclusions can be teased out.

These days, I'm in a loving relationship that I wouldn't trade for anything. I'm many, many, many years removed from "nice guy" Drew. Even though I didn’t do anything truly harmful (there is no content warning required for this article), I’m ashamed all the same, all these years later.

You see, in eighth grade, I fell for Nadia…

Let’s have a laugh at Past Drew’s expense, shall we?

Origins of a Dweeb

(Oh, and you can believe that all these names have been changed. Don't worry, Layla. They won't know it was you.)

I have always had a bit of the sappy romantic in me. When I was like, three to five, I was one of those little boys who asked girls to marry him. There are a lot of little boys who do this, but why? Sociologically speaking, it’s because -

Ah fuck it, let's skip ahead a bit more.

My first whopper of a crush came in fourth grade and it was for a girl I'm going to call Cecilia.

What’s most amusing about this first crush is that it came about because a couple of my friends were talking about their crushes (as you do in fourth grade) and I decided I needed to have one too.

I said: “I have a crush on Kristen.”

My friend said: “You can’t have a crush on Kristen. I already have a crush on Kristen.”

“Oh. Okay,” I thought for a second. “What about Cecilia?”

“Yeah that’s okay.”

And thus I began to pine after Cecilia.

(This is a funny event in my life because it shows how spineless and easily swayed by other people I was at ten years old and it’s especially funny because I am in no way like this anymore, no siree, I never change my opinion on a dime because someone told me to, I never say that I want something and get told “no” and just shrug and go “I guess that’s the way things are,” I never let people convince me to do things I don’t want to, I never -)

Although it was an arbitrary selection, I did have genuine feelings for Cecilia based on… well, nothing. We rarely spoke to each other. Our friends weren't friends. and she was the quiet sort.

This crush lasted years. Fourth through sixth grade.

There are three events of note that happened between the two of us. For the life of me, I cannot remember the order they happened, but I think they all occurred in sixth grade, so instead we’ll go from least incriminating to most incriminating.

Item the first:

My friend and I were on the asphalt during recess, chatting, probably about Yu-Gi-Oh. Same friend, by the way, who said I couldn’t have have a crush on the same girl as him. This was not a toxic friendship at all and definitely did not contribute to neuroses I have as an adult.

What is important is that Cecilia and her friend came up to us.

Her friend and my friend talked. I stood back, fidgeting and feeling more nervous than a family values senator whose mistress was threatening to tell the press about her abortion. It was as if I had jumper cables clamped to my skinny waist. I was all nervous because at any second someone could connect the car battery. Then Cecilia’s friend said, "So I hear Drew likes Cecilia…”

The car battery connected. I hopped a foot into the air, ran, and blacked out. When I came to, I was on the other side of the playground, hiding behind a brick wall. I stayed there until recess was over.


Item the second:

One time, Cecilia called me on the home phone and I flipped the fuck out.

I was reading (probably Eragon - remember Eragon?) and the phone rang. My mother picked up and she gave me this… look… and said, "It's for you."

It was the sort of look that a second grader on the playground would give another second grader. The sort of look that says, "I know you like a person, I know who he/she is and isn't this so juicy, ooooh you like someone."

You know this look. That mischievous smile. The raised eyebrow.

My mom passed me the phone. I was perplexed, both not understanding why the caller would want to talk to me nor comprehending my mother’s body language.



“Um. Who are you?”


"Uh..." I could tell it was a girl's voice. It couldn’t be hers… no... she wouldn't… on the landline? In front of my mom? No… she would never... "Um…is this…is this Aileen?"


Pictured: My memory

Pictured: My memory

"Is this, um, Patricia?"


Gulp. "Is this... Cecilia?"


And then I blacked out.

I know that I fled upstairs with the phone. I know that we exchanged a few awkward words. I think it was about homework or something? And then that was that.

I regained consciousness when I crawled back to my book, undoubtedly redder than Satan's rash-ridden scrotum.

So maybe Cecilia was into me too. Looking back, that's a pretty firm maybe.

But lil' ten year old Drew was mostly just freaked out and didn't know what to do, so he interpreted the phone call at face value - “she just wanted to know about the homework or whatever.” My mom tried to tell me that my face value assessment was wrong, but my skin was in the process of turning inside out from the embarrassment of it all, so I wasn't listening.

Item the SHAME:

For a while, our class seating arrangement had the two of us positioned in a way where she was in my field of vision of all times.

I frequently just stared at her when I thought I could get away with it. Which was most of the time. When she would look my way I'd pretend like I wasn't just looking at her, in fact I had never looked at her in my entire life, who even are you, I’m just so gosh darn interested in this lecture on fractions. Heart thumping like a taiko drum, I’d analyze whether or not her look back meant that she was reciprocating my feelings or judging me.

I’ve always had a difficult time discerning how people really feel towards me. This led to a situation a month into college where the guys I thought were my friends sat me down and told me that I was a fucking weirdo and needed to stop hanging out with them. Romantically, this means I have trouble discerning if someone is into me, or if I'm reading into everything they do because I want them to be into me.

Hey, at least I had the self-awareness to even consider the latter.

Incidentally, whoever it was that introduced me to the concept of "playing hard to get" should get all the bills for my therapy.

We’ll come back to that one. Not really relevant to Cecilia and I's situation.

So, I could stare at her whenever I wanted. Stealing glances at people we are attracted to is a perfectly normal thing to do. These weren’t glances, however, these were minutes-long stares. I know that's really creepy as hell, but I can can give kid me some slack for being in sixth grade and not knowing what the barn-fucking cattle-dick he was doing. All he knew was that he liked a girl and had no idea how to properly admire someone, let alone express said admiration to them.

But then we had the sixth grade version of sex-ed.

Guess who did a lot of staring? At Cecilia?


Look, I was in sixth grade, it wasn’t a predatory sexual thing, I swear. At that age, all I understood was that sex and love were connected and I totally thought that by staring at her and her staring at me, that would mean some sort of... romantic… thing...

It made sense to sixth grade Drew, okay?

Oh my god, I did a totally creepy thing, didn't I? No amount of explaining intent is going to change that. I must have made Cecilia so uncomfortable.

And so my first crush sets the theme for all to follow: Drew doesn’t know what he’s doing and makes a huge ass of himself.

You may notice: there isn’t anything that happened between me and Cecilia that I can chalk up to Nice Guy Syndrome, even including the sex-ed bit, but it sets the stage. The timidness, the not being able to decipher ambiguity, the constant analysis, the strange sideways plan of getting her to like me - those were there from the start. I was too young to be desperate, but once desperation gets layered onto these stories… well, you’ll see.

My interest in Cecilia petered after sixth grade. I wanted to begin middle school with a fresh start. That’s perhaps the dumbest sentence I’ve ever written, but it was true.

My original plan with this was to tell these stories in chronological order. But the next girl I fell for chronologically also has the most mortifying story attached to her. I can’t tell that one yet. I just can’t. Telling it now will make everything that comes after seem like an anticlimax. Nadia is the climax of my Nice Guy Syndrome struggle, even though she’s the second girl I fell hard for, even though I would continue to display “nice guy” behaviors. Her story contains shades of all others.

Let’s get non-linear.

Before my Current Relationship, I’d Gone on Only One Date in my Whole Life

This is like, the thinnest anecdote and has nothing to do with Nice Guy Syndrome, but it’s worth mentioning because it shows what a loser I was.

Before Jinny, the one date I went on was senior year of high school. It was a lunch date. As in, it happened during school lunch time and I drove us to a nearby Teriyaki place and that was our date. Most people wouldn’t count that, but I do because... I mean, look at past Drew. He's so pathetic. He needs this.

Things didn’t work out. I could launch into a whole story and really explain the agonies of my thought processes, talk about how my asking her out was actually cute and funny and charming (can you believe it?), but I don’t need to.

All I’m going to say is: she was Mormon.

Yeah, of course it didn’t work out.

Public Pressure

Junior year of high school, I had a crush on Silvia and was like, “I'm going to ask her to Homecoming,” because that is what you do in high school when you have a crush on someone and are too big of a wimp to ask them out on an actual date.

I decided I wanted to make a big impression. I wore my three piece suit, purchased a rose - not a red one, come on, I wasn’t that tacky and desperate - and in front of all the sleep-deprived teens who populated study hall before school started, asked Silvia to the dance.

She said “yes.”

For the first time in my life, I had an unambiguous answer to the question, “Does she like me?” - “Yes she does.” Or so it seemed.

Asking her out in front of a bunch of people was a shitty move, the obvious reason being: when you do something like this in public, it puts so much pressure on the other person to answer in the affirmative, they are effectively forced to give the answer you want. Most people succumb to the pressure in that situation. Hell, if I get stopped by one of those Salvation Army bell people around Christmas time, the pressure gets to me so badly when there's only like three other people around that my desire to be seen as a good person is so strong that I usually end up donating a couple of bucks.

But also: I'm a sucker.

Not a lot of people are going to give a rejection in public to a dapper looking guy with a flower who is just so adorably bashful. Especially not for a Homecoming dance which is such a trivial thing that it really doesn't matter if you say yes, then renege on it.

Which is what Silvia did, by the way. I do not blame her for reneging. This was a lesson in, “hey - don't do this shit in public unless you're a hundred percent sure this is something the other person wants.”

The day and a half in between her saying “yes” and reneging though... my spirits floated at ozone elevations.

You have to understand that even though this was just a dance, every single remotely romantic advance I’d made in my life up until that point had been rejected. This was a much-needed win in my eyes. I used to make posts on Facebook that were simply fractions like, “0/4” or “1/7” with no other text to explain what I meant. Now, years later for all those people who saw those statuses and were so intrigued by the mystery and who definitely exist in the real world - what I meant, in the most pathetic secret code, was this: the number on the right of the slash indicated how many girls I had asked out in my life, and the number on the left was how many times it had been successful.

I used fractions to cryptically express my loneliness. Let that sink in for a second. Typical “nice guy” mentality, breaking relationships down into a numbers game.

Win for me or no, I don't blame Silvia for going back on it. I asked her to the dance in public and that was a shitty, coercive move. I didn’t realize it was shitty until someone explained it to me a couple days later. In retrospect, the shittiness seems obvious, but there’s the ol’ standby rom-com scene which is seared into our cultural memories: guy makes public declaration of love, she accepts, the gathered crowd applauds. Movie moments don’t translate well to reality.

I do blame her a little for the way she went back on it.

A day after she said yes and I had already done a bunch of fantasizing about how we were going to get married one day, she pulled me aside between classes and told me, “Hey, I think you’re real sweet, but my mom doesn't want me going with anyone to the dance. Sorry.”

“Oh no, really?”

“Yeah. Are you okay?”

“Yeah. I’m fine. Just sucks though.”

“I’m sorry. Hug it out?”


And then she gave me a pity hug.

All things considered, I took that well. I think I only moped for two days rather than a month.

But see what she said there? Her mom didn't want her going with anyone. For me, the answer to the question, “Does she like me?” was still trending in a yesward direction.

I, being a Good Sleuthy Boi, found her mother’s email address and was about to shoot an email her way. I happened to know where her mother worked and we'd talked to each other and she liked me, thank you very much, it wasn’t that weird that I found her email (OH GOD IT WAS WEIRD, WASN’T IT?! JUST LIKE THE SEX-ED STARING, OH GOD OH GOD OH GOD OH-). I wrote a first draft, then deleted the email - look at me, learning from my mistakes! I didn’t go through with it partly because my own mother was able to convince me that the whole mom angle Silvia presented me with was bullshit, and transparent bullshit at that. Yeah, I should have been able to figure that one out for myself, but recall: Drew is naive, Drew is bad at reading people, Drew wants to hope that he has a chance. I also didn’t do it because I realized that emailing the mother of a girl I liked but whose own feelings were inscrutable towards me would be something that only a manically desperate person would do. I was desperate, but like… not that desperate.

Anyway, I was annoyed that I was lied to and more annoyed that I bought it. A couple years later, Silvia would confirm that this was the case to me. While dropping that scintillating detail, she also clarified that her reason for turning me down was because at that time, I frequently wore fedoras.

I'm really not sure how to feel about that. My emotions oscillate back in forth between “how dare you” and “yeah, fair enough.”

I stan basic human decency.

I stan basic human decency.

Someone with a more acute case of Nice Guy Syndrome might have latched harder onto the “how dare you” feeling. “Why doesn’t she like me?” “Women are shallow.” I didn’t latch onto that feeling, so I think a nice round of applause is in order for basic human decency - let’s give it up for basic human decency!

A Witness to the Slaughter

Let’s ratchet things up a bit.

Junior year I'd fallen for theatre girl. Wait, theatre kids who spend all of their time in close proximity develop feelings for each other? Whom’stsoever heard of such nonsense?!

There was this conference our drama department used to go to every year called Washington State Thespians, which was a bunch of high school drama departments from all over Washington state meeting up for a weekend at either Central or Western Washington University. Workshops and mingling and trespassing and performances and general goofing-off abounded.

I'd had a crush on Winona for some time and decided that Thespians would be the perfect place to ask her on a date. Chances were, we would be able to be alone at some point and I could launch into my suave opening lines that I spent far too much time thinking about as I tried to go to sleep.

With patience, the opportunity to ask Winona out did present itself. Sort of. But I didn’t think a better chance was in the queue, so I went for it. It was a pretty bad opportunity, but fuck it, I’d spent too much time in my life waiting for perfect moments that would never come.

The two of us wound up being alone on a side path of Western Washington University. Just the two of us. Alone. Except - and this was the glaring flaw in the diamond of opportunity - not to far from us was Steve, another drama kid. He was just kind of… lingering.

I decided that it didn't matter Steve was there. I asked Winona on a date in front of him.

Steve choked on spit.

Artist’s rendering of Steve

Artist’s rendering of Steve

Winona and I pretended he wasn’t there. As far as uncomfortable moments in Steve’s life go, I’d bet this ranks pretty high. So much sympathetic humiliation combined with the feeling of being a third wheel without actually being a third wheel.

Winona turned me down.

This should have been where the Winona story ended.

With her turn-down, she left me the tiniest bit of ambiguity that she wasn't interested now, but could maybe, possibly, if cosmic rays were to strike her brain at the right angle and velocity, be interested later. I seized onto this tiny sliver of hope. “Does she like me?” - “A little bit!”

That thought parasite of “she’s playing hard to get” hijacked my analytical facilities. Given all the trouble it caused me, I really should have cleansed myself of that particular thought parasite after Nadia, but no, I would have to learn the same lesson ad nauseam.

The idea of "playing hard to get" is harmful bunkum.

I'm sure some people do “play hard to get.” The trouble comes when it’s one of your first assumptions in the analysis of a romantic situation.

Here's a tip: if you find yourself having that thought, discard it and move on to someone else. Whether they’re “playing hard to get” or not, it is not worth the effort. The person who plays games like that before a relationship is likely to play them during. But they're probably not actually “playing hard to get” and you've just told yourself they are in order to cling to hope.

You're better off assuming that there is no hope and moving on.

The current Drew can say this in retrospect even though it would take many many iterations of past Drews to learn this lesson.

I texted Winona often, trying to finagle a time when she was available. Maybe we could have coffee or something. Didn't have to be a big romantic thing, I insisted, even though I totally wanted it to be a big romantic thing. Motive-smothering - Nice Guy behavior, look out.

She was a chorus member in a teenage production of Pride and Prejudice… the musical version. I actually quite like Pride and Prejudice. I think Jane Austen is a fun and perceptive storyteller, but a musical version performed by teens is… it is sure a something to sit through. I made the dumb decision of seeing it alone. The whole time I watched the the production I couldn’t shake the thought that seeing a musical just to show a girl I liked support, and doing so alone, was total creep behavior.

I waited around after the show to say “hey.” I will never forget the look on Winona's face when she saw me.

I said: “Hey, Winona! Great job!”

She said: “Drew! You came!”

Artist’s rendering of how Winona reacted to seeing me

Artist’s rendering of how Winona reacted to seeing me

Her face said: "Oh god, you actually came."

We exchanged a few quick words before she retreated into the green room.

Even I felt weirded out by me. I called my efforts re: Winona quits shortly thereafter. I just felt gross about it.

Winona didn't do theatre at our high school during my senior year. I'm pretty sure it was due to circumstances that had nothing to do with me, but I am a neurotic and self-centered person, so I can't repress this niggling doubt that maybe she just really, really didn't want to be around me. I was senior leader. There could have been an unsavory dynamic had she stayed, but I had cooled off and I think we were on chill terms by the end of my junior year, but hey - neurotic and self-centered: I AM THE CAUSE OF YOUR PROBLEMS I AM A BAD PERSON. We get to the question of “Why doesn’t she like me?” My answer was “I’m a creep.”

How to Dance a Friend Away

Sophomore year, I had a crush on a friend of mine, Jasmine. We'd both done a lot of theatre together in high school. Biggest shock, I know, I'll give you a few seconds to collect your jaw from the floor and sew it back on. We had a lot of fun together. She made me laugh, I made her laugh, we talked shit about dumbasses - we had good times.

I didn't have a date to my sophomore year homecoming, as was my involuntary annual tradition, but I still went to the dance with a bunch of friends because I am easy to peer pressure. Jasmine’s date was a good friend nerdy of mine, Michael, who I occasionally played Xbox with.

The whole night I lingered around Jasmine. I thought that Michael wasn't all that interested in her. They were just going to the dance together, they weren't really dating or anything. “Does she like me?” “Yeah, probably, maybe.”

I lingered near Jasmine in the dance circle, building up my courage all the while. Visions of a confident, Charlton Hestonesque maneuver appeared before me: take her by the hand… and dance. Suave, confident… irresistible. When her and Michael danced, little bricks of jealousy were lain in the foundations of my confidence. She was so free. Taken by the music, her arms and dress flowed and her face was as bright as the mood-ruining hallway lights near the auditorium. She twirled in my direction - not at me, merely towards. I took it as the Gods of Homecoming Dance giving me permission to make my Charlton Hestonesque visions into reality.

I reached out and squeezed Jasmine’s hand.

She jerked her hand out of mine with a verbal “NOPE” and spun away.

Sheepish and feeling the prickles of the nerves inside my skin, I continued to shimmy as though nothing had happened.

Michael saw it all. I did my Charlton Loseresque move right in front of him. HE WAS LITERALLY RIGHT THERE. DREW, WHAT THE FUCK WAS THAT ABOUT? DREW, WHAT THE ACTUAL FUCK WERE YOU THINKING?

Michael stopped being friends with me.

Truth is, I didn’t realize he was mad at me until years later.

Jasmine was definitely pissed off about it. I can just picture her with Michael after the dance saying, “What the fuck was that about? How dare he!” She was the sort that held a grudge, but I guess I had juuuust enough friendship goodwill built up that she forgave my transgressions within a week and I was none the wiser that I had goofed as badly as I did.

See, there’s an upside to men being socialized into aggressively pursuing their mates: it means that when they overstep their boundaries, it’s easier to write off as “that’s just the way boys are.”

Yayyyyyyy I’m a beneficiary of socially-prevalent unconscious biases and I hadn’t realized it until my early twenties yaaaaaayyyyyyyyy.


In eighth grade, I was a part of a program through my hippy dippy new age church called Coming of Age. CoA was a dozen or so middle schoolers in Seattle meeting at said hippy dippy new age church on Saturday mornings and going through a… coming… of… age.

The idea behind the program was to provide guidance to teens during their transition into adulthood. It is a common touchstone in the majority of world cultures to have some sort of ritual based around that transition. Modern America does have some rites of passage that could be considered “coming of age,” but most of the ones that come to mind are not healthy or spiritually fulfilling. Losing your virginity can be considered a coming of age moment, for instance, or smoking pot for the first time. Of course the american coming of age isn’t necessarily negative - first job and graduation also count. But there isn't a spiritual edge to any of these, nothing that helps you reflect on who you want to be as a person. I mean, sex and marijuana can be spiritual, but as an idiot teenager? They’re probably not.



Under the guidance of some Cool Adults, we went through various coming of age rituals, minus the extreme torment that tends to go along with them. Did you know the Kalenjin of Kenya have an initiation ritual involving wide-awake circumcision and if you show pain, you’re ostracized? Yeah, that shit wasn’t gonna fly.

Nadia was a part of Coming of Age. Within the first month, I fell for her harder than a piano on Wile E. Coyote. As in, when I talked about her to my friends I used the "love" word. So dizzying were my feelings, I thought that this was what soulmates were and I would never be in love with anyone else ever again.

I always wanted to tell her how I felt during Coming of Age Saturdays, but I didn’t have the courage/we were never alone. Nadia was the only reason I looked forward to those meetings. Imagine my heartbreak when one Saturday, she wasn’t there. I asked the woman in charge and she told me that she dropped out. It was only a couple months before the program was over.

But we’re meant to be together, eighth grade Drew thought,That can’t be the last I see of her. I started insisting to my parents I come along to the regular church services, neglecting to mention I only wanted to do so because I hoped Nadia’d be there. Most of the time, she wasn’t. I did end up seeing her at church twice. What I remember most about these is that we were really hitting it off, banter between us was good, and the entire time I was aching to let her know how I felt, but there was never a moment when we were alone enough for it to work out.

She lived about an hour away from me. I ignored anyone who told me this non-relationship was doomed. I was crazy for her through the entirety of both eighth and ninth grade.

How crazy was I? One of the first things I did when I made my Facebook account was list my relationship status as "it's complicated." Because I was "taken” and not looking for anyone else. It's just that I hadn't told her how I felt yet.


Not long after Coming of Age ended, I called her home phone. I left a voicemail explaining that I was trying to find out the emails of the people I wanted to stay in touch with from Coming of Age and that Nadia was one of them, so here’s my email. This was a lie. Given what a terrible liar I am, I'm shocked that I didn't have a seizure and bite my blaspheming tongue off as soon as the words left my lips.

But it worked. She emailed me. Now that I had her email, I could talk with her directly without worrying about pesky parents. She didn't have a Facebook and I wasn't about to ask for her cell phone number because that would be crossing the creepo line. Leaving a voicemail asking for her email that her entire family had the potential to hear somehow wasn’t.

But I couldn’t strike up an email conversation just for the hell of it, could I? No, I needed to have a pretext, some delicious plausible deniability so she wouldn’t suspect me of being flirtatious. I started plotting my best course of action and got annoyed with myself very quickly. I'm smart, goddammit - I get straight A’s! There's got to be something I can come up with that will work… I thought, pacing around my cousins’ basement. I recused myself from all family events on that visit so I could figure out the perfect way to get her to be my girlfriend, as though this were a game of Sudoku and I needed to hop on the right thread of the puzzle’s logic, inevitably bringing me to the correct answer. I came up with scheme after scheme, generating oodles of harebrained plots that I deluded myself into believing were clever and coy. Obviously, I was a boy whose mental frameworks in no way needed readjusting, because I fell upon this completely normal solution: I started an "email list" where I would happen to dole out random life updates to Nadia and the other friends whose emails I had. Exactly the plausible deniability I was looking for. I congratulated myself on my ingenuity.

To both of the Jareds who received several inane emails over this time period - sorry for that. Now you know why.

Whenever I sent an email, I refreshed Outlook every fifteen seconds to see if she'd replied.

Nadia and I had a few good emails back and forth. Nothing that an outside observer would sanctify as ~tHe rElAtiOnsHiP oF tHe CeNturY~, but it was friendly, she was funny, I was funny, we revealed more about ourselves to each other - it was good. I even confided in her how my Driver’s Ed class played us a gory video called Red Concrete on the dangers of drunk driving and it really disturbed me.

Come the summer between Freshman and Sophomore year, I couldn't take it anymore. My feelings were eating me up inside. It was killing me. It was another cliche for holding onto potent feelings and needing to do something about them.

I mean, we were good together, right? Like, she definitely enjoyed being around me, right? By that summer she had a Facebook, so we were chatting a bit on there too, and that was great, that was like... whoah, we are basically already dating, right? I mean, I analyzed every Facebook post of hers and concluded that, while she would never outright state her feelings for me, they were totally there. I hung on each post, looking for clues, sighing as I imagined us holding hands, walking down the street, eating lunch in a cafe (wait, was I fantasizing what people think Paris is like?). I felt such intense love, so much love that… what if soulmates were real? No that can't... but what if? I mean, she's got to love me too, right? I mean, she's a quietish person, she's probably just scared. “Does she like me?” “Well, we’re soulmates, so yes, but she’s too shy to bring it up.”

I made up my mind to ask her out. She was going to say yes. There was no way she wasn't. We were meant to be together. Screw living an hour apart on a good traffic day, we would make it work… because love.

One summer afternoon when I was home alone, I called Nadia’s home phone.

No one picked up.

I waited a month while I recovered from my heart attack.

I called again, again waiting until I was home alone.

Again, no one picked up.

I called again, home alone once more.

Her mom answered.


"Hello, this is Drew, could I speak to Nadia please?”


“Oh, uh, from Coming of Age. Nadia’s friend. I’m the one who, uh, was asking for emails to, uh, stay in touch.”

"Okay. Sure, give me one second."


The wait for Nadia to come to the phone was interminable. My knees were getting weak and head getting light from not breathing, so I curled up on the sofa, shivering and clutching the phone the way a heroin addict would cradle the last dose in their stash.

Finally, Nadia: “Hello?”

“Hi. It’s Drew,” my throat was dry, I was hot all over my body and the summer heat was not to blame. My eyes were wide with terror, more like if were encountering a ghost than doing what I was going to. Prolonging my torment, I stalled with small-talk. I asked her about the skiing vacation she just went on and the like, but the whole time my voice was on automatic and I wasn’t listening to her. I was too focused on what I was about about to say. Come on. Just say it. Spit it out, coward.

There was a brief lull in the conversation. It was time. Now. Do it now, you coward, do it now! I delivered the epic line I spent months of sleepless nights working on: "Um... I was just calling because I wanted to ask if you would be interested in going out with me."

Fucking perfect. Knocked it out of the park. I was a flop-sweaty, trembley mess, but my voice was perfect and confident and there was no way she would say -

"No thank you."

"Oh. Okay. That's all. Um, goodbye then."


And I hung up.

I burrowed into the couch. When my mom got home, she asked if I was okay. I said I was and she didn't press more than that. The next several days, I was a depressed mess. I moped like only a true Eeyore can. I started liking a bunch of pages on Facebook that were things like, “i may look alive, but i’m dead inside.”

This is where the Nadia story should’ve ended

But it didn’t. Because then I did some really, really stupid shit. Stupider my “I’m such a cleverboi” email list scheme, stupider than snagging Jasmine’s hand in front of her date.

Not long after the phone call, I began to message her frequently on Facebook. "Hey, I'm sorry, but maybe there's a chance we could talk this out?" stuff along that vein. I do not remember what I said in those messages. I've repressed that memory and I actually attempted to go back far enough in Facebook Messenger to see what I said, but unfortunately/fortunately, it doesn’t have any conversations saved from before 2011. Oh no. But there were a lot of messages. Whenever her "online" blip was green, I shot her a message, just a definitely casual "Hey!" in the hopes that we could simply chat. My hope was that if we could just get to talking more, she'd come around.

Recall that “hard to get” is harmful bunkum.

“True love” and “soulmates” are also harmful bunkum.

Love is real. Being consumed with thoughts of “true love,” however, is only going to lead to disappointment when you wonder where the hell your promised soulmate is. Even worse is when you’ve decided that someone is your true love. Nothing they do can shake that conviction. Every “I don’t want to date you” becomes just one more barrier between you and your soulmate. You’ll just have to try harder to get together.

“Does she like me?” “Yes. But she’s in denial.”

I thought she was playing "hard to get." I thought we were destined for each other. What a poisonous combination.

Guys, I sent Nadia so many freaking messages.

How is a girl to respond to a guy who won’t get the fucking hint? There was a human being on the other end of my messages. I wasn’t thinking of her as one, I was thinking of her as “future girlfriend,” which is typical Nice Guy behavior. At the time, I couldn’t imagine how uncomfortable or anxious I must have been making her - but I can now. This Drew kid wouldn’t take “no” for an answer. Every time Nadia logged onto Facebook, there would be a new message and it must have been an immediate pulse of anxiety. I don’t want to put words and feelings in her mouth, but how could she not have been uncomfortable? And frustrated? And anxious? Maybe afraid, maybe angry. How is a girl supposed to respond to a guy who won’t get the fucking hint?

One day, I logged onto Facebook and found out that she'd unfriended me.

The story should've stopped here

Finally, the question changes from “Does she like me?” to “Why doesn’t she like me?”

My answer was: “I’m a total creep. Oh god, she hates me. I have to change her mind.”

Soaring into a fevered panic the moment I noticed the unfriending, I sent a flurry of desperate messages. I protested, saying that I was sorry for being so pushy, that I would stop, that I just liked her and she was great and we could be friends, I’d be fine with that. Please, just let us be friends, I'm really sorry for all the messages, I'll stop doing that, really truly I promise, just please talk with me, please be friends with me, please!

I couldn’t comprehend that things could never go back to the way they were before. Not just because of my incessant messaging, but because now that I’d let on to my true intentions with the phone call, everything that came before would now be run through a filter of that knowledge - that I was only being nice and friendly because I hoped we would date, and it never was about making friends or “just keeping in touch.”

I actually do remember one of the messages I sent during this time period. It was this: “Okay, I get the message: ‘shut up, Drew.’ I’m sorry. I won’t do that anymore. I promise. Let’s start over. Let’s pretend like this didn’t happen. I’ll be good. I promise.”

Nadia never responded and never re-accepted my friend request. How is a girl supposed to respond to a guy who won’t get the fucking hint?

Best response she could have made.

Even though I was convinced it would never happen, I did get over Nadia. Once the mad conductor in my mind who guided my actions finally choked and died on his own conductor’s wand, I felt sublimely foolish over what I’d done.

I know that in the grand scheme of things, what I did to Nadia was far from the worst behavior, but it leaves me deeply ashamed every time I think about it. When I was in London for a school trip, the memories of all this came flooding back to me so very vividly. I felt so guilty, I wanted to re-find her on Facebook and tell her how sorry I was, but thankfully, my brain was successfully working and that didn't happen.

This was a pivotal event in my life. It made me even more apprehensive to ask girls out than I already was. I fell into a defeatist mentality - “It doesn’t matter how much I like someone, they’ll turn me down.” But as you can see from the stories that came after, it only cemented some of my bad habits. I still overstepped boundaries.

If I did learn anything, it was this: don’t make friends with someone with the sole intention of turning it into relationship. More often than not, the girls I fell for I was already friends with and my feelings just changed at some point. Is that better? I don’t know.

I wonder if Nadia remembers this. Nadia - that's not your real name, but if for some reason you're reading this, you know who you are - I want you to know that over ten years later I still feel a deep sense of shame over what I did. And I am very sorry.

Stories are Done - Let’s Conclude

I’m willing to bet a lot of people got to the end of this and went: “Really? That’s the worst you’ve done? That’s what you’re doing a whole confessional about? Where’s the cheating? Where’s getting pepper sprayed? Or sloppy inebriated sex? Come on, lame!”

To which I say - well, point for you. I don’t lead a very exciting life. But just because these stories are tame in comparison to some of the lurid stuff we read in the news doesn’t mean there isn’t anything instructive. It doesn’t make my shame go away, though I am a very easy person to shame.

I have always been a bad hopeless romantic. I'm not very suave, confident, or charming. If “reading people” were on the SATs, it would have dragged down my score severely. I have a tendency to stick to my own pre-thought-out script rather than improvise.

As evidenced in these stories, I had Nice Guy Syndrome. If I was just nice enough, she - any of the shes - would see that no, she did, in fact, actually want to date me. A lot of my actions were based around convincing someone that we would be good together. With Silvia, I stopped short of emailing her mother; with Winona I was trying to show how supportive I was by going to Pride and Prejudice: the Musical, not to mention all those text messages prodding her to give me a chance; with Nadia… well.

It's not a good mindset.

To pretend like it ended with these stories, however, would be a lie.

I wanted to tell these stories for a few reasons. I felt like, for once, my own personal experience allowed me to have a perspective on a relevant social issue. I also believe it's crucial as a ~crEAtiVe pErsON~ to investigate painful places. Art lives in the sore, infected, picked-off scab. It's about taking an honest look at who I am as a person and asking: am I different? Have I really changed as much as I think I have?

I have changed. Although in order to prove that, I would need to become single again and run some scientific tests, but that’s not going to happen anytime soon.

Looking at all of these various romantic threads, some connective elements stand out to me. Fear of rejection. Hearing what I wanted to hear. Willfully latching onto a look or a phrase just so I could keep the hope of a relationship alive. Lessons taking a very long time to be learned. That I am not guiltless when it comes to pressuring others.

At the same time, all relationships are messy because people are messy. No one is good at relationships and dating the first several tries. Which isn’t to excuse shitty behavior, but to acknowledge that everyone is complicated and makes mistakes.

#metoo is exposing the bad practices of powerful men. Powerful men get away with so, so freaking much in this country - world - and it is satisfying to finally see comeuppance for past misdeeds. But “boys will be boys” has been applied to more men than those of Kavanaugh’s stature. There is only so much leeway that can be given to a boy’s behavior when we say, “relationships are complicated.” Everyone draws their own line as to when the behavior goes from “innocent bumbling” to “a problem.” I don’t know where I draw my line because relationships are complicated and the socialization of boys and men influences behavior, even during "innocent bumbling.”

My mistakes can often both be cast as naivete alongside corrosive socialization. These are not mutually exclusive. Both are true, and neither is an excuse.

Going forward, I think it’s best to approach such topics with honesty. I am imperfect and denying fuckups is part of the problem. If a “nice guy” refuses to have a reckoning with the past things he’s done, is not willing to recognize that he has been a bad person, and that it is okay to have been a bad person because you can choose to be better than you were before, then that “nice guy” is trapped in a self-reinforcing victimhood where women always fall for assholes and feminism means the enslavement of men like him.

The “nice guy” mantle sucks for so many reasons which this overlong article has attempted to critique, but one I want to leave you all with is this: the “nice guy” mindset is disingenuous. It is a story told to the self and others in which wrongdoings and nuance are drowned. If you claim to be a “nice guy,” you are not only robbing women of their humanity, but you of yours for refusing to reflect and think, “I did a bad thing.”

Be honest, be kind.

Drew, out.

Five Years of Being So Cute It's Gross

The Meaning of Life