To All the Boys I’ve Loved Before (PART I)

When I was 13 one of my biggest fears was the pain women go through with childbirth. I used to think about it a lot.


But I’d be sitting in the back of the car (because my mother refused to let me sit in the front seat until I was in high school; yes it was as humiliating as it sounds) and get REALLY stressed out about the pain I’d have to go through one day. I found solace in the knowledge that was still like, 10 years away…

LOL yes, that means that I thought I would be having children at AGE 23. Part of me is like oh that’s cute and part of me is like hmm wish I could tell 13-year-old Ails that she could double the 10 years to 20 years…

Because here am I, 26 years old, and single. As. Fuck. Not even someone to drunk text. Like I’m so single my brain keeps giving me dreams about getting back together with various ex’s/fuckboys just to remind me that HEY YOUR BIOLOGICAL CLOCK IS GOING TO START TICKING AND ALSO I AM LONELY AS FUUUUUCK.

My friend was joking with me last weekend after I told her that I quit my job and was going home for a couple of months — “you know this means you’re going to meet the love of your life right? And it’s going to fuck everything up?” Yeah, no, that would be totally on brand with my life right now.

PSA: Dear hot Scottish men who may see me across the room in the bar during the Ireland/Scotland rugby match this weekend — DONT TALK TO ME. IM NOT READY FOR YOU.

Christ. At least it’s acceptable up here to not be married at 26, ya know? Cause I’ve hit the age where my friends from high school at home have started having babies on purpose. Still trying to wrap my head around that one.

But up in NYC, it’s just not a thing till you’re in your 30s now. No one cares. Casual dating? Okay fine, maybe a little. But Tinder still rules the kingdom.

Which has gotten me to ~thinking~ back to some of my past “escapades” with men (LOL boys) in my life? Starting with my very first crush…..

Dad, you should stop reading now. 


CORY, 9 years old

Cory was a boy 2/3 years older than me that sang in the junior choir at church with me. I’m 100% he never knew my name and would NEVER remember me now. He was only there because his dad was in the “senior choir” and forced him to do it. You could tell he was not amused. But I didn’t care because I was obsessed. I’d sneak glances whenever I could and would be devastated on weeks when he wasn’t at practice.

I harbored this secret because I couldn’t bare any of my friends to know and tease me about it. Though he was a perfectly respectable first crush subject. Dark brown hair, blue eyes, you could tell he was going to be tall but not too tall — which LOL is still my type 15 years later.

Corey eventually stopped coming to choir and I never saw him again. It was a sad day for 9-year-old Ailsa.

However, I did come across him on bumble one time while I was home for Christmas and turns out he has a really questionable beard now, so it’s all good.

After the Cory fiasco (why am I calling it a fiasco? Literally nothing happened), all was silent on the crush front for several years. All the girls in my class started “going out” with the little douchelords that made up the male population of our grade, and I was like fuck this. I got asked out by a couple of guys that I was so not interested I and was so mortified that instead of politely declining, I cried, then gave a bitchy WHY WOULD I EVER GO OUT WITH YOU?! Response. I think I may have called one a freak. He was not. He was (at that point) a seemingly fine dude. Not my best moment. I probably scared those poor boys for life.

There would be the occasionally forced crush that I felt like needed to happen, but overall I was over those fuckwads.


UNTIL: MICHAEL, 11 years old

I came across Michael when I joined my dance studio. Yes — I know what you’re thinking — and yes, he is gay. But we were 11 years old and at that point in his life, he liked el chicas.

Problem was every other girl at the dance studio ALSO had a massive crush on him. So what do I do? Pretend to be the only one not interested. I would be cordial to him when we spoke, but other than that, pretty much ignored him. I’ve never been interested in things that everyone else wants. Well, at least outwardly ;).

Michael was cast as Prince Charming in the production of Cinderella we were putting on that year, and starting “going out” with the girl playing Cindy. It was pretty clear to everyone at the studio that this was some intense puppy love shit, so everyone kind of backed down. This was around the time I realized he was gay, though no one believed me. The crush faded pretty quickly at the point. But he and Cindy went on to date for like 6 years and were cute and whatever and then he came out in college. I still like to be the one to say, “I TOLD YOU SO.”

So middle school comes and goes without much on the boy front beside a year of secretly pining away after someone who liked boys, an awkward slow dance at the school dances, and being fun of for wearing a Limited Too training bra. Eek.

And then it was time to enter HIGH SCHOOOOOOOOL!!!!!! High school was a weird time for me. I was not about it. I started off at this little hell hole of a school that I did NOT want to go to, and then ended up transferring my sophomore year to a preppy-ass college prep school. Shall I say prep one more time?

My mom and I used to refer to my first high school as “The Land of Misfit Toys.” It was full of art geeks, stoners, emo kids, literary savants, and pretty much everyone who would be sitting at the “weird” table in the cafeteria scene in a high school movie. Shit I hated that place.

So the first boy who becomes interested in me is the sophomore named NATE (14 years old).


Nate was a grade A emo kid. Honestly, I have no idea why he decided that he was going to go after me — I was a geeky little 5′ tall girl with the body of a 12-year-old boy who had a hankering for bizarre graphic tees from Delia’s. But for some reason Nate decided I was cute. And OK I guess I was like a 32A at the time. But he decides he likes me and begins the whole AIM courting process. And I’m too petrified to really do anything about it but be nice. And somehow end up agreeing to go out with him even though I really didn’t want to, but didn’t want to be mean. GOD WHAT WAS WRONG WITH THE WORLD WHERE WE TAUGHT GIRLS THEY CAN’T SAY NO TO A GUY WHO ASKS THEM OUT?!?! So I agree to “go out” with him. AND NO — we literally never hung out except for when I saw him at school which was pretty much be just avoiding him in the hallways and being super awkward at lunch. OMG I remember one time sitting in the computer lab and he walked by and dropped a sticky note on my keyboard that said “te amo.” Like Jesus, I still get so uncomfy when I think of that. I vaguely remember my friends being like, Ailsa, you are obviously wildly uncomfortable and not remotely interested in this boy, you need to break up with him. So I called him on my flip phone on the sidewalk outside of a sushi restaurant in the Highlands (a cool neighborhood in my hometown) and gave my very first “it’s not you, it’s me” talk. Oh god, it was horrible. BUT I WAS FREE! To keep avoiding him in the hallways…

I swore off boys for the remainder of high school after that. JK. About 3 months later I met Jake.


JAKE, 14 years old

I had my first kiss when I was 14 in a movie theater during Pirates of the Carribean: At World’s End. If that’s not romance kids, then I don’t know what is.

Jake and I were star-crossed lovers. We went to rival schools, he had just broken up with this girl who I was “semi” friends with, and we were just soooo not allowed to be together. Which for a 14-year-old makes it SO MUCH MORE EXCITING!

But we were never fated to last…

I had my first kiss at 14 but I also had my first heartbreak. I don’t remember how we got introduced, but I know that we hit it off immediately. It was late March or so and he had just broken up with this girl Rachel whom he had dated for 7 months. Which, at 14, seemed like an ETERNITY. Actually now that I’m thinking about it, I think it was actually Rachel who introduced us in an effort for me to help them get back together. Wow I am HORRIBLE person.

Jake and I get on swimmingly and start to develop the feels for each other. The Island of Misfit toys only had one dance a year, The Prom, and every class was invited to attend. I brought Jake as my date, despite Rachel’s and her friends’ protests. Omg I am seriously such a witch. But I really liked him!!!! And I had never had a boyfriend!! Or a date!! THIS WAS IT!!!!!!!

Prom took place after the last day of school. A great time was had by all. We didn’t kiss that night, but I wasn’t discouraged. Also not really sure if I was ready to be kissed at that point, but I KNEW IT WAS COMING!

Jake and I proceeded to spend almost every day together in the weeks following prom. It was summer, our friend groups got along perfectly, and no longer had to deal with Rachel and her annoying friends hounding us.

Jake and his friends and I spent the early days of summer riding bikes through the highlands, hanging out in parks, and eating ice cream in each other’s backyards.

The infamous movie night was planned, and I knew it was going to happen.

2 hours later, the deed was done, and WOW was I excited. I had been kissed!!! I was a woman!!! LOL. I was cute.

We went on hanging out for the next week or so until I decided it was time for The Talk. Dun dun dunnnnnnnn. You know — the “what are we talk.” I wanted him to be my boyfriend, and I was pretty sure we were on the same page. Welp. Turns out I was very wrong.

Jake, as it happens, wasn’t interested in committing to another relationship so soon after the Rachel Debacle. And I was dumbfounded. I did not understand. In my mind, it was over. I didn’t see the point in continuing on if he didn’t want to be my boyfriend. And so the Jake chapter was over almost as fast as it began.

Aww poor little broken hearted Ailsa. I remember laying in my bed the next morning not wanting to get out up. My mom came down to my room and took one look at me and say, “He ended it didn’t he?” I don’t know who was more upset. Me, or Mom.


EC, 15 years old

As I mentioned, sophomore year I transferred to another school. I knew no one there and hadn’t even visited before starting that fall. Immediately, I was the cool mysterious new girl. And Oh! I had gotten boobs at this point! So I was basically invincible.

Pretty quickly into the year, it’s brought to my attention that a boy in my class, whom we shall call EC, likes me. I’m like, ok I’ve legit never talked to this kid nor do I have any classes with him, but HEY HE’S CUTE AND HE’s POPULAR LEGGO!!!!

So then we start talking on AIM and one thing leads to another and he asks me to Homecoming. Hoooooooooly moly was I psyched. I was going to homecoming with a cute & popular boy who liked me and I was PROBABLY going to be kissed again and awwwwww shit did I think I was hot stuff.

I feel like I should stop and take a minute to discuss my relationship with EC. He was never my boyfriend though I sometimes just refer to him as the Highschool BF to avoid a  long explanation. It’s just easier. To this day, I have a lot of complicated feelings about him, and sometimes don’t know what to make of them all. He did some really terrible things, but I don’t think he’s a terrible person. He’s still someone who’s in my life, and in the past year or so has become a good friend again. But it took many years for me to even entertain that thought.

Anyhow, back to homecoming! I wore a black BCBG mini dress. We took photos before the dance and went to his house with a group of friends afterward. I don’t remember much of the dance itself, but I think I had a good time. At the end of the night, my Dad came to pick me up, and EC walked me upstairs (it was a basement gathering, duh). When we got afraid from the rest of the group, I thought he was going to lean in for the big schmakeroo BUT HE CHICKENED OUT! And obviously I chickened out too, so I don’t know what I’m getting all worked up about. After that, things started to die down a bit for EC and AH. END ROUND 1….


SAM, 15 years old

Sam was my first foray into Cougar Town. That’s right ladies and gents. SAM WAS A YOUNGER MAN. By a whole year, omg. This is a short enough saga. Sam and I met on the swim team in high school. A flirtation started, and all looked like it was on track for us to start going out. Then my friend Carly decided she wanted to hang out the night that I was supposed to hang out with Sam, and how was I supposed to know that blowing Sam off to chill with my best friend was supposed to signify that I was no longer interested?!?! Ah, young love.


EC, Round 2, 16/17 years old

Round two of EC gets rough. And that’s putting it lightly.

Sometime during the summer before senior year, EC and I ~rekindled the flame.~ We continued talking throughout the fall of that year, and I started to develop some pretty intense feelings for him. We kept truckin’ on as just friends, until early December when I decided to take a big risk and drop the L bomb on him.

Like, people, like. I told him I liked him. You know, as more than a friend.

And then, all hell broke loose.

The next nine months was a rollercoaster of shit. Of us hooking up, of us not speaking for weeks on end, of us deciding we were better as just friends, of me asking him to the Spring dance, of us realizing we couldn’t be just friends, and him going out to parties and me hearing the stories of him with other girls the following Monday…

Man I still get whiplash thinking about it all of these years later. Obviously, when I think back to it I think why oh why did I do this? Welp, it’s part of my story, and there’s nothing I can do to change it.

When I told him that I had feelings for him, he was very clear that he did not want to be in a relationship. We were getting ready to go off to college, and he didn’t want to get all tangled up dating someone when we would be leaving in just a few months. Fine, I understood that. I also understood that he was just the type of person at that point in his life that he wasn’t ready for the kinds of feelings or commitment that I was. I accepted that.

And at that point in my 17-year-old life, I thought that was enough for me. I didn’t think I needed the title of him being my boyfriend. And this sure as hell was better than just being friends.

The following Saturday night I found myself “watching a movie” in his basement (we were making out. I was making out with a boy I liked and it was weird and kinda gross and I was SUPER STOKED).

And then the next weekend he was a party sucking face with Liz Pascal.  And that’s when I realized that I wasn’t the ‘casual hookup’ kind of girl.

I told him that I was sorry, but I actually wasn’t down for the whole friends with benefits thing. I acknowledged that I wasn’t asking him for anything more and told him that we should go back to just being friends.

Easier said than done.

He seemed to be 100% fine with snapping back to our old ways and acted as if nothing had happened between us. Which was really hard for my little teenage heart to take. I got super bummed, and realized that continuing to take every day wasn’t going to do me any favors.

So, I decided to stop talking to him. For 2 months. Which is a pretty long time when you’re a senior in high school. I broke down the day before Valentine’s Day and texted him. I thought that enough time had passed and that I would be fine talking with him…lol.

Of course, within like 2 weeks I’m back in deep. We toyed around with the idea of going to the spring dance together, the one where girls ask the boys, as “friends” (*rolls eyes*). The theme was “Enchanted Sea,” which was PERFECT because his favorite animal was a manatee. While he was in lacrosse practice (he was captain of the lacrosse team, which I probably should have mentioned earlier because I feel like you now have a much better image of the size of douchemonger we’re dealing with here), my best friend and I printed out about 2 dozen cartoon manatees and taped them to trees/poles/fences/buildings all along the drive from school to his house. There was one final manatee on his front door that said, “Out of all the manatees in the enchanted sea, will you go to the dance with me?” Yes, I’m aware, I am a genius people.

We continued to insist that we were just going as friends. Which is laughable considering we were making out about 30 minutes into the after party.

The even more laughable thing? He proceeded to walk into another room at the party and suck face with another girl. HA. So funny, I know.

Cue a solid week of Taylor Swift lyrics as away messages and me ignoring his texts and when he tried to talk to me at school.

You don’t have to call anymore, I won’t pick up the phone…

At least he realized he fucked up this time and was showing some sign of remorse. He finally promised me that he’d leave me alone if I would just come over and talk to him one day after school. I remember thinking This should be good. And promising my best friend that I wouldn’t end up hooking up with him. He actually apologized. I was SHOCKED. Andddddd just like that, I had forgiven him.

What is this, like round 45 at this point? Christ. I hate myself. I keep wanting to just skip the end of the EC chapter, but THAT’S NOT WHAT I’M DOING HERE. Just keep typing, just keep typing… 

I actually was pretty good for the next six weeks. We somehow found a way to be friends without any extracurricular activities. We were able to hang out one on one and have a great time with no funny business. It was great! Until he got annoyed that I was going to prom with another guy in our class.

Our mutual friend Caroline got wind of what was going on, and decided that she was going to play Yente. She got me to admit one night after a few beers that yeah, I still did like him. But I said it just wasn’t meant to be. Of course, she starts texting him that I’m saying I still like him…to which he responds well yeah, I like her too… and, well, YOU KNOW THE STORY.

That summer was a complete and total shit show. I’m not going to go through all of it because I’m tired of embarrassing myself. It was bad decision after drunken argument after bad decision (many on his part — including sleeping with the aforementioned Caroline) that culminated in us not speaking for the last 6 weeks of the summer.

And that then found me living out “White Houses” by Vanessa Carlton after about four too many shots of cheap vodka at a house party.

There’s a little part of my heart that will always be broken over that.



I would like to take a moment to address that I no longer stress about pain from childbirth. I am going to be THE MOST DRUGGED UP. Give me alllll the epidurals. To all of the women who dream of having a natural birth: good for you. I am not one of you. And unlike what my college boyfriend once told me, NO, IT DOES NOT MAKE ME LESS OF A WOMAN TO WANT DRUGS!

“But I hold on to your secrets in white houses”

― VC


1 thought on “To All the Boys I’ve Loved Before (PART I)

  1. You are so funny and honest Some of your expressions just had me laughing out loud. The Lacrosse team thing, and expeditions into cougarville… just hilarious. That Caroline though… as soon as you said she tried to hook you back up it smelled fishy to me. A good friend would never tell a “friend” to go back to someone who’s “just not that into you.” (title of a 90’s book I think). You were kind and loving to him and he was not into it… sadly it sounds like he would never be into it until you’re no longer into him (so, null). The fact of Caroline ending up with him kind of proves she had ulterior motives… WOW I’m really getting into the intrigue here. Good writing. Just keep typing. :)) your blogging bud xoxo n (p.s. 4 natural births, one of them orgasmic… I was scared too, and lucky because I had an awesome midwife for three of them… but it’s not that bad. 😆)

    Liked by 1 person

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