How My High School Crush Turned Out As An Adult, 20 People Answer

Published 2 years ago

When Katy Perry’s song ‘the one that got away’ plays, who comes to your mind? If you’ve ever had a crush and wondered what they were up to these days, you’re not alone. As millions of people will concur it happens to all of us. But some folks have kept tabs on the crush from their youth and upon reflection share their thoughts on it in hindsight.

More info: Reddit 1 | Reddit 2 

Read more


Image source: sderou20, Artem Podrez

An insanely talented molecular biology researcher at Boston. And she’s still insanely attractive


Image source: thrashglam, Max Avans

He’s 32 and still works at the same pizza place and is a conspiracy theorist so I feel like I dodged a bullet.


Image source: DrRoborknik, RODNAE Productions

I had three. One from the first two years and two from the last two.

The first one is now F to M trans, who walked to Colorado to join a cult/commune. He is now in Arizona recording rap albums.

The second girl moved to Florida and lives in a swamp. She periodically hits me up to tell me she misses me, how dumb I was that I didn’t follow through, that we should get married.

The third was a missionary. She wasn’t really into it once she grew up, came back home and I introduced her to one of my closest friends. They’ve been married for 15 years.



Image source: BitwiseB, CoWomen

Began acting. It’s weird – every so often I’ll see a commercial or something and be like “oh, hey, I know them!”

My crush is an incredibly sweet person, so I’m glad.


Image source: dogchowtoastedcheese, Anna Shvets

Went on to be a teenaged model for hair products, graduated from Yale, toured Europe, opened her own successful ceramics company that is sold worldwide and is often written up in magazines. Makes me feel like s**t every time I think of her.


The guy I crushed on for 2 and a half years did not end up turning out great. I’m still friends with his younger sister, so I know that he recently acquired his third DUI and his second divorce. He’s currently living in his friend’s basement and occasionally works for his friend’s moving company as a mover, but only when he feels like it. He spends all his money on booze and owes the two moms of his 5 kids tons of child support. But man, was he hot in high school.

My second crush in high school is the only reason I got over my first crush. He’s currently doing great, mostly because he gets to be married to me for going on 20 years :D.

Image source: I_Want_A_Llama


Image source: gorgonheap, Anna Shvets

Still a ten for looks. I’m sure she kept on as the amazing, kind person she is. She moved to another country, speaks multiple languages and is more successful than I imagined. She seems happy but we haven’t talked since the time I told her how I felt about her about 20 years ago.


Image source: Gunslinger_11, RODNAE Productions

She worked with the Obama administration (I forgot in what capacity) got married to some politician’s son (don’t remember don’t care to look up.)

She is happy and that’s the only thing that matters, oh she was also our schools Valedictorian she was so busy with her job she could not organizeour high school reunion so that’s a plus.

I wasn’t head over heels for her I admired her but I knew I wasn’t for her.

Then there’s another crush of mine, we ran into each other years after graduation at grocery store. After talking I asked her out to dinner at my house, I pull out all the stops I buy rainbow trout filets and make all the fixings.

6:30 rolls around I open the door and “who the hell is this man behind her?” Oh this is my fiancé , she tells (neglected to tell me about) me. Turns out they wanted to sell me on some MLM thing. She tried to cross the threshold I put my arm out and asked them politely to leave. I turned away from the door and had my saddest meal I ever ate.


Image source: boltgun_to_the_face

Pretty good. Seems to have her life together, although she had a few setbacks. She’s gone back to uni since job prospects in here field kinda sucked, but seems to be really enjoying it.

She’s dating me though, so clearly her judgement sucks.


Image source: BobSacramanto, Elina Fairytale

Still super hot. She married some loser and has a few kids with him.

That loser was me. Just celebrated 22 years of marriage.


Back when I was younger and crushing hard I got on AOL instant messenger and had gotten my crush’s screenname from a friend. I worked up the nerve to start a conversation with him and soon after some awkward small talk he sent me a message in Comic Sans, black background, red lettering, and in French. I then went to google for translation and found out he had just called me a pig, in French. Being a seemingly awkward and chubby teenager, I was literally crushed.

The heartbreak was only made worse by remembering that a few weeks prior I had selected to take French class the next year and couldn’t change it.

Years later now that I’ve *blossomed* he follows me on every social media platform, has reached out a couple of times to try and flirt/hang out. Hard pass.

I believe he’s moved away and is a teacher now.

Image source: breezylova


One of them is homeless and a druggie. It’s very sad.

The other one is famous in his home country, is a best selling author, and is regularly on tv. Don’t have a crush on him anymore, but I’m glad we are still friends, and I’m happy for how well he’s done.

I guess they balance one another out.

Image source: secondofmyname


Image source: anon, Pavel Danilyuk

Dead by 32, drugs


Image source: USPO-222, Cody Portraits

My only GF in high school was my crush. Her mom banned her from dating me after about a year because my GF admitted to her mom that we were fooling around. This was about 20 years ago.

She’s still living with her mom, no kids, and as far as I know never again dated seriously after her mom broke us up. Still has the same job from high school too. It’s like her mom went way into protective overdrive and my former GF never grew up.


Image source: theMycon, Tima Miroshnichenko

He had a rollercoaster of a life. I admire him more than ever, and more than most people I know, but can’t wrap my head around why I ever found him physically attractive. Maybe it was always just his heart.

By age 25, he had a PhD, a wife, and was a captain in the navy. By 30, he had two PhDs, a small business where he made a metric a*s-ton of money, and his wife was pregnant. By 31 he was diagnosed with stage-4 skin cancer that swiftly spread to his lymph nodes, bones, esophagus, and a few other places. He was told he had minimal chance of making it 5 more years. Even with the best health insurance money can buy, it still basically wiped him out.

Seven years later, he’s living a comfortable but not extravagant life as a civilian contractor for the navy, same wife and two happy healthy kids, and spends most of his free time advocating for better public health care.


Still cute as heck, one of the kindest and most sensitive people I know, and still one of my best friends 15 years later. He’s also recently divorced (his wife was gay but needed time and support to come to terms with it) and now he and I are slowly testing the waters :) What started as a crush has matured into a deep and rich friendship, and—however it may unfold—I’m so grateful to have that relationship in my life.

Image source: Snish_Woogis


Image source: Pineapple-dancer, Tima Miroshnichenko

Haha, my husband! Our first marriages didn’t work out and we reconnected after our divorces. If only I would have confessed I had a crush on him in high school, might have saved myself a lot of trouble… Lol


Image source: Pixie_gurl, cottonbro studio

My crush turned into a self-righteous prick who still lives with his parents. He became livid when he found out my husband and I had a baby. I apparently was supposed to be his back-up plan if he couldn’t find anyone better.


Image source: chinchenping, cottonbro studio

You made me check and she is actually a very successful artist and an art teacher at a renowned university in France. She even got decorated for her work (Chevalier des arts et des lettres)


He’s an attractive gay man. I am none of those things

Image source: MelScarn




Shanilou Perera

Shanilou has always loved reading and learning about the world we live in. While she enjoys fictional books and stories just as much, since childhood she was especially fascinated by encyclopaedias and strangely enough, self-help books. As a kid, she spent most of her time consuming as much knowledge as she could get her hands on and could always be found at the library. Now, she still enjoys finding out about all the amazing things that surround us in our day-to-day lives and is blessed to be able to write about them to share with the whole world as a profession.

Got wisdom to pour?



crush, high school, hindsight, reflect, relationships, self-reflections, thenvsnow
Like deMilked on Facebook
Want more milk?
Hit like for a daily artshake!
Don't show this - I already like Demilked