Yes, I know I shouldn’t be asking bitchers for advice. And this is probably boring, but what the hell.
I met a certain boy when I was twelve. He’s two years older than me. Many many years later, we are both college students, and I am just as in love with him as when I met him. Unfortunately, I was cursed with SHYNESS and have found it impossible to tell him how I have felt all these years. We have infinite things in common and have maintained a friendly and happy, albeit distant friendship.
However, it is nearing the time when I have decided to move overseas for a good while. I am thinking of sending him a letter telling him how much I love him, but I’m afraid of what the awkward consequences may be, and if this is a crazy idea or not.
Bitchers, I need your help. I have gotten much attention from boys over the years but refrained from any relationship whatsoever, all because of the one chance I could end up with this perfect man, that I’ve never stopped loving.
Bad idea? Good idea? Alternative idea? Help please.
This article appears in Aug 20-26, 2009.


I was where you were at one time.. this guy I met when I was 11- he was my first ‘boyfriend’. We necked once, which I stopped out of repulsion ( I was still playing with cabbage patch kids). Then one day I broke up with him after he grabbed my desk at school when being chased and left behind sweaty smears with his freckly, oniony-smelling hands. Well anyway, 2 years later I started to develope strong feelings for him- feelings that caused me to tape signs to his bum and take running kicks at it. I was completely in love with him and remained that way until I was 17. I was fixated but he never knew it. I eventually forgot about him when I met my stupid Enrique Iglasias lookalike skateboarder boyfriend in grade 12, and I forgot about him. After a few more long-term relationships, I’m now with the man of my dreams, someone new. My advice might not suit you, but what about waiting for your travels to end before saying something to him? I don’t see what you have to lose by telling him- seeing as how your friendship is distant- except this potentially amazing experience which might even find you a man you’ll be even crazier about. You’ve gone this long, why not have this adventure and then see how you feel? Maybe it IS the real thing, but then again, maybe there’s a real Mr Right that just hasn’t come along yet and that’s why you’ve not been able to forget this guy…you’ve been romanticizing him in your mind to the point where nobosy else measures up. This might be a bad idea. I hope I don’t sound too cynical bc I know it sometimes does happen the way you’re describing, but don’t you think it might be a good thing to open yourself to other guys, if only to make sure you really do feel the way you think you’ve been feeling for so long? Sorry this reply is a bit rambling- I need some caffeine. Good luck!
If your feelings are this strong it would be a tragedy to go through life without ever revealing them. Maybe he feels the same way or maybe your admission will make him realize feelings he never knew he had – even if it doesn’t end picture perfect I doubt he’d distance himself over it. Just be sure you do something before its too late.
Always wondering what could have been is much worse than any embarrassment, etc from telling him….let him know!
Scooby, you are very wise. After years of putting her love on a pedestal (she said he was perfect), how could he possibly measure up now? Even if that wasn’t so, unless she is prepared to stay or take him with her (if this is even a possibility), starting something is pointless.
I also had an infatuation from 12 years old until I was 22. I took the risk and let my ‘love’ know when I was about 18. We wrote from that time until we started preparing to meet up. Before the actual plane ticket was bought, I changed my mind. Why? Because I realized that he was now a stranger. I realized that the man I loved all these years did not exist.
But, if you feel that you will regret not taking any action, you can ask him if he would meet you for a walk, as you are going away for some time, and you didn’t want to leave without saying good-bye. You shouldn’t be afraid to tell him that you had a crazy crush on him in college (how can he be anything but flattered). If he cannot make the time to see you, there is unlikely a mutual feeling here, so that, in itself, will be an answer–and a resolution. But, if he does meet you, and he does express mutual feeling, still, tread carefully. Trying to live up to an ideal will only cause future heartache when reality deals you a blow to the stomach.
This may not be a break-up story but it’s mighty boring. Stop being such an idiot and tell him how you feel. If he blows you off then you can move on and find another “perfect man”, there is more than one out there.
“I have gotten much attention from boys over the years but refrained from any relationship”.
Clearly not enough attention as here you are sucking for more.
“refrained from any relationship whatsoever”?
Buy some porn…get fucked.
Go overseas first before you tell him, so you can have fun/experiences/meet other interesting people/enjoy your life. If you come back and you feel the same, tell him.
As others have stated: you have nothing to lose. Tell him OP, no regrets. And if he doesn’t share your feelings, well you get to be surrounded by hot foreigners overseas. Good luck!
Smiling at “many many years later, we’re college students…”
What’s that, like 7-8 years, lol? I got unopened mail older than that…
Move on…he’s a guy, and if he hasn’t tried to fuck you yet, he ain’t into you…
Besides, the more important question you need to ask is –
Who actually BUYS porn these days? What is it, 1988?
It is nice to see a man who is in touch with his feminine side, Frosty:
“…he’s a guy, and if he hasn’t tried to fuck you yet…”
Sounds like feminist theory to me = )
Are you hoping he’ll reciprocate your feelings? Leave with you? Be waiting when you come back? What are you trying to accomplish here, really? It doesn’t sound like you primarily just want to get physical with him, but hey if you do, put it out there, see what happens, then merrily (and safely) fuck.
Otherwise, seriously … what good can come of this? That gnawing feeling inside telling you this is a bad idea is right. Be an adult here. If you want to clear the air, see what’s there, have no regrets, you need to tell him face to face. It might not go the way you want it to, but at least you’ll have faced it head on and know where you stand without having to wonder for the rest of your life. The letter is the easy, cheap way out. You want to shelter yourself from any potential awkwardness and pain, but you need to have the confidence and courage to do this face to face.
There is also the chance this has more to do with yourself and your internal battles than him. Search your soul. Is their a gap in your heart? Your life? Do you feel incomplete, disconnected, lost? Scared when faced with the possibility of being alone? Think about it. You’ve known a “perfect” guy since twelve, love him, and never had a relationship and now as you’re about to leave you want to send him a letter confessing your love of him? You need to step back and allow yourself to realize how silly this sounds. Maybe it’s a trite romantic, but it’s silly nevertheless. Especially considering you describe the friendship as being “distant” and if this is more on his part than yours you have to be mindful of that. It doesn’t positively mean he’s not interested in you, but you have to be able to face the idea that it’s a possibility.
Lastly girls – contrary to popular belief – not all guys are uncontrollable horndogs who wear their hearts on their sleeves. Just because a guy hasn’t tried to fuck you isn’t the end all to be all of signs.
Mr Frosty may be a jackass, but he actually makes a good point. If this guy was interested in you, he would have made a move by now – he is a guy after all. Unless of course he’s just as shy as you OP, in which case, make a move.
Now I gotta ask: If you sleep with him, does that change your travel plans? Or are you moving away anyway, no matter what. If that’s the case, do nothing. Because then you’ll waste time being in a “long distance relationship” and won’t enjoy your travels, and potentially miss out on meeting someone really special.
If you tell him, you don’t have to make it a big, serious thing where you face humiliation. You could mention over casual drinks out one night, a bit playfully: “You know, I use to have the biggest crush on you!” You’ll see by his reaction if there’s any hope. But anyway, I’m one of those people who don’t believe there is only one potential soul mate out there- I think that over the course of your life, you will meet various people with whom you have the potential to fall madly in love with, and they won’t all necessarily be the same type. And tastes can change over the years; they guys I used to fall for in my early twenties were completely different from the ones I fancied in my late 20’s. There’s something to be said about sampling the menu before ordering- for me it was the dating and relationships I involved myself in that made it so easy for me to spot the right guy when he finally came into my life. At the time I was with him, I thought it couldn’t get any better than my first boyfriend…but then I met guy no.2… and with each subsequent relationship I was better able to tell what things were important to me in a relationship and which ones didn’t matter. Now I’m with someone who makes me really happy, hopefully for the rest of our lives.
One thing woman always asked the guy, “Talk To Me…”, Live by your gender’s words. I’m 1 and have been in MANY relationships, I didn’t talk my feelings, nor did i want to sound like a pussy to my girl. I guess is why i was in a lot of relationships. 2 years ago I sat and thought what i was doing wrong, and it was the no talkin for each one, I met this wonderful girl 2 years ago, and I tell her EVERY THING… She has now become my best friend my true love. Being honest with the other person is the best thing for a relationship. You been with this guy for quit some time, if your still shy to tell him how you feel, or don’t feel comfortable enough to talk to him by now, hell you 2 don’t beong together any ways so just pack ur bags, dont call him and just leave, or you can be a big girl and say what’s on your mind
Well. If you’re going over seas then it’s not like you have to see him at all, really, so the embarrassment of rejection won’t be as traumatic if there’s an ocean separating both of you.
I think if you’re going to tell him, you might have to risk losing his friendship. I’ve seen that happen many times. I agree with a couple other people, in that you should wait until you get back. Or, at least until you’re overseas for awhile. If you’ve been overseas for awhile and are still thinking he’s the one, send him a note, saying “hey, I’ve been thinking of you a lot since I’ve been gone” and tell him how you feel. If he doesn’t feel the same way, you can chalk your feelings up to homesickness and nostalgia. If he does feel the same way as you, you’re golden.
Damned if you do … he may not feel the same way.
Damned if you don’t … he may feel the same way.
sometimes the male of our species can be a real fool. we have all the signs, but fail to interput them.i had this happen to me a long time age, and believe me, if i would have acted on my first thought then,well i would be a lot happier now. not that i’m unhappy now, just happier. we are dealt a hand in life, and those of us that get the shitty deals, have to discards after awhile, to better our hands and our life. my vbest advice to you is move on, there is ultimately someone there for you somewhere. but here, i don’t think is the place. most here are too fucking hung up on punctuation, grammer, spelling and shit like that. you don’t need these kinds of fools. get out, and do what you feel you have to, to find mr. or miss right for you. fuck everyone’s ideal, pick your own, and try not to be overspecked.
Nothing ventured; nothing gained.
Fortune favours the bold.
Everyone dies; not everyone really lives.
Grab life by the balls and milk it til you get what you want….
You see where I’m going with this? Take a deep breath and TELL HIM. It is not a crazy idea. It is the one thing you may regret for the rest of your life if you don’t at least TRY!
Good luck.
Tell him before you go so you can get it off your chest! 🙂 If he hasn’t expressed interest in you over the years, this might be a clue that you may not get the answer you want. But there’s only one way to find out – tell him how you feel. 🙂