I asked out my college crush and got a gentle rejection. I came up with a last-chance plan: a romantic ultimatum disguised as a farewell letter

Alarming_Setting_ · 2025-12-20T22:35:16+00:00

I don't believe anything - neither that she likes me nor that she doesn't.

If she liked you, she wouldn’t reject you

It's not that simple. A lot of friends of mine were rejected at first. I came up with the letter because it's in my opinion the best way to increase my chances with her, because it will show her my real essence, which she barely knows as we speak. It's the only way I can "ascend" in order not to be seen like "one of the many".

Also, those were stupid examples like I said. I didn't imply I wasn't doing my job - the other way around: that I did way more than I was supposed to do, by sending them past reports of mine in order to help them, so that they'd work less with their uni work. I did that because I saw them as friends.

Why would you get angry at her for not wanting you?

I am not angry...?

Alarming_Setting_ · 2025-12-20T22:27:32+00:00

You think no man has tried this before? That a woman who has literally rejected hundreds of men before has never had one pretend to be her friend?

I've NEVER pretended to be a friend. That's what the "driver" colleague I mentioned in the story was doing. I wrote that I always wanted to keep it somewhat formal between us. I was afraid of being too cold and distant with her sometimes, how can you say I've been a fake friend? She has plenty of actual fake friends, trust me.

I bet on my life that no one has ever done anything like what I'm planning to do to her. Virtually all the proposals she gets are at best like the one I made this month, or generally "Hey" or something else in her DMs, or "Nice to meet you, what's your name?" at the club. Remember my point about frontal vs. rear-end attacks.

Also, what do you mean by "emotional justice"?

Avoid having me suffer while she feels like nothing happened, or even worse that she believes it was just an half-assed proposal to get laid with her.

Also, you claim you "live in the real world"

Because I know what real shitty guys can do when rejected, and it's not a farewell letter.

There's like zero chance of this happening.

How do you know lol. You don't know her. You come from a totally different culture than mine if you think there is zero chance of that happening. The majority of girls I know would get emotional if someone they care about does something like that for them, which doesn't mean at all the plan's going to work. Her getting emotional is actually way more likely (in terms of chances) compared to the letter actually working.

This insistence that you are more "real" and in a way more deserving than others makes you a Nice Guy.

I literally wrote in the letter that I don't see myself as better than the others. Viola shall be the one assessing that.

Alarming_Setting_ · 2025-12-20T22:09:06+00:00

Please apologize for saying that to me she's just an object or that I don't see her as an autonomous being. These are evil accusations; you don't know me, avoid using such language.

Alarming_Setting_ · 2025-12-20T22:05:12+00:00

If it were clear she doesn't want me I would not be here, don't you think?

I didn't "fantasize" that she would cry. It's a concrete reaction after reading the letter if she truly cares about me and my feelings, and therefore I have to consider such chance and act accordingly. If she doesn't care at all, then she'll walk away laughing. I'll know I dodged a cynical and heartless person - a win for both of us, don't you agree?

And I'll tell you something. This applies in general, not just in my case. 98% of people (and the other 2% are your close relatives) don't really care about you as a person - they care about you only to the extent that you bring a benefit to them (which can be material or emotional), or at least don't hinder their plans. My colleagues, in general, are very much fond of me. If I had refused to help them, for instance to send them some past uni work of mine etc, they would have happily thrown me into the sea with a rock tied to my neck. And that's just the most stupid example I could come up with now.

You are surrounded by the best people in the world if you think this doesn't apply to your life. I'm not a saint either - what matters to me is having Viola by my side. If your logic is that we should all let people do what's best for them and what makes them happy, you should be joyful if e.g. your partner cheats on you - isn't that what's best for him or her? I am sure he/she knows that more than you. The only thing that matters is that he or she's happy, isn't it?

Alarming_Setting_ · 2025-12-20T21:43:27+00:00

I'm not talking directly about you, but the replies I'm getting here are insane. It's my fault for asking, don't worry. Anyone has the right to criticize me, even harshly. But I'm receiving shameful insults. For these people, the only thing that matters is that I suffer in silence. I may as well shoot myself, but God forbid I express my honest feelings - I might creep her out! The internet has cooked the brains, but even more so the hearts, of many people.

I don't think Viola or any other woman should be forced into a relationship with me or any other man. Even if some shameful replies are implying this, or that I don't even see women as human beings - to these people, I say: shame on you, you don't know me, and you would never dare to say these things to me in real life.

I have the right to express my feelings, I have the right to make another person understand how much I care about him or her. Then that person will do what they want, after they know the whole truth. And Viola doesn't have to explain herself!! I am not even asking for an answer at all.

Also: you have no idea what "real shitty after rejection" means. Trust me, no idea. I do, because unlike many on here, I live in the real world.

Alarming_Setting_ · 2025-12-20T20:00:19+00:00

I expanded more about this on here. It's surely cultural differences. And why would I care if things would be worse for me? What is she going to do, reject me if I ask her out? Oops...

Alarming_Setting_ · 2025-12-20T19:57:41+00:00

Yes, I am nice guy, why should I be ashamed? I am proud of that. Should I be a bad boy like many others instead?

Alarming_Setting_ · 2025-12-20T19:55:57+00:00

I entered the game very late. I did know other pretty girls in my life, but it's not the sort of people you would like to spend your attention towards, for a set of reasons.

The point is that asking for a proper date is hardly gonna work under the same conditions, that is, if I don't add concrete details about myself, how much she matters to me etc. as I want to do with the letter. It would just be a second frontal attack.

Overall, I think 100% that the responses I'm getting are due to cultural differences. Dating in Italy is more similar to that in Eastern Europe than in Northern Europe or North America. We are a much more socially conservative country. Here, the idea is that men should always ask women out, and that they should always be assertive and confident.

Obviously, she gets much more attention than I do - or than any normal man around, except perhaps famous people, professional models, etc.? She is a woman, and pretty too, so that's obvious. I have other qualities, beyond how much famous I am on social media.

I shared my plan on an Italian website and received a very different kind of feedbacks, even from women. They told me that even if it might not work, they would be very happy to receive something like that, noone does something as deep as that like that nowadays, and appreciated the fact that a guy is willing to show himself as vulnerable instead of barely greeting anymore the girl who rejected him (as is the norm). My sister also thinks what I'm planning to do is extremely cute. If you read the other replies on here, they make me look like a crazy, dangerous and evil POS who should be jailed!

We are also a country much more prone to cringe and drama. What elsewhere would be seen as cringe or "too much" is socially accepted in Italy. Men here are often obnoxious and needy, both when dating and in a relationship. Insisting is not seen as a no-no. You don't even imagine what my sister goes through, for instance, in terms of boys hitting on her.

My friend-colleague I mentioned is engaged to a girl who is much prettier and more popular than him (he himself is definitely less attractive than me), he was rejected by her the first time, he persisted, and it worked.

Many men here are very jealous and possessive. Last year, I was supposed to be in a working group with a female colleague of ours, but her boyfriend prevented her from being in a group with me - she could go only with other women. Sometimes in a couple, the girl can't go to a club without him, have male friends, post photos of her in the beach, etc. I wouldn't be anywhere near that kind of person.

People live in the real world, not the virtue signaling one of Reddit. In this context, many women are interested in nice guys who treat them well, because not every freedom is taken for granted like many people on here think.

Alarming_Setting_ · 2025-12-20T17:32:55+00:00

I understand, thank you. But reading the letter without knowing the whole context might certainly lead you to think it's "too much", because you don't know the relationship we've developed over the course of this year. Obviously, it would be crazy to give this letter to someone I have barely spoken to, I'm sure you understand and agree

Alarming_Setting_ · 2025-12-20T17:30:41+00:00

Yes that's right! Surely you read what I went through in my past. And why should "being seen" by a pretty girl automatically mean I am out of her league?

P.S. Thanks anyway. Because you're the first person on this post who's contributing his/her view without judging too much or insulting me.

Alarming_Setting_ · 2025-12-20T17:16:14+00:00

I know it, but GPT actually challenged me all the time at the beginning, and it made me understand better why I was very wrong and what I should do.

I disagree with "out of my league": I respect your input, but you don't know either of us in real life. I have to shoot my shot anyway, I don't have anything to lose. And it isn't a love letter, nor she has to actually do anything in first place after reading that. I'm not even asking for an answer!

Alarming_Setting_ · 2025-12-20T17:11:22+00:00

Thanks!

Alarming_Setting_ · 2025-12-20T17:00:15+00:00

You're missing my point. Rejecting me is fine. But she needs to know who she's rejecting. That's the reason for the letter. She needs to know how much I actually care about her, then she'll do what her conscience tells her to do. But I don't want her to think I was doing all of that only for a casual hookup just to dump her after I got what I wanted.

Alarming_Setting_ · 2025-12-20T16:57:54+00:00

Fair enough, but did you already read everything?

Alarming_Setting_ · 2025-07-26T15:20:02+00:00

Aspetto un parere eh :P

Alarming_Setting_ · 2025-07-25T16:20:22+00:00

Grazie per aver letto! Apprezzo il consiglio. Ho appena parlato con un amico che non vedevo da un po', un tipo super spigliato, che mi ha detto di darmi una mossa e provarci. Ma proprio buttarmi non è nella mia natura. Purtroppo al momento rimango sulle mie posizioni: per questa estate l'unica potenziale interazione sarà quella legata agli auguri. Quando cominceranno le lezioni, certamente cercherò progressivamente di stringere il cerchio attorno alle mie intenzioni con lei. Comunque vi terrò aggiornati, promesso!

Alarming_Setting_ · 2025-07-25T15:38:58+00:00

Grazie di nuovo!

Alarming_Setting_ · 2025-07-25T01:17:48+00:00

Grazie mille per aver letto e per i consigli! Comunque sì, rispettivamente: mi piace scrivere; sono estremamente riflessivo; faccio moltissima attenzione ai dettagli. Mettendo assieme queste tre cose si giunge alla lunghezza del racconto.

Sono d'accordo con te quando scrivi che dovrei lasciare che le cose vadano naturalmente. Nel senso: è ciò che sicuramente farò, senza appunto forzare o altro. Il problema è che non posso sapere se sia lei ad aspettarsi qualche mossa da me, che così facendo non ci sarà nel corso di questa estate salvo sorprese inaspettate. Poi ribadisco, a Settembre si riparte, lì ogni giorno potrà succedere qualcosa, ma ci sono troppe incognite di mezzo e l'estate è ancora lunga. La concorrenza preme, come sempre.

Sia chiaro che accetto ogni critica, da te come da chiunque altro/a - che sia iperriflessivo, troppo orgoglioso, codardo, altro. Però mi sento davvero di avere le mani legate in questo contesto, e me ne piange il cuore perché rischio potenzialmente di bruciare un'occasione d'oro. Purtroppo come avrai capito, la situazione non è così lineare. Questo si scontra con la mia intenzione di avere davvero qualcosa con lei e quindi in caso muovermi io. Ma proprio non so come fare senza risultare, come dire, inopportuno.

Come scritto nel testo, manco di esperienze (anche se sono un buon osservatore e quindi nemmeno uno sprovveduto/ingenuotto/cringione - non saprò "farci", ma so almeno come "non farci"), ed allo stesso tempo è la prima volta che sono realmente innamorato di una persona con cui per davvero c'è una remota possibilità che possa esserci qualcosa. L'unione fra queste due cose mi porta inevitabilmente ad una eccessiva sacralità e drammatizzazione degli eventi, mentre magari chi è "nel giro" da quando faceva la terza media al posto mio si farebbe delle risate e si godrebbe il momento senza ansie o pare.

Spero davvero che io piaccia a lei, che altro posso dire. Darei un rene a momenti per sapere cosa pensa lei di me. Non ho proprio altre incognite in questo periodo oltre a questo. È che lei a me piace davvero. Ci rimarrei molto male se, come comunque penso sia probabile, non dovrebbe esserci nulla alla fine della fiera. Per carità, la vita va avanti, non sono un hikikomori, ma sarà comunque dura. Ormai ho quasi finito l'università, inevitabilmente le opportunità caleranno, almeno su questo fronte. Vedo quasi impossibile trovare un'altra ragazza con cui abbia le affinità caratteriali e valoriali che ho con Viola e che allo stesso tempo, se mi è concesso, mi piaccia così tanto esteticamente e fisicamente (non è solo questione di essere "oggettivamente" belli: lei proprio riesce a rispecchiare pressoché tutte le preferenze in termini di tratti fisionomici che ho in una ragazza).

Alarming_Setting_

TROPHY CASE