What did I mainly do wrong by asking this woman out?

[SpiritedAwayfromHell]

I did something that was basically a death wish. I am 26M and still a virgin. And I confessed feelings to a woman who (and I don’t usually use the numbering system) is a straight up 10/10. Here’s the catch, she’s been my best friend since 2014, so it’s a long stretch from some woman I met in a bar. I don’t normally use the ?/10 rating thing but I need everyone to know the type of woman I’m talking about.

 

I was afraid to do it for a while because most people on and offline think a male virgin should lower his standards. But I realized how f***ing hard it is to find a genuine connection like what me and this woman had. She was my friend even when I was at my worst, for seven years after walking in on my father’s corpse. So walking in on that sight annihilated my sex drive and that’s why I ended up being a virgin at my age. 100%, I didn’t want to lose it until I recovered from everything, even if it meant redoing college.

 

I wanted to ask her out for years, but I wanted to build a future I’m proud of first. That’s why I spent 3 years redoing school, getting a decent degree, and therefore the resources to get an actual job that makes me able to live decently. Before I get “bro you thought she was a golddigger”, no, it wasn’t about that. Most people in general want their partners to be well off, so that’s what I tried to bring to the table.

 

Now that I’ve been able to make real money, and I knew she was single, I figured I’d shoot my shot. I was shocked she was single, but then it came to me that she was frequently used as a trophy by older men who have had practice hiding their true nature.

 

So far, I haven’t heard back from her.  I want to know what my biggest blunder was.

[Gina2005]

I don't understand.

You confessed your feelings to her, but, what was her response?

[Gebidozo]

I’m very sorry about the tragedy that happened to you. And I think it is great that you have recovered, took control of your life, and did something to make it better.

About the biggest blunder. First, it is still possible that she’ll reply with an acceptance of your proposal. It’s too early to call what you did a blunder, we don’t know the results yet. That said, I think that there are several possible big blunders here that perhaps you’ll learn to avoid in the future:

1) Friendship and romance are two very different things. Having been friends with her for too long, it is probable that this “friendzone” is inescapable.

2) It’s always better to show you have feelings rather than to confess them directly. Like they say to writers, “show, don’t tell”.

3) Confessing your feelings through text is not a good idea. If you confess anything, then only face to face.

4) You shouldn’t lower your standards just because you’re a virgin.

5) The part about her being used by older men as a trophy sounds alarming. Could you please elaborate?

[Gebidozo]

5 minutes ago, Gina2005 said:

I don't understand.

You confessed your feelings to her, but, what was her response?

The way I understood it, the OP confessed in text.

Otherwise he’d know what her reaction was.

[SpiritedAwayfromHell]

20 minutes ago, Gina2005 said:

I don't understand.

You confessed your feelings to her, but, what was her response?

There wasn’t one.  And there probably won’t be.

[SurfCity]

1 hour ago, SpiritedAwayfromHell said:

but then it came to me that she was frequently used as a trophy by older men who have had practice hiding their true nature

How did this information "come to you"? Rumors and gossip can't be trusted especially about beautiful women. People tend to spread rumors because they're jealous that they don't look like her or are angry that she rejected him. So, unless she told you that, I wouldn't believe it. 

In the future, don't confess feelings, ask for a date. It's usually better to ask out in person, but it can be done by text. 

Be proud of yourself for going back to school and getting your life in order. That's a big accomplishment. 

Edited April 16 by SurfCity

[ExpatInItaly]

4 hours ago, SpiritedAwayfromHell said:

she’s been my best friend since 2014

So she's your best friend, but you had no idea she was single?

4 hours ago, SpiritedAwayfromHell said:

I was shocked she was single

How well do you actually know her? How frequently do the two of you communicate? I ask because there seem to be some missing pieces here. This leads me to wonder if your confessional might have come out of the clear blue to her, and she doesn't know how to respond. 

 

[Foxhall]

the desire to feel loved by someone we admire is a natural part of our existence.

 its good that you mustered the courage to show your true feelings, you do not have to hide from them.

[FredEire]

You biggest blunder was putting her on a pedestal as a "straight 10/10" and earning money not for yourself but just with the purpose of impressing her.

It can happen that friends eventually become lovers, but generally when this happens both people respected that it was a friendship and it mutually changed to something else along the way. If one person is secretly desiring something more the whole time, orbiting and hoping for any scrap of attention, it rarely works out because they're putting the friendship second and the imaginary relationship first.

I think you probably need to move on from this one. If she's still open to being friends cool, but just accept it for what it is, a good friendship. You need to get out there and get some experience meeting different women instead of hyper-focusing on this one girl you've built up in your head.

Also from what you said your love life seems to have been badly held back by your trauma. I would say it's essential you explore this in therapy if you haven't already because it's going to continue to be a problem for you.

[FredEire]

On 4/16/2025 at 1:35 AM, Gebidozo said:

I’m very sorry about the tragedy that happened to you. And I think it is great that you have recovered, took control of your life, and did something to make it better.

About the biggest blunder. First, it is still possible that she’ll reply with an acceptance of your proposal. It’s too early to call what you did a blunder, we don’t know the results yet. That said, I think that there are several possible big blunders here that perhaps you’ll learn to avoid in the future:

1) Friendship and romance are two very different things. Having been friends with her for too long, it is probable that this “friendzone” is inescapable.

2) It’s always better to show you have feelings rather than to confess them directly. Like they say to writers, “show, don’t tell”.

3) Confessing your feelings through text is not a good idea. If you confess anything, then only face to face.

4) You shouldn’t lower your standards just because you’re a virgin.

5) The part about her being used by older men as a trophy sounds alarming. Could you please elaborate?

Also I'd say if it's true that she was dating older men who used her as a trophy she's likely got a lot of daddy issues going on, thereby making her even more unobtainable and feeding into your frustrating fantasy.

It seems a pretty common thing that guys who fall into the friendzone attach to the most unobtainable woman, a kind of "damsel in distress". You feel like you can fix her, and by extension fix yourself.

[enterthevoid]

 

 

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confessed feelings to a woman

"Confessing" is usually a bad idea.  You're dumping a lot of emotions you pent up onto someone, while they haven't had time to date you or really get to know you.  I think it would've been better to say that you like her and want to go on a date to get to know her.  It's lower stakes, lower pressure and lets her take things at her own pace.

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I wanted to ask her out for years, but I wanted to build a future I’m proud of first.

This is why it's best to ask someone out on a date as soon as you feel attraction toward them.  This way, if they say no, you get it over with after a week, rather than stretching it out for years.

Life would be a lot easier if you just ask someone out in a week, get the no, and then spend the next few years dating other people.  Instead of putting all of your emotion into someone who isn't interested.

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Most people in general want their partners to be well off, so that’s what I tried to bring to the table.  Now that I’ve been able to make real money

There are a lot of lower income and working class people who are dating or married.  There are also lots of people without degrees in happy relationships.  This belief that you need to earn a high income or get an advanced degree in order to date is just a rule you added that's not necessary.

I don't think there's anything wrong with being a virgin, but I think part of the reason why you haven't gotten much dating experience is because you have all these strict rules you feel like you must do before you feel like you can date.  This is like a form of perfectionism-based procrastination.

 

 

Edited April 17 by enterthevoid

[smackie9]

You need to seek out therapy for this. Getting your schooling together, and stuff is just excuses to avoid intimacy. It's not her, it's the fear of intimacy that's holding you back.

[Alpacalia]

She’s likely processing. You dropped a bomb on a decade-long friendship. If you tied your feelings to your financial stability or “being ready” now, she might wonder: Was this a negotiation? (“I’ve fixed my life, so now I deserve you.”) Women—especially those used as trophies—hate feeling like a reward for someone’s self-improvement arc. Your trauma, your career, your virginity… none of that is her responsibility to fix or validate. Did you make it about her, or about your journey?

You’ve survived hell. You rebuilt your life. That grit matters more than any romantic outcome. If this doesn’t work out, you’re still whole. If it does, take it slow—friendship is a strong foundation, but rushing to “fix” your virginity or trauma through her will backfire. Let things breathe. 

[enterthevoid]

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You dropped a bomb on a decade-long friendship. 

This. 

It's dishonest to act like you want to be friends with someone when you want to date them.  The honest thing to do - if you have feelings - is to ask them on a date (sooner rather than later), so they know what you want.

Imagine if someone wanted to sell you a car.  But they decided to be friends with you for months or years.  And then all of a sudden, they say they're really talking to you because they want to sell you their car.  But you don't need a car.

You'd be upset.  Why didn't that person just tell you from the beginning that they wanted to sell you a car?  You could've just told them from the start you weren't interested in a car.  It would've saved them a lot of time.  And saved you a lot of time.

Edited April 21 by enterthevoid

[SpiritedAwayfromHell]

On 4/21/2025 at 10:11 AM, enterthevoid said:

This. 

It's dishonest to act like you want to be friends with someone when you want to date them.  The honest thing to do - if you have feelings - is to ask them on a date (sooner rather than later), so they know what you want.

Imagine if someone wanted to sell you a car.  But they decided to be friends with you for months or years.  And then all of a sudden, they say they're really talking to you because they want to sell you their car.  But you don't need a car.

You'd be upset.  Why didn't that person just tell you from the beginning that they wanted to sell you a car?  You could've just told them from the start you weren't interested in a car.  It would've saved them a lot of time.  And saved you a lot of time.

What if they befriended you, but decided AFTERWARDS they wanted to sell you the car?

 

besides, the point of selling a car is to get rid of the car, collect money, then never see the buyer again.  There’s no feelings beyond that, only money.  So I don’t understand the analogy here.