How can I muster up the courage to ask my friend out?

[LuckyZebra]

I just wanna start by saying that this woman is beautiful beyond words, like she has MANY MANY options. I fear she won’t want an inexperienced virgin guy such as myself. That said, I’ve known her for fourteen years and finally developed true feelings for her 2 years ago.

When my father commit suicide at age 20, it sent me into a huge mental breakdown that took forever for me to recover properly. I finally went back to finish undergrad at 25, and graduated last spring. She never left my side even at my worst and I don’t think I ever will be able to repay her for that. There were days when she was my only friend in existence, this is why I love her so much now
.
I don’t want to explain all this to her, it might be too much. All I want to know is how I can ask her out without risking ruining the friendship. I really love this woman, not just because of her beauty, but her nature. But she usually goes for experienced men which is one thing I am not.

You wont be able to do it completely risk free. And if she's never given any indication she fancies you then .... be grateful to have such a good friend :)

Try telling her that you're thinking of dating, see what her reaction is. Dip your toe in the water, and come out if its too chilly.

When you ask her out you'll be changing the nature of your relationship. She obviously sees you as a good friend and nothing else.

Has there been any indication whatsoever from her that she is attracted to you? If not, I wouldn't ask her out.

You will ruin friendship only if you ask her out and start being a dick around her if she turns you down.
Also, tjere is a chance she already knows you fancy her as most men get obvious when in love.

Ask a woman out who isn't your friend.

I wouldn't risk your great friendship for a potentially empty romantic pursuit unless you are 100% prepared for it to go either way.

If something is there between you, it would flourish naturally without the need for you to profess your emotions bare.

Sending you all of the best! 💐

What's the rest of your life like now?

If you're now in a good place mentally, and have other friends of your own, hobbies and interests, etc, then maybe take a risk and ask her.

But if you're still quite dependent on her for support, then the dynamic is wrong for a romantic relationship.

Trying to turn the friendship into a relationship is always going to be a risk. There's no way to remove that.