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How the fuck do you break up with someone you're in love

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How the fuck do you break up with someone you're in love with? It's clear that it's the best option for me now, and the emotional side of me is not even being fulfilled, but I can't bring myself to do it out of respect for what we used to have and hope that it could be like that again in the future if I just put up with everything long enough.

We started dating when I was just barely an adult, and I was together with her for almost five years. We lived together that entire time. She was there with me when my heart condition developed and helped me when I thought I was dying, she was the one who encouraged me to go back to school, she's the only person in the world who knows all my secrets. She's beautiful and smart and kind to most people, she's into the same things I'm into and has a level of intelligence that lets me discuss things with her that I can't successfully discuss with others

Almost three years ago we broke up, and I've been a mess since, chasing after her non-stop. She said she needed to figure out what she wanted, and I did everything in my power to convince her she wanted me. I followed her around and did anything she wanted for two years. When I tried to force her to make a choice, she said "maybe". And that was enough to keep me going. Later, I was determined not to take "maybe", and she told me "probably". Eventually, I told her it had to be yes or no, and she told me "yes"... but with vague caveats. We're dating now, but I'm "on trial". Her conditions have no expiration date and no quantifiable goals, and there are no clear limits on what "on trial" means. Nothing has changed since before she said yes.

I have known for every moment since we broke up how pathetic I am acting. I'm burning up my youth chasing a woman who doesn't want to be with me but doesn't want to be without me.

I talked with her about it the other night, and laid out my concerns. I told her I needed to understand that she had feelings for me and I needed to understand what "on trial" was and how long it would last. She said nothing and started to cry, and I backed off. She said nothing on the subject the entire night, and now, weeks later, still hasn't.

It's clear to me that I need to separate myself from her, as she's never going to give me the words I need to hear to give up, but I can't bring myself to do it. The ridiculous hope that I can have back what we used to be, even if it's a hundredth of a percent of a chance, keeps me from acting against that possibility.

How the fuck do I bring myself to do it? I don't want to be without her, and I don't want to hurt her or make her cry, but I can't fucking take this anymore.
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Love is not enough.
Fuck OP it sounds like you're really dragging her down with you in this downhill slope of depression. Maybe just accept the fact that she'd be better off if you guys had your space for a while and she could think clearly without you trying to force your way back into her life. If you love her, let her go and if she loves you she'll come back.

What I'm trying to do is let her go.
Yeah, sack it up and do it. Stop being a pussy. Your procrastination is only prolonging your suffering.

That's some hot advice there, friend. "Just do the thing you're trying to figure out how to do". Thanks for that one, I think I'll get it written on a little throw pillow.
Fine then just sit on your ass and wallow in your self pity then instead of fixing your problem. You already know why you shouldn't be together and you already took a break once but you fucked that up before.

why did you two break up the first time???
OP maybe take some time to really think about why you want to be with her so much. Is it cause you're afraid of being alone? Is it cause you think you can't do better?
There are other girls out there man, so stop being a sad cunt.
You are definitely doing something wrong. She should be chasing you instead of the other way around.
First of all stop acting needy.
It will only make you look pathetic.
>obviously only girls should be chasing the guys!
>there's other girls who you've never invested years of resources and time you'll never get back that you can get with, stop being such a beta! ayy
Get the fuck off your 4chan mentality, stereotypes aren't as common IRL as you'd want them to be and sometimes things are a bit more complicated than the things you see in movies.

OP I've got a few things to say to you; firstly, don't give up. It's obvious that you love her. It's also obvious she's a heartless bitch who would rather toy with your emotions than give you a shot.
But that's life, and unfortunately we don't always get to control who we fall in love with.
The truth is you don't need her but you need to keep chasing man. It's only until you burn out that you'll learn your lesson.

I still want to know why they broke up. They were together for five years(!), even lived together, and it sounds like they had a really great relationship.

Then bam, three years ago they apparently broke up, but OP never explained why.
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