Lucky You

Poor little loverboy,
Drowning in an ocean of pain,
Fooled by his heart,
And he's not the only one.
--
A path if destruction traced in his footsteps,
A path of love led by his heart
Lessons learned with a bitter regret,
So he can now find his part.
-
Past mistakes now play ammunition,
Loaded in the realist's gun.
Ready to take aim at the dreamer
To shoot down his hopes of the one.
-
Poor little love filled soul,
Your heart's been worn so much before.
Your mind persists to no end,
And you don't know what you're doubting for.
--
Learning to fall back on your heart,
Learning to know to not compare.
Comparing spells out the word desire
For the past souls which you once loved.
--
Poor little tortured boy,
First fools gold, but now it's true
You realize you had it all along,
The one girl rightly pursued.
--
Silly little cliché thoughts,
Running through your mind.
Yet cliché can never apply,
To any love that's true.

I liked it, although I thought in some places your flow was destroyed

Hey Timmy! Evi here.

Drowning in an ocean of pain

I like your first stanza's ideas, save for this. This is angsty and clichéd, so find a more original way to show the pain that results from being fooled by his heart. And the best way to do that is to force yourself to avoid mentioning words like "pain" or "hurt" or "agony" or "betrayal", so instead you have to show the emotion.

A path if destruction traced in his footsteps,
A path of love led by his heart
Lessons learned with a bitter regret,
So he can now find his part.

What does this mean? You're listing things; subject phrases without verbs, basically. A path of destruction...okay, what about it? A path of love...does something, is something? Lessons learned...so this means what? And why can he "now find his part"? What is "his part"?

This stanza as a whole is structurally unsound, and really doesn't say anything if you look below the words. Either make the sentences go somewhere or replace/cut this.

Past mistakes now play ammunition,
Loaded in the realist's gun.
Ready to take aim at the dreamer
To shoot down his hopes of the one.

Much better! Cohesive statement, interesting analogy-- good. The only thing I didn't like here was "the one" on the last line. It's obvious that you just stuck it in there for the rhyme scheme, but even that (your rhyme scheme, that is) is irregular. Stanzas one, five, and seven don't have any rhymes-- why must all the others? Either use a rhyme scheme or don't worry about it and let the words flow.

Poor little love filled soul,
Your heart's been worn so much before.
Your mind persists to no end,
And you don't know what you're doubting for.

In the first stanza you spoke of the loverboy in third person, saying "he". Here you use second person "you". That shift is fine-- in fact, it has the possibility to be very meaningful --but make sure you know why the narrator is suddenly speaking to this character when they weren't before.

And those last two lines don't mean anything, either. Read them to yourself, and look under the words-- what message are you actually conveying? doubting what for? Mind persists about what? It's too vague to give us any meaning or imagery.

Learning to fall back on your heart,
Learning to know to not compare.

Again: so what? You have bits and pieces of complete thoughts right now. These phrases don't go anywhere or do anything. What about learning? Are you telling him he needs to learn these things? Are your narrating what happens when he begins to learn these things?

Overall

I think the idea behind this definitely has possibility; just work on the execution. In each stanza, think about one concrete thought or image that you're trying to get across, and find a clear, grammatically-sound way to say it. You're beating around the bushed throughout this. The last stanza didn't seem to fit so much-- everything else is about past loves, regrets, searching for "the one"...but then clichés? It doesn't naturally progress to that final point. Make sure you either have a connecting stanza, or rework it a bit so that it flows from one idea to the next.

Best of luck, and PM me for anything!

~Evi