Would this character be classified as a Jerkass?

Here. I'm trying to enforce a personality which is cold and guarded but warm deep down for this character, but as the story flows, I don't want him to come off as an asshole but more like a cynic.

Doesn't seem like a jerkass to me. If he was, then instead of saying to himself that love is disgusting, he'd probably go around mocking people for thinking love is swell. Like "Nyah-hah! Love sucks and you suck for liking love!" Or just plain forcing his opinions on someone. As in, "Love is disgusting, and anyone who thinks otherwise is dead wrong."

By the sound of things, he's also got a reason for thinking poorly of love — not just hating love because it exists. In my eyes, that certainly helps.

I agree.

"At the end of day, I couldn't complain nor do anything about it; it's their lives, and if they're happy, then why should it matter what I thought?"

I think that's a pretty telling line. A real jerkass wouldn't think something like this. They'd perceive the negativity as definitely external - "Love is disgusting" rather than internal "I am disgusted by love". Although admittedly he does later return to the former view, the acknowledgement that just maybe it's a subjective matter is enough to stop him seeming too unpleasant.

It's hard to tell from just this though - I think the crucial difference between a cynic and an asshole is how they interact with others: an asshole indiscriminately inflicts his negativity on everyone around him, while a good-hearted cynic will generally try to bottle it up unless someone actively asks for his opinion, or unless he thinks someone really needs to hear the truth for their own good. That's why the final line makes him seem more asshole-ish than the rest; he's speaking it aloud, and given that he's surrounded by many people, it's likely that at least someone will hear, even if he's just muttering to himself. That's upsetting people for no good reason, which is the action of an asshole.

It's a fine line though, I think people are willing to forgive someone a bit of assholery from someone under pressure, and it might be good to introduce him as an asshole, because then the contrast is more impressive when it turns out he's actually a nice guy.

Bottom line, actions speak louder than thoughts. Pet the Dog and you should be fine.