Hi everyone,
I'm sorry for jumping right in (haven't even posted in the intro room yet

), but I'm hoping to get some advice. I've been in an on-off relationship for about 8 months - a few months on, a few months off, you get the idea... When we first met, I was completely in love with her despite how different we are, but as time went on, we started to have problems. I'll be the first to admit that much of what "went wrong" in the first iteration of our relationship was totally on me; I completely failed to communicate with her about my comfort levels and what I wanted out of the relationship. That said, she also failed to communicate, and accidentally put a lot of pressure on me. We broke up, and then mostly didn't interact for several months (though, I do genuinely care for her so, I worried a lot). After a break of several months, we got back together (I initiated), and once again, things were great starting out. Almost two months back in, and we're struggling... again.
I feel incredibly guilty. I feel like I'm treating her like a yo-yo "yes I want you, no I don't." And we are very, very different - I'm ambitious, she's apathetic, she's physical, I'm cerebral, and we don't share the same values. But... it isn't even these difference that make this not work for me. What makes this not work for me is this tremendous chasm I feel that separates us emotionally. We're both in our late twenties, but I often feel like I'm dating a teenage girl instead of a grown woman. She's simultaneously naive and incredibly nihilistic; she reacts to everything - sometimes in the form of (thankfully not physically-manifested) tantrums, and she whines/ pouts but refuses to do anything to improve her situation. None of these things make her a bad person, not even slightly. There's nothing *wrong* with her, it's simply that she's very immature for her age, and I grew up very fast so, we're not operating on compatible emotional wavelengths (contrast my description of her with the fact that I'm pragmatic, pantheistic and humanistic, generally non-reactive unless already emotionally compromised, and I tend to sulk or self-isolate while reflecting on every possible way I can imagine to change whatever negative situation that I'm in). It's not that I'm all-wise or completely done learning, far from it, but even on my most immature days, I still feel like a grown man dating a teenage girl, and that simply does not sit well with me despite knowing it to not technically be true.
[To clarify in case anyone is wondering, no, I'm not looking to date someone else right now - actually, I don't think I'm in a healthy enough mental state right now to be in a relationship. Also, there's no issue with physical attraction between us].
So, why am I asking for advice on the internet? Mostly because I don't want to involve our mutual friends any more than is necessary in what will inevitably be our second and final break up. I could ask my other friends, but they'll be too biased and think that I should simply break up with her ASAP, and I don't see that as a reasonable option.
My question is this: is there a "kind(er)" way to break up with someone? Is it better to wait and sort of gently taper off the romantic side of our relationship? Is it better to be upfront and make a clean break? I'm inclined toward the former, especially given that I do want to stay friends with her (I do love her, we're just not romantically compatible) and also because I'm helping her financially right now (and don't want a break up to interfere with helping her get on her feet). So, what can I do? I've actually never broken up with anyone before, and I'm really uncomfortable with doing so, but I'm deeply dissatisfied in this relationship as it stands. Help?
Thanks,
Josh