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Playing through headphones.

I live in an apartment complex, so I feel like a total ass when I play my crappy chops loud enough for the neighbors to hear.

The problem is that my amp is very quiet when I play through headphones. Would buying a more powerful one affect anything, or does that only come into play when hooking up to an actual speaker?

Now, the reason why it's so quiet is because I have a split going on. One line comes in from my computer to my headphones. The other comes from my amp to my headphones. I don't know why, but that makes it sound quieter. So I can't really turn up the music I'm playing along with too loud because then I can't hear myself.

I want to buy a better amp to fix the situation, but I don't want to get home and realize it doesn't make a difference. For the record, I'm not even using a bass amp at the moment, but a Roland Microcube. I left my bass amp at home when I moved out to grad school and only took my Microcube with me.

Should I just go with an amphead at this point and not bother with a combo or speaker?
 
Why not just plug the headphones into the amp when you want to play bass and plug them into the computer when wanting to listen to the computer? If you want to be able to listen to more than one source at a time, you need a mixer. You can find a cheapie mixer with a few channels online for well under $100. Trust me that a mixer is what you want.
 
Buy a Vox Amplug- the AC30 model sounds great for guitar or bass. You can plug a music source into the aux input and play along. I use this at home almost exclusively. Also, get a halfway decent pair of headphones for it; nothing too good, just not super cheapo ones. The AC30 Amplug even has decent distortion for bass if you dig that
 
I use Sony MDR-V6's. I love them to death.

Why not just plug the headphones into the amp when you want to play bass and plug them into the computer when wanting to listen to the computer? If you want to be able to listen to more than one source at a time, you need a mixer. You can find a cheapie mixer with a few channels online for well under $100. Trust me that a mixer is what you want.

Any suggestion as to which one I should get?
 
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I'm in the same domestic situation as you. I've got a G-K MB200 head (which I bought specifically because it has both a headphone out and an aux in). I have Grado SR-125 headphones (which are a bit bright, but it might be an impedance mismatch). Regardless, the setup works great for me. I can plug an iPod into the aux in and play along with tunes or a metronome app, and no neighbors complaining.
 
I have a Behringer 2442FX, which is on the big side of portable mixers and definitely overkill for your needs. It's the mixer for my small PA and I like it a lot. I have audio feeds from my desktop computer, laptop, drum machine, microphone and bass amp running into it. I do exactly what you want to do; play along with songs through my monitor speakers and headphones when it gets late. Personally, I find it challenging to play bass while wearing headphones, but that's just me.

Behringer mixers are a good value and are dependable. That said, any small 2-4 channel mixer with a headphone output (99% have a HP output) would fit your needs perfectly. A small mixer is a good investment for any musician, IMO.