settle a bet...?

They are confused and are attempting gross over-simplication. A regular telescope has no such capabilities.

My Understanding:
(Someone who is more astute about astro-physics may come along here and explain it better):

Hubble and other powerful super-high tech imaging devices have certain capabilites of seeing great distances ...light-years away. As a result, with the use of super-computers, they can trace the pathways of solar systems and the universe and mark how the universe is moving apart. That is not looking back in time literally -- it is predicting how the cosmos is moving now and has moved in the past.

The question is poorly worded. Let me clarify. The further an object is away from us, the earlier the light left. So you are looking into the past whenever you look into space, but the longer distance you are looking the further into the past you are looking.

1. If you are looking at a particular object. The light you are seeing now left that particular object in the past. You are looking into the past. Looking at that object through a telescope will give you a more clear image, but won't change when the light left that object. If this is the question, then you are correct and your roommate is wrong.

For example, if you see a star that is 50 light years away, then you will see the star as it existed 50 years ago whether you are looking through a telescope or not.

2. A telescope lets you see objects that you can't see without a telescope. It is easier to see objects that are close than objects that are far. So with a telescope you can see more distant objects meaning that the light left them must further in the past. So in this case your room mate is correct.

thanks for the reply you guys. I told him all that and more so i dunno. He seems to believe that by simply getting a more powerfull telescope you can look at the same object and see an earlier version of it. I told him you still have to wait for the photons to reach you but there is a fundamental misunderstanding here. Thanks dudes!

Remember - you can lead a horse to water but you can't make him think.

Sounds like your friend is getting confused by the fact that we are looking back in time when we peer deeply into space. Or maybe that's what they mean?

Yah i think thats the source of confusion here but its ok now. I think he half gets it now hehe. Looks like he just didnt feel like being wrong. Silly human pride I tell yah. Thanks again for my back, eh! (that applies to everybody who commented)

The telescope only improves your quality in absorbing and interpreting light, it does not anticipate it, it merely allows you to see it in a visible spectrum. Tell him to look up Red Shift phenomenon.

Forgive me Ched but earlier than what

If you mean than without the scope, no, you'll see it slightly later

Edited after having noted later posting

No, of course not, that's absurd

Edited again to comment Ros #….618 above may be onto something. Of course the more powerful the scope the further back one can see

Your friend is technically right about seeing the image in the past, ignoring the telescope for a moment. You can't really live in the "now," because it takes time for the brain to process information and it takes time to get information from the rest of the body to the brain.
So yeah, technically what you call "now" is not really "now" but some million millisecond in the past.