Should I be worried??

Accidentally slipped holding drill and drilled into radiator (yeah hahah) but it didn't leak after a quick drive. Does it look bad enough to replace or will it be ok? I just don't want it to be an issue on a long trip or in the middle of nowhere.

 

If it's just mangled fins, no issue.

 

If your luck is better then mine you will be fine!!

In the second picture you can see that you did some damage to the tube .

Now being this is Aluminum you should at least keep a eye on it will the vibration cause it to crack who knows .

 

Radiators are cheap. Seen some threads about 4.0's dying quick from radiator leaks.

 

Radiator or AC condenser? Sorry can't tell from pic and I used to think the ac compressor was the radiator. Wanted to confirm that before you spent any money, but yeah the fins aren't going to cause you to leak coolant and the tube didn't look too too bad - still a good idea to keep an eye on it and check periodically for leaks.

 

I replaced my stock radiator with a denso a couple weeks ago and it was a fairly simple process. Gear wrenches/1/4" drive sockets make it a much easier process. I would monitor it to see if it begins to leak and replace if needed.

 

I think I'd be inclined to replace it. Although if you only take your truck around town and NEVER drive to the middle of no where you might be able to leave it. It kinda depends on how much you can tolerate being stranded.