Tell us more about your cat's experience on leash if it has had it.
i have tried to take my kitty out on a leash but he HATES going outside. everytime i try to let him out he gets all fluffed up and meows in the most pathetic way. my parents have outdoor cats so im used to cats TRYING to escape, but not my little guy. I have never seen a kitty more afraid of the outside!
Wow don't different smells excite him? Mine would surely be led by them anywhere!
i thought that he would enjoy being outside, but that is definitely not the case. He is very much attached to our dog and to us.. I think being outside overwhelms him because he has been in our apartment since he was very very little (he was a rescue). I also think that is why he is so attached to us.

We havent tried taking the dog and the cat out together yet, however. I feel like he might be a little more comfortable if we did that...but that could also be bad if the dog gets excited (as he tends to when he goes out)...

I am hesitant to say that having my boyfriend hold him would help, although it usually does comfort him (he lovessss his dad ;]) like if we go to the vet or something....he would probably just get nervous and try to hide in his armpit. I wish he loved the outdoors because I love being outside and i know he gets lonely when we're gone but I also dont want to stress him out by pushing him too far.