[Saddlepoint]

This is a very tricky and interesting situation.

I lean towards leading an amount where he isn't committed when you push over his raise. And then, you know, push over his raise. If he likes to overbet, that might mean half the pot. You have nine and a half outs at least and maybe more if he hasn't paired, so you shouldn't be afraid of getting all your chips in as long as you leave him room to fold.

The other obvious line would be checking with the intention of calling or raising, but I don't like this for a few reasons. It could let him to shut you out with an overbet, and, if you check/raise, risks you getting shut out by a push. My favorite line is the one I mentioned above, and my second favorite is check/folding. Play your big pots against this guy when you're in position.

As for pre-flop: calling here isn't bad, but neither is folding. You have position on this guy at the table. That's going to be invaluable. So let him steal your blinds a lot, so you don't end up playing lots of pots oop.

PS - Why did you post this in small stakes?