The old \'limp-reraise\', hey?!
If he is any good, you need to know what his perception of you is. If he thinks you are tight, he will put you on a big pair for sure. If you have splashed around with him, he might not need to flop big to give you action.
I dont really like the limp reraise move unless its a big reraise. I think you give away your hand, or your hand range, too cheaply here, assuming you play tight. He's only got to call $9.50 more to get a shot at the pot and your remaining stack, and he has position.
I think a limp-call is better here. Play passively and he will probably bet all the way for you.
Obviously, its not gonna work every time, but here I would be happy to call 2 pot-sized bets. If he fires a 3rd, you then have to go with your hand- and player-reading skills.
On this board, playing the way i recommend, you would probably safely fold the river if he fires a third barrel.
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