Your question was: Should I tell him tonight?.

HEY GIRL...UNLESS HE IS A DUMB TEACHER, HE DID NOT TELL YOU THAT HE HAS PLANS WITH SOMEONE ELSE TO GIVE YOU THE IDEA THAT HE FEELS THE SAME WAY YOU DO. I BELIEVE THAT HE IS NOT TOTALLY CLUELESS ABOUT Y0UR FEELINGS. BE CAUTIOUS AND IF THINGS DON'T SEEM TO BE GOING IN THE DIRECTION YOU WOULD LIKE, THEN DON'T SPEND TOO MUCH TIME ON IT, THERE ARE TOO MANY FISH IN THE SEA. DO NOT TELL HIM ABOUT YOUR FEELINGS, IT JUST MIGHT COMPLICATE THINGS. UNLESS YOU ARE ABSOLUTELY SURE THAT HE IS NOT SEEING SOMEONE ALREADY...

If this person he's meeting on saturday is actually a "date", then it's brand new. I know he's been single for several months. I don't think I'm going to tell all later like I thought I was going to. I still am not sure what I think is the best thing to do yet though...

Hon, if he were interested, he would have let you know.  I wouldn't go pouring out your feelings for him.  If you are going to keep seeing him socially, then you can do things to let him know that you're interested.  If he's interested, he'll ask you out.  He might have his own rules against dating (online dating with Match.com) students whether they are in his classes or not so don't risk making things awkward.  If he wants to date using Match.com you, he'll ask you out.

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This might be reaching you too late this evening but, you can discreetly find out from him if this person is a date using Match.com or a girlfriend by asking how the dinner went after the fact. Kind of like, "So, did you and your date? girlfriend? enjoy your evening?" Then he will clarify things for you. If you are determined to date using Match.com him, then you can, in a playful like way make sure that he knows that you think he's attractive or a good catch or whatever term you like to use when you describe men and she is a lucky girl because if he wasn't dating (online dating with Match.com) someone you'd want to date using Match.com him yourself. If it is done with confidence and a smile and playfulness you will not humiliate yourself. And it sends a definitive message to him that if things dont work out with this girl that you would like to date using Match.com him. After that, I wouldn't try to interfere with any relationship (thru Match.com) he is in with another woman. I would let it go at that otherwise you could look desperate...

Just ask him to join you to something casually at some point or for coffee or a bite - is there something you can ask him to help you with - i.e. putting up shelves, sharing his knowledge about his area of expertise?  Guy really liked to be asked for help and you're putting it out there that he is someone whose company you enjoy in  low pressure kind of way.

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