I will be blunt here.You are expecting dinner from a guy who is asking money for gas from his dad.Wake up ! he cant afford it.he doesnt have a job,he is broke! This is such an unrealistic demand from your side.it is very insensitive as well.Why dont you offer taking him to dinner? or go dutch? you cant expect him to sell his house just because you want a dinner.This is absurd.Why I am replaying here is absurd in itself...

I agree with heissick. If taking you out to dinner and paying for things for you is of any importance, find a man with a job. You're barking up the wrong tree, and I don't think you have any right to get upset when you choose to start dating (online dating with Match.com) a guy who was broke and jobless from the beginning. You don't know why he would take you to dinner but you know he's broke - Why aren't you putting two and two together? He doesn't want to pay for you because he can't...

Thanks, but both of you didn't get the point of this post....

My question was, what should I do since he left the dinner date using Match.com up to me? He said whenever I wanted to go to let him know, but I don't feel comfortable doing that...

They did get the point. The whole issue is that your guy has no job and no money. You want a dinner date using Match.com but your conscience says you know that him having to take money from his father to pay would be wrong. Its a stalemate.He cannot afford to go out thus you dont tell him you want to go. My opinion is either dont go out as you know he cannot afford it, go out and know he is getting being lent money he cannot afford to repay or move on and find a man with a job so that when he does take you out, you wont feel guilty.Good luckSB.

Que Sera Sera - Whatever will be, will be...

Is he actively looking for a job?  If not, then he may be dud..

Otherwise .. he could easily prepare you dinner.  I'm sure he's feeding himself dinner everynight from groceries bought at the store .. he could add a cutlet or two and not break the bank...

Just a thought. Maybe he "left it up to you" to decide dinner because he KNOWS you wouldn't feel comfortable calling him up and asking to go out.  I don't know many people who would feel comfortable calling up someone else asking them to buy them dinner.  Clearly he is broke. If he could afford to take you out, he probably would have by now (more then once).  Maybe he left it up to you because he didn't want to feel like a jerk for never taking you out. So he made it appear that he would do it "whenever you want", without committing to it.  I mean if you ever got frustrated and said "You never even take me out to dinner!" I think his response may be along the lines of "I told you I would take you out whenever, just to let me know! YOU never told me when you wanted to go!"  So it keeps the "heat" (or guilt) off of him for not taking you to dinner. He doesn't want to initiate because he CAN'T afford it. He is banking on you not initiating either. At least thats my best guess...