life, the ice cream cone, and everything

Yesterday L. asked if he could go out to eat with a friend "El". I said "Yes, but that he had to stop accepting invitations without reciprocating."  But, it turned out it wasn't really an invitation that one had to reciprocate. I don't know if he didn't want to give me the details or if he didn't really know what was up. L told me he'd be going with El's mom (looked a bit uncertain when he said it) and so, when my husband asked me if we should send L with money, I said not if he was being invited by El's family.

Well, El got to the door and I had managed to dig a dollar out of my wallet and some pennies and dimes because I meant to send L with a little cash in his pocket just in case.
I looked at El and said, "You guys better be treating."
El said he had $6!   
           That is NOT what you say if you have a mother waiting to pick up the tab.
It turns out that El and L are just going to walk over to get ice cream because a certain girl had invited El to do this but had told him she didn't want to go just with him. (Here we have a potentially very amusing story about how long hubby and I speculated about this girl.  I love it that I can give his dad such pride and joy by suggesting that this girl had asked El specifically to get L in on this ice cream social.)
But, back to the main story: 
I was a bit embarrassed to have suggested to El that he should invite my son - but cleverly saved the awkward situation by saying to L, "Go talk to your dad.  He has $5.00." or something like that.  I tried to make it sound like I wasn't backtracking from what I had just said about there only being a dollar and change available for L... he could get more.  You know?  Like I wasn't really being cheap before.
But I'm really not cheap.  And that's where this is leading.  L has had a rough semester academically and, now more than ever, I hate to just shove $$ into his hand.

L went out for ice cream with $6.00 in his pocket.  He came home with one dollar and just a tiny appetite for dinner.
I took $5.00 out of his allowance.  I told him that at times his dad and I would cover these things, but at times he'd have to cover them (and we'd be more inclined to cover them when his grades were good).  That last part irritated him.
I HATE to be inconsistent.  I'd like to say, you need to pay for all of this except under X, Y or Z conditions - something like that.
But, his dad would like to cover these little social outings always - so I don't mention to his dad that the money actually came from his allowance.
Many of you will think I'm evil, but I have had this conversation with my husband.  Trust me, it backfired.  Sigh...
My husband remembers being poor and not being able to invite out any girls because he never had any money.  He wants to spare his son and he takes great pleasure in being able to give his son some of the things he was deprived of  (I mentioned food in another post).
What I can't get him to accept is that his own struggle may have helped shape him in positive ways and that we can try to leave some struggle.  That is, L is never going to suffer the way his father suffered, and I'm just as happy about that as anyone.  But...but if you don't expose your kids to some tough choices, moments in which they have to decide what their priorities are --the nintendo game or the girl--, one is depriving them of something valuable.  Sigh... So, I feel the need to make L see that all these aspects of his life are part of the same ... process.  Damn, becoming very repetitive here - NOT eloquent.
For example, L didn't need to buy the biggest ice cream cone to have fun (at the place they went, $5.00 and change buys a heck of a lot of sugar).  If he eventually understands that this choice may negatively impact other parts of his independence, he'll make different choices.  I don't know if I can really create this situation for L.  Sometimes I worry - No, often I worry.  His father will be over 70 when he graduates from college.  Will we have given him the foundation he needs to go out and make critical decisions about his daily life and his future?
See, that's what this ice cream represents to me... Way too much...