Matchmaking: Dangerous road

I get the art of matchmaking, and I get that in this single world you need a friend to help you play "wingman" every once in a while.  Here's my thing, and this happened recently:

A friend of mine and I went out to dinner to a swanky place the other night, and he originally told me he wasn't interested in our young waitress, that I should stop asking about his pursuit of a friend of his (who I thought would make a great match for him, but apparently from what I'm picking up, she's a bit rude with him), etc.  So I didn't pursue anything in regards to any of that.  He and I had a great dinner, and all that jazz.

Then I find out he's interested in our waitress, wants to hit on her while we're at dinner, and while I'm trying to work some business with her and the event staff (long story).  I told him "NO!" to not even go there in my presence, that if he wanted to approach that at a later time, he was going to do it without me present. I was trying to conduct business and he was trying to work a little love connection in the mix..... BAD MIX.

The flaws of this theory:

1) I'm working business, you don't get in the middle of my conducting business.  It's rude to me, and it also distracts the staff from actually doing their job. 

2) If they are on the clock, they need to be making money for the company, not trying to get a hook up.  If I saw a staffer of mine trying to make a love connection on the clock, I would have a reprimand for them too.  They need to stay focused on their job.

3) If you haven't taken any advice I have dished out in the last few months, including requesting that you read an etiquette book, get a handkerchief for your running nose, and fix some personal hygiene issues, there's NO way I'm going to introduce you to a network of mine.

4) If I get shot down a few times, I'm not going to bother again.  I tried to encourage him to ask this beautiful girl out who was from a similar culture, and he couldn't get the nerve up, and when he did make an appearance, there was some seriously crossed messages from both sides.  I've also encouraged him to get connected with girls at the networking parties he goes to, and singles events.  Not to mention, he wants to date within a very specific culture range, and I don't have any single friends in that culture.  He needs to get a group of friends in that culture that provides that outlet.

There's just some seriously mixed messages coming from this friend, and there is no way I'm going near attempting to set him up again after he's thrown my suggestions to the wind.  There are some basics I've mentioned that he absolutely has to fix and he gets rather defensive about it all.

Should I set the friend up again? No. 

Should I attempt to help him flirt with my regular server? No.

Should I buy him a handkerchief collection? Maybe.

Should I buy him the etiquette book I recommended in April?  No, he's had enough time to buy that.

If you don't want my help in the small things, don't ask me for help in the big stuff.  I bow the hell out of it all.