Did Frodo and Gandalf actually meet before Bilbo and Frodo's party?
 

I don't know why I haven't thought of it before, but I was confused after I pondered it (This is one of the things I do before I go to sleep at night, pondering Tolkien). It has been bugging me for some days now and I cannot seem to find the answer.
It appears that Frodo and Gandalf have meet before September of Frodo's 33rd year in the Peter Jackson film because it seems that they have been united after a long absence of each other (well, that's what I always thought). The radio plays give me the same impression. But when I read my books, it does not seem so. It looks as if Frodo has been informed about Gandalf but not actually met Gandalf.

I guess what I am trying to get out (because my thoughts when I get them down on paper (or the screen) seem to be a bit hard to follow) is did Frodo meet Gandalf before the month of Bilbo's 111 party?

Any thoughts?

I do not think so. The way I always viewed it was that Frodo had heard all about Gandalf from Bilbo but never actually met him until the party. I had the same impression with Bilbo meeting Gandalf back in the Hobbit. The way it is written makes it sound like both had heard all about Gandalf, mostly his fireworks and they both met him after hearing all about him.

The hobbit children knew Gandalf by sight so I deem he had been there more than once even during their lifetime. And Frodo had lived at Bag End for about 12 years by the time of The Party so he would definitely have met Gandalf at least couple of times. Maybe their acquaintance deepened into true friendship only after Bilbo's departure and Frodo's coming of age. Knowing Frodo had his rascal period while in his tweens (and earlier; referring to farmer Maggot and his mushrooms :)) I can well imagine what might have happened if Gandalf let his fireworks unguarded:

*KA-BOOOOOM!!*

"Fool of a Baggins!"

Sorry.... :D

Yes, they very surely did, as this quote from the Thain's Book encyclopedia points out:

I'll also try to find a quote in the books that supports the quotation above.

Apparently I was under the wrong impression for quite a while. Now I feel quite stupid.

Did Gandalf ever meet Bilbo prior to their meeting at the beginning of the Hobbit? I think that either Bilbo had met Gandalf once when he (Bilbo) was very young or he had never met Gandalf prior to that meeting. Bilbo talks about Gandalf as if he is someone Bilbo has not seen in years or someone he has heard a lot about but not met yet.

It's possible. Bilbo would have been a child (not a baby) at the time of the Fell Winter, when Gandalf "came to the aid of the Shire folk." I suspect, however, that any meeting that might have occurred would have been brief and comparatively insignificant. At the time of The Hobbit, it's clear that Gandalf had been observing Bilbo for some time (particularly from what I recall of the tale as told by Gandalf in UT). That Bilbo actually remembers the fireworks Gandalf made for the Old Took would mean that there was a possibility that they had met at some time prior to TH, but again, I suspect the meeting would have been casual, at best.

So, more evidence points to Frodo and Gandalf meeting prior to the Party than evidence points to them not meeting it looks like.

In The Quest of Erebor, Unfinished Tales, Gandalf says of Bilbo "I had known him once very well, almost up to his coming of age, better than he had known me". He later goes on to say "I remember how he used to pester with questions when he was a youngster....".

That is interesting. Almost like Gandalf decided to watch over him.

Or was Gandalf MEANT to meet Bilbo. That is way fate seems to work in Middle-earth.

Didn't Gandalf tell the hobbits that him meeting Bilbo and the Dwarves were chance meetings? I don't have my copy of UT with me, so I couldn't find the passage...

No I think Gandalf told the hobbits that his meeting the Dwarfs was a chance meeting and meeting Bilbo was not.

That's correct, his meeting with Thorin Oakenshield was a chance meeting on the edge of spring, not far from Bree. At that point he'd already met Bilbo.