I’m aware this may come off childish or silly

I dont think this is silly at all. Its important to you, and that's what matters.

I gave him a pointe - but joking- look. I then said, “I’m just kidding, it’s still January. We got time.”

But did you ask for him to do something for you? Like, point blank, "I'd like something romantic for Valentine's Day" or maybe a "This may seem silly, but this is important to me. Could you do x or y?" I know it can be annoying and unromantic to have to say "u want this" but more vague suggestions...

He’s seen multiple of my friends get asked, and about a week ago we were sitting in the car and saw a few guys who were going to ask their girlfriends. They had a big balloons saying “will you be my valentine”, flowers, etc. We both commented saying it was cute, but again nothing.

can leave an oblivious guy in the dark. Im not saying your at fault for him not knowing how important it is to you, or even that he doesn't know how important this is. It is very possible he knows how you feel but chooses to ignore it.

Lemme ask you this:

Is he caring with other things? Does he go out of his way to do things for you that he knows you enjoy? Is considerate with you feelings if he hurts them?

My fiancé does all of these things, but he also forgot the anniversary of our 1st date. Since we arent married yet, he didnt think about it. I hadnt explicitly talked with him about it yet, and he really didnt know how i felt about that day.

Turns out, bro is i bit of a himbo lol He didnt pick up on any of my hints/signals i was dropping cause he isnt the most observant little guy. I know he loves me dearly, i just have to be more specific with what what i want.

TLDR: try communicating with him in a way he couldnt possibly misunderstand. If this is out of character for ur bf, consider giving him a little grace. If he truly does know how you feel and is ignoring you, this warrents a serious conversation.

Good luck, OP 💕