I think you should bring it up. It's not a big deal to you, so you're not going to come off weird. It's likely that he's having the same thoughts, and it's better to just address it directly. "Boyf, what timing lol." I'm not a wait-and-see person, tho, so if you are then take my thoughts with a grain of salt.

oh yeah, you HAVE to discuss this. you can't exist in this state of mutual fear. whatever awkwardness comes from the conversation will be SO MUCH WORSE on the actual day. Even just a frank acknowledgement of "I don't know if we're at the Valentine's phase of this relationship" would be much better than a silent fizzle out.

I say you bring it up! No need to wait for him to start the conversation about Valentine’s Day. I brought it up to my boyfriend (only been dating 2 months btw) and we made a plan together of what we wanted to do. Maybe you can suggest an activity together instead of gifts. 

As someone who LOVES Valentines Day, I will find any and which way to bring it up. I'll be like "I love the color pink, speaking of pink", "I love flowers, speaking of flowers"... I am a nightmare. But when it comes to gifts, I think this is the perfect time for a thoughtful, funny gift. Let him take you to dinner and do all the romantic stuff, you stay cute and give him a shirt. It's what men deserve <3

 I would just give him the tee on Valentine's Day however you were planning on giving it to him bc who doesn't love a gift? Also, the best gifts are thoughtful ones—like your t-shirt—and ones that are given with no expectation of return. If he  doesn't have something for you, I wouldn't sweat it. It's early, and also gives you the opp to talk about V Day and whether it's a holiday you both want to celebrate moving forward. Go with your first instinct (a cute, fun gift!) and don't overthink it.

So many good thoughts on all ends! I agree that the best way is to be in your truth. If you want to do something for Vday or talk about it, bring it up! Then you can go from there as to whether you want to plan something specifically, give the gift, etc. But, since I've never been in a relationship on Valentine's Day, there is also the chance that I might be totally off here lol

I think the relationship is so new and it's so close to Valentines Day...just bring it up!! I think it's less awkward to be like "Hey I know this relationship is new..I don't really want to celebrate Valentines Day" (Or if you do, say so!) I think a little bit of awkwardness now is better than him going over the top and buying some big gift and you're like....here's a shirt?

I think you should bring it up. Because maybe both of you are thinking the same thing you want to get gifts for each other but maybe it’s too early and you both don’t wanna come off as creepy. Dating is hard enough but especially if you found someone in this pandemic to stay with then communication is key. I do like the idea of a gag gift or an inside joke gift.

Lol you are not insane. Something that has worked for me in the past in a similar situation was just saying something along the lines of "I'm so happy I have a valentine this year," or something like that to acknowledge the relationship and holiday to spark the conversation about any plans. Good call getting a sweet and cute lil gift anyway.

Prepare how?  Like mentally brace yourself to be disappointed? Lol.  In these cases, I say make it a joke.  Tell him you’re super excited about the 9 course dinner he has planned w Kardashian level floral displays and a private jet to Fiji.   Or something to break the ice.  Because men  are clueless and he might just need a reminder of some sort that it’s even a thing.

I'm in a new relationship. (We had the DTR talk last week.) We've met each other's friends been on a bunch of dates, genuinely enjoy spending time with the other. The only thing is, neither of us has mentioned Valentine's Day. Now, I'm not a girl who really NEEDS to do something, but I feel like us not even acknowledging it is weird? I know there's still time, and maybe he'll bring it up this weekend, but I want to know how I should prepare. I got him a funny t-shirt as a gift that's an inside joke — nothing too serious, but at least something I can give him if he has something planned? Am I insane? 

We haven't brought up Valentine's Day...