God dammit. This day somehow fucks with me every single year. Here's this year's dilemma:

Started seeing a new girl last week and things are going pretty smoothly so far, although we haven't fucked yet (which is my own choice). So obviously, things are kind of fresh and I want to hear everyone's opinion on doing something with her on Valentine's Day. There's an awesome place to go for wine tasting in my area, and they're doing some event on Valentine's Day that seems like fun to me. She just moved to the area and doesn't know many people yet, and for as sweet as she is I'd feel like a complete asshole if I abandoned her on the day that women care so much about. Plus, I'm pretty sure that skipping the holiday entirely would give her the wrong message and she'll think I'm not interested at all. The thing is, I don't want to come across as having singled that day out like a complete try-hard who is doing it only to please her, and scare her away as if I'm trying to rush things or whatever.

Also, no need to tell me I have one-itis, I'm overthinking it, or anything like that. I already know. I fucking know.

well if you are right about your gutfeeling that she is sort of expecting you to do something with her on that day, well then just do it simply dont mention the "valentines day" aspect and make it a day like any other day, make it a date like any other date with no extra significance..

Well, I don't really have a gut feeling one way or another. I just know that she'd most likely spend the night alone otherwise.

well, then ask her out the day before and just make it any other date without reference to valentines day, make it something completely ordinary/banal, nothing fancy or v-day related. this why you wont feel like an asshole, she cant give u the asshole card and its just another date- everyone wins. asking her the day b4 doesnt make it appear like u planned something and also increases the chance that she will have other plans anyway.

This is more about your insecurities than about doing anything for her.

I'm more curious about your process rather than what you do for her. Lotta cognitive dissonance (want to win her over vs. want to not appear needy).

This is all about the energy you're doing things through. If its coming out of neediness, while it may not show on V day, it will eventually come out. If its coming out of "I like this chick a lot, and that's cool and totally normal", than your actions won't have any air of neediness and if she believe you are being needy that's more telling of where she's at in life than you.