I’ve been dating this guy  for almost 3 months, and things are going well. Last night it was his birthday and planned something for us which he really appreciated and we had an awesome time. We kissed goodbye at the subway station and he held my hands and said he would see me when he gets back (he is going on a trip and coming back Mon. morning) and then we kissed again and he said “see you next week” and saw me off to my train. We sometimes make plans for a specific day for the next date, but not if one of us is traveling or we’re really busy, etc.
However – Tuesday is Valentine’s day, and I know that’s not even a real holiday, but I’ve never been dating someone during V day and think it would be kind of nice to do something. But I don’t know how to approach this. He’s flying out tonight and will be busy all weekend until he flies back Monday morning. So I could just wait until Monday to see if he asks me about V day but at the same time I don’t want it to see like I’m just sitting here waiting for him to ask when he probably won’t have time to think about it until Monday. Should I ask him or just leave it?
There really is nothing like the anxiety around Valentine’s Day when you aren’t seriously dating someone, is there? The expectations aren’t clear, and because the day comes with so much baggage, it can be easy to get a little uncomfortable with the whole day. But let’s not dive in to the vagaries of hypothetical people’s situations, let’s talk about your situation.
I think, in your case, waiting would be a waste of time. I’m not saying that you need to ask him on a date and plan everything, but I think that given your situation, it would be perfectly okay to ask if he wants to do something on Valentine’s Day. You’ve been dating for 3 months, which isn’t the longest amount of time, but it’s not exactly like a short amount of time either. More importantly, you spent his birthday with him. That’s a pretty big milestone, more so than Valentine’s Day, in my opinion. All those things alone are great justifications to just come out and ask if he’d like to do something on Valentine’s Day.
More than that, do it because you want to. You’ve never dated someone during Valentine’s Day and the fact that you’re even asking means that the day holds some significance to you. Whatever is stopping you from asking, whether it’s gender roles, or not wanting to come on too strong, or who knows what else, just let it go. It’s better to ask and get a no, then wonder why you didn’t get asked on a date and what that might mean. There’s nothing wrong with asking someone you’ve been dating for a couple of months if they want to do something for Valentine’s Day, or any day, regardless of who society tells you should normally take the lead on these sort of things. The worst thing that can happen is that you get a no. Maybe you’ll get a yes and finally get that V-Day date you’ve always wanted.
Good Luck Out There.