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Dear Kaelyn…


Written by Kaelyn Spickler

Dear Kaelyn,

I’ve been talking to this boy since the first week back from break. Obviously that’s only been a couple of weeks at this point, but we’ve gone on about four or five dates, and we see each other most days of the week. Basically, I really like him! But, what do I do about Valentine’s Day coming up? Is it expected we do something or is it too soon?

-Valentine’s Day Freak Out, ‘21

This is a tough one for sure- been there, done that, and I still don’t think I can give you a solidified answer. Of course, the obvious answer is to just ask him, but I know you don’t want to hear that because if it were that easy, then this wouldn’t be a big deal! My advice is to feel out the situation a little bit. Is this guy a romantic or is he more low-key? Sometimes you can tell just by how he treats you, the dates you all have gone on, and the kind of guy he is. Pay close attention to any mention of Valentine’s Day, too. That can be your biggest hint. 

If you’re thinking he may be planning something or getting you something, a good way to play it safe in the beginning is to do something thoughtful but also light-hearted. Have you noticed that he said he needs a new phone case or dropped the name of his favorite candy or food? Getting things like this may seem easy, but in the beginning, it shows that you’ve been paying attention which gives you bonus points. 

I think it’s also fun to get a box of little Valentine’s Day cards, use some for your friends, and then save a couple for him and write puns on them like “you’re a fine-apple.” That’s something cute but also super low-key. 

If you really are worried about this, though, it doesn’t hurt to just ask. You can keep the tone relaxed by simply saying, “So, Valentine’s Day is in a week, and I’m just wondering if we are at the stage where we do even a little something.” This opens the door for further conversation that may also give you clarity on where you stand with him and where he sees this going. 

If all else fails, you can get him something you think he’d like, wrap it up, hide it in your room somewhere, and if you end up celebrating Valentine’s Day, then you are set, and if not, you can just take it back and pretend like it didn’t happen.