I’m sure you get a lot of this sort of question, but I figured I’d send it anyway. My problem is pretty standard; I have a raging crush on one of my best friends and have for over a year, although he’s been in a relationship for nine months of that, so obviously was off limits until they (sadly) split in the summer.
My problem is that I know I need to talk to him about it – he acts quite flirty, and I’m not sure whether that’s just best-friend behaviour or I’m-interested-in-you-romantically behaviour. We cuddle, he gave me a thread bracelet for good luck when I had a difficult couple of days, we often spend hours talking and completely lose track of the time. My current plan is to, this Christmas, when we’re both back from university, is to get a bit tipsy so if anything goes horrifically wrong I can blame it on the alcohol, but I just have no idea how to initiate this conversation. (I am aware that I’m risking our wonderful and highly-valued friendship, but I’ve got the point where whenever I talk to him I’m getting stupid butterflies-in-my-stomach and squeezy-heart-feelings and I just need to know either way so I can celebrate or move on.) If you have any ideas that would be highly appreciated.
In that case, Sparkler, I’m delighted to inform you that I have many, many ideas as to how you might initiate this conversation! … Although I must confess that at least half those ideas involve a radically complicated, ripped-from-Hollywood scheme wherein you show up to your holiday bar date with a hired actor who you introduce as your fiancé, thus inciting immense jealousy in your crush, which sets off a series of increasingly wild hijinks that ultimately culminates with a department store Santa Claus running pantsless down the street, on fire, whilst you and your beloved share a passionate kiss under the mistletoe. (I must also confess that I may or may not have completely lost my grip on reality after watching one too many Hallmark Channel holiday movies this week.)
But even once we’ve eliminated from the running any/all options that could double as the plot of a terrible Christmas movie (working title: Love Um Actually Not), there are still plenty of ways to spark the convo that leads to a crush confession — including the one you’ve already written down! If you’re brave enough to say it out loud, you’d be hard-pressed to find a better conversation-starter than “I am aware that I’m risking our wonderful and highly-valued friendship by saying this, but I’ve got squeezy-heart-feelings for you — and I’d like to know if they’re reciprocated so I can either celebrate or move on.”
And if you’d rather not take such a huge leap, then there’s always the tried-and-true loaded question. If you ask him, “Soooo, are you interested in anyone?”, you open the door to a conversation that gives you salient information either way but also gives him an opening to confess his feelings, if he has them. Or say, “Have you ever thought about what it would be like if we dated?” and see how he reacts. (Best-case scenario: he’s like “OMG ALL THE TIME”, and then you make out; worst-case scenario, he laughs so hard that eggnog comes out his nose, and you’re all HAHAHA YES I WAS JUST KIDDING HA HAAAAAA, and then you go home and put on your coziest Christmas pajamas and congratulate yourself on how smoothly you saved face… even if you then cry yourself to sleep while eating an entire gingerbread house.)
Whatever your approach ends up being, though, you’ve already made the most important decision: to be brave and honest about your feelings, and to hope for the best, even as you prepare yourself to be gracious if you don’t get your hoped-for outcome. And that’s an amazing thing, because when you’re coming at this situation with so much maturity, confidence, and courage, you just don’t have to worry if you’re not super-duper suave about it. You don’t need the perfect opening line when your heart is in the right place. And with a little luck, you may find that you never even have to say a word — simply because the combination of a dimly-lit bar plus the magic of Christmas plus your apparent chemistry with this guy could shove your relationship into romantic smoochy territory, without either of you ever saying a word. It’s been known to happen! Let us know how it goes!
And to you — and to all — may your holidays be happy, may your hams be perfectly seasoned, and may all your department store Santas be fully and properly clothed.
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