I really like this girl in my college, but I know she’s got a boyfriend. I realise that I can’t ask her to break up with him and therefore am not expecting great result, but I really want to tell her how I feel, especially since Valentine’s Day is coming up. Am I out of my mind for wanting to do this?

We all know that Valentine’s Day gets a lot of bad press. Only over the past week, I have heard it described as “capitalist and dehumanising,” “intensifying the loneliness of being single,” and “really annoying.” I’m not going to defend the institution per se, but it seems here that maybe it’s providing the encouragement you need to take the plunge.

It might feel like you’re taking a huge, gargantuan risk: a potentially highly embarrassing, might-as-well-just-join-the-mathletes-and-confirm-social-suicide kind of risk. The prospect of cold hard rejection is obviously not a particularly exciting one, and you do have to face up to the fact that she might just say “thanks, but no thanks” (or hopefully something slightly less brutal). 

Nevertheless, I think there are several reasons why telling her how you feel could be a really good thing. Maybe she likes you too. You don’t seem hopeful of a positive outcome, but it’s certainly a possibility, and not one you should rule out at this stage.

If she says no, there’s no getting away from the fact that it will hurt, but at least you’ll know how she feels, and will, in time, be able to move on. If you left it unsaid, the possibility that she might like you would still weigh on your mind; therefore, at least this way you’ll get a definitive answer.

Still, there are a few issues to address. First of all, I’d make sure any declaration is done on the down low.  I mean, not too quiet. Definitely be audible. I just don’t think this is a time for grand gestures or a cappella bands – you have to be sensitive to the continued presence of the boyfriend, who might not receive the rose bouquet with the same sense of gratitude. Equally, stealth will substantially lessen your chances of incredibly public humiliation. A low-key, private conversation is ideal.

Prior to this declaration of love, you must also carefully consider your relationship with the boyfriend.  Are you friends? Even if you aren’t, he might not step back and happily accept this situation – especially if she changes to your side – making you the relationship-crashing Owen Wilson to his neurotically aggressive Bradley Cooper. I’m just saying, watch out.

Most importantly, if you do this I think you should make sure she knows you’re not expecting anything from her. There’s nothing more unattractive than feeling like someone is trying to press gang you into liking them. Letting her know that you don’t expect her to immediately end her relationship but that you just felt you had to tell her how you feel is far more likely to endear you to her than an aggressive “here’s all the reasons we should be together” speech.

All you’re doing is calmly letting her know she has options. And who knows? Maybe they’re options she’ll consider.