Should I tell my best friend I'm in love with her?

“The stakes are high; strong friendship often lasts a lifetime, long beyond many marriages,” Kenny Mammarella-D’Cruz says (Photo: Nicolas Hansen/Getty)

Dear JS

The million-dollar question: do you tell your friend about your feelings?

Firstly, it’s important you really consider whether you’re in love with your friend. I wonder whether, at some level, she was your first love, emblematic of you becoming independent – she might always make you feel young. Is this love, though, or more a nostalgia for the carefree years at university? It might be useful to consider: if you did have a partner and your friend had recently split up with her boyfriend, would her newly single status be a little more background in your life? Could this partly be because of the situation?

If the answer to these questions is a resounding no, then I completely understand why you’re considering risking your friendship.

If, by making a move, you’re considering pouncing on her, I’d caution you to change tack. Instead – as I would guess you are thinking – I’d encourage you to open a conversation about what you are both looking for in a relationship. Listen to what she says, let her talk about previous partners, and see whether your visions for future relationships are similar. This gives space for you to feel your way and for your friendship to naturally develop – for you both to ask: what might be? It might become very clear that she would be interested in a relationship with you: I’ve been around many relationships which started out as a strong friendship and it’s a gift.

Opening up conversations and giving this a chance to evolve organically might also leave you none the wiser, which is often the case with close friendships. You already know that you care for each other. If that’s the case, disappointingly, I can’t offer you the winning formula for exactly what to do and say. Instead, I’d encourage you to rely on your own instincts. The stakes are high; strong friendship often lasts a lifetime, long beyond many marriages. But love is an emotion that is inherently laced with risk; it makes everyone vulnerable because it’s entwined with eventual loss.

I asked a friend about your dilemma and she saw it as clear-cut: if you’re not brave enough to tell your friend your real feelings and take the risk, then you aren’t brave enough for love, with its highs and lows, passion and boredom and support for each other. She couldn’t understand why you’d miss out on the chance of love, which she says isn’t like catching a bus and doesn’t come around often in life.

I see your caution more as an indicator of how important this friendship is to you and how much you appreciate your friend’s presence in your life. A lot of people start questioning their university friendships in their thirties as their lifestyles evolve, but it seems like yours has remained strong, which often happens when our values align (which is helpful in all types of relationship).

I suggest asking yourself how you’d feel if you didn’t say anything, and, importantly, if you did reveal how you’re feeling and learn that she doesn’t feel similarly. One of those is instinctively likely to feel more disappointing than the other. Another question to consider is: would you choose the love of your life or the friendship of your life?

Friendships thrive on equality: whether that’s a close friend where you both share your innermost feelings or a casual acquaintance who you enjoy catching up with now and again, we’re most comfortable when our level of fondness is, for the most part, similarly matched. It feels awkward if someone wants to spend lots of time with us when we like them at arm’s length. This means that if you do come clean about your feelings, and your friend doesn’t share them, it is likely to shake your friendship, at least at first.

This isn’t to put you off putting your heart on the line: you might feel a sense of relief in being honest and sharing your secret, even if it doesn’t lead to a life together.

While I believe that only you can know what is best here, do keep in mind that your friend might have some catching up to do: while you’ve been in love for a long time she might never have considered you as a potential partner. Give her a chance to consider whether she’d like a relationship with you rather than carrying any expectation that she might already know the answer. Good luck – and please let me know what you decide!