The question I’ve known one of my best friends for more than 20 years. There has been nothing but friendship in those years. We have common interests and hobbies, I’m called uncle by her children, and we socialise frequently. Over the past year I have developed feelings beyond friendship towards her. However, due to our existing bond, I’m unsure how to approach the situation. I’ve been single for some years and happy with that. I also do not want to jeopardise our current relationship and certainly do not want to lose her as a friend. She has recently ended a long-term relationship and has started exploring dating again. We have various social engagements, both with friends and alone, planned in the coming months. I know I should address my feelings for her, but I cannot see a safe way to start the discussion without threatening our current stable friendship.
Philippa’s answer I don’t think there is such a thing as a safe way to start this discussion with her. First, take some more time to explore and understand your own feelings. Consider whether these feelings are fleeting or if they hold deeper significance.
Maybe the following questions will help you become clearer: why haven’t you been in love with her before? Why only in the past year? Apart from her becoming single, has anything happened in your life recently that has precipitated this change of heart of yours? Do you think you have been in love with her for a long time, but didn’t dare admit it to yourself until she was single? Can you think of what specifically you would want from a romantic relationship with her? Is part of what is fuelling your romantic inclination towards her that you are unsure of how she feels? And if so, is this jeopardy fuelling erotic feelings towards her? Do you just admire, respect and love her, or are your feelings perhaps tinged with jealousy influenced by her now being on the dating scene?
Usually before we reveal how we feel about someone, we get a sense of how they feel about us, which may give us clues as to whether we are being appropriate or not. Look at what signals you are getting from her. And what signals you are giving out. Are you smiling at each other more? Does she reach out to touch your arm? Do you lean in together when in conversation? Is she seeking out more opportunities to spend time with you than she did before? Are you both sharing more intimate details about your lives now? Is she at all put out when other people claim your time and attention? Do you stay in eye contact longer than you used to? Usually there is unspoken communication like this that helps pave the way for verbal communication. These signs are not gospel, but interactions that happen wordlessly may just give you an inkling of how she feels about you. We all have different levels of sensitivity when it comes to picking up on wordless, unconscious signals from others and, however sensitive we may be, our perception may still be wrong.
Now, suppose having considered your own feelings and motivations deeply and perhaps had a bit of an idea about how she might feel, you still feel you want to declare your feelings for her – how are you going to do that?
First, try not to be over-invested in a favourable outcome. Second, my advice would be to try to keep it light because then, if she doesn’t reciprocate, it would be less awkward to get back to where you were. Tell her you don’t have any expectation of her feeling the same, it could be that you’ve watched too many romcoms, but you have romantic feelings for her that you are declaring on the improbable off chance that she could feel similarly. That would be my style, I don’t know what yours is, but whatever it is, don’t deviate from it too far. It might be more natural for you to say, if it were true, something like, I’m surprised to find I’m jealous of the dates you are going on because I want to take you on a date.
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However you declare it, tell her the truth of how conflicted you feel about saying it, say this because her friendship is so important to you, and you’d hate to jeopardise it.
Hope for the best, but be prepared for the worst. If your romantic feelings are not reciprocated, think about what you could say or do to help your existing relationship together. Your friend may need space and time to consider what you’ve said; give her as much as she needs.
She is one of your best friends, maybe the sort of friend that you would lean on to debrief after taking such a brave step as you are considering. You need such a friend to talk to about how you are feeling at the moment, too.
There is no such thing as a risk-free way to go about this, but if you don’t do it, you may have regrets you subsequently find hard to live with, as you very well might even if you do. I’m sure every reader will be rooting for you, as I am.
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