Last week I mentioned getting out of your comfort zone, whatever shape that may take. For some, choosing to spend time out in the world all alone is a radical notion, but I think it’s one of the best things you can do: get to know yourself, one on one. I wrote about it here.

There’s nothing wrong with being a party of one. But if you need someone to talk to, you can always talk to me.

Hey Fifi,

I’ve been sleeping with someone on and off for a couple of years and I’m pretty sure I’ve developed some strong feelings.

The thing is, while we are also incredibly good mates, it’s never escalated into the realms of the romantic. I figure if we were going to date, it’d have happened by now.

So what to do, confess everything and potentially lose a mate and be heartbroken? Take a chance and tell them everything? Is there any way of knowing if they like me as more than a friend with benefits?

He who dares wins. Fortune favours the brave. Grab life by the whatever. For good measure? Shit or get off the pot.

Take your pick. These are all phrases we hear bandied around a lot in life, and the older I get, the more I think that these potentially trite aphorisms are clichés for a reason. They’re frequently just so damn applicable.

First off, let’s disregard the fact it hasn’t happened by now. That’s 50% on you! Unless there’s ironclad evidence to the contrary (like verbal confirmation from them that they want FWB and nothing else) then there’s always the chance they silently feel the same way you do.

Here it is: I think you’ve gotta do it. A risk is run in conjunction with its reward. The potential reward here is big, so it follows that there’s a stomach-churning gamble involved. Be brave. From where I stand, the possibility of a good relationship with someone you fancy and get on with as a mate is worth the risk.

If you were holding a candle with no evidence of it being reciprocated and/or this person had a significant other, I’d be giving you much, much more cautious advice right now. But you’ve slept together on and off for years! That’s about as much of a positive signal as you’re gonna get.

If the carrot doesn’t move you, think of the stick. By which I mean, imagine what might lie ahead – how are you gonna feel when they inevitably couple up with someone for serious and it looks like you missed your window? Honestly, that has the potential to be an even bigger heartbreak than just giving it a good old college try and simply striking out.

There are various approaches to this, of course. Picture a sliding scale that runs the gamut from balls to wall “we need to talk” style confessions right up to subtly dropping hints and hoping they pick up what you’re putting down.

If you’re really shitting a brick about this, maybe try jokey suggestions of dates during pillow talk the next time things are intimate to see how they react. Or simply engineer situations where the two of you have one-on-one time and see how it develops. You don’t have to confess your undying love straight away, rather give yourself opportunities to gauge interest. Either that or just out with it – depends on how brave you’re feeling.

Your friendship withstood the awkwardness of occasionally banging, I think it can withstand the awkwardness of floating the idea of a date. Worst case scenario, they let you down gently, things are a bit awkward but go back to normal with time. It will hurt, but at least you’ll know.

I’m of the mind that knowing how things are for certain, even if it’s not the answer you want, is far preferable to always wondering what could have been. Go with your gut, but give yourself a fighting chance. Good luck!

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Note: This letter edited for clarity – by which I mean I couldn’t in all good conscience keep the original phrase “developed some hardcore feels” used by the letter-writer in my final piece.

Want to talk?

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Confess a story, ask for help or just shout into the void for a bit and see if that helps. All welcome. Anonymity totally guaranteed always. 

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