Sometimes you have to break a promise to get your happy ending.

Most women have them — a handful of girl friends whom they would trust with their lives, and for whom they would go the distance. There are incontrovertible rules that are attached to these friendships: Thou shalt not spill any of these girls’ secrets. Thou shalt not steal any of these girls’ boyfriends. Thou shalt not ditch these girls at a lame party. These tenets are at the heart of female friendship, and if broken, the friendship breaks simultaneously.

The trouble with rules and guidelines is that they often come with exceptions and grey areas. The old adage “Rules are meant to be broken” is always lurking to bite one in the ass. The question then becomes is there a point when you have to do what is right for yourself, and let the friendship chips fall where they may?

Having been nose deep in this quagmire and able to return to retell my tale, perhaps my own history may help clarify the issue.

Windows down, hair whipping in the wind, jelly from a day lounging on the beach, Jessie and I were driving along the coast heading back to the hotel we both worked at for the summer. She played me a voicemail he had left her. Friendly, funny, flirty. He lived in Toronto, while she lived in B.C. now. They had known each other for years. She could see the boathouse of his cottage from the dock of hers.

“When I come and see you in Toronto I will introduce you. You would like each other — he went to OCAD too. Just don’t sleep with him, okay?”

I do not go after men my friends are involved with — I am against the concept. This time, however, there was just something about that voice on the phone. It was warm and kind with the sort of edge I had always been felled by. And so I knew when she said that, I would end up breaking the promise if I made it.

Three months later Jessie came to Toronto, swinging through on her way to see her parents in Kingston. She stayed with me and we hit some bars. Somewhere between the third and the fifth, she called him. He came to meet us.

I could say all of the clichéd things imaginable about that evening. Butterflies? Check. Electricity? Check. Though he is older than me — significantly older — I had consistently dated older men and I wasn’t worried about what anyone would think. I was only worried about the echo of that first request from Jessie, sensing that, as I suspected, it would be impossible to oblige.

The night ended. We exchanged numbers with the intention of being friends. Jessie left for Kingston. They, too, were simply friends. He and I were both interested but reluctant to get too involved. After three months or so I popped by his loft for a cup of tea. All I remember about that afternoon is feeling at home, at home with him in a way that was, in all honesty, slightly unnerving. Afterwards, he drove me near the restaurant where I was meeting friends for dinner. He pulled over and we leaned in to kiss goodbye. That kiss was more than friendly. I almost bolted from the car, hands shaking, until he grabbed me by the arm.

“Whoa – okay. I guess we both need a deep breath after that one. Just stay for a second.”

I was astonished and suddenly calmed. Rather than behaving like other men and bolting (or at least being relieved to see me bolt) at the first sign of intensity, he seemed to genuinely want to take a minute together to clear our heads.

He kissed me again. We said our goodbyes and when I closed the car door I knew that something had just shifted.

There is more: the dating, first in secret, the telling people, and the fall out. In almost five years we have been through long-distance (a year I spent in Florence), short-distance (the subsequent years spent in a loft that was definitely not built for two) and everything in between. Needless to say I was right when I had the feeling I wouldn’t keep that promise to Jessie — five years down the road, I just never imagined how right.

Now, I am not suggesting that all is fair in love and war. Almost everything about both is unfair. I also don’t think my (or his) actions were blameless. The girlfriend tenets and guidelines are there for good reason. The hitch comes when the prudent responsible choice just feels wrong. And so I begin this advice(ish?) column by giving the most common advice in the book. Listen to your gut. Be it getting together or breaking up, the nearly infallible gut should be consulted unilaterally when making decisions of the heart. The gut can surprise you — even when all is good on paper, or your quivering loins are suggesting a smutty course of action, the gut is where your final decision should rest.

We have all looked back after a romantic disaster and isolated that moment that could have saved us, when the gut was lurching, growling or humming with contentment. In my case, it was telling me something I didn’t really want to hear: I didn’t want to hurt my friend, didn’t want to be in a relationship, and certainly didn’t want to face the judgments of friends/family/perfect strangers over our age difference. But the gut knew better. It told me there was something important there, even before we had met, even after I had tried to bolt and avoid the issues altogether. The gut is smarter than me, and for that I am grateful. I am betting yours is too.