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Say what you will about the universe, but never say it doesn’t have a sense of humor.

Almost three years ago, I wrote an Elephant Journal piece where I denigrated the whole idea of “friends with benefits.” Months later, I was involved in exactly that type of relationship.

What wasn’t terribly funny about it was that, inevitably, I lived out the very warnings I originally gave: one of us became emotionally involved and scared the other one enough to put the kibosh on the whole affair. Feelings were hurt. Mean things were said. Profiles were blocked.

I journal quite a bit, so much of what took place was documented in my own marble composition books. Recently, before work one day, I picked up a random notebook and found the entries that referred to this period in my life. While it’s true that the most human thing in the world is to think we could make a failed thing work if we could go back in time and change a few details, I will be the first to say that I am still human.

So with the advantage of hindsight and a dozen humorous notebook entries, I can easily ascertain where the problem spots hide with this sort of arrangement and how you can go about avoiding them. Consider this article a primer on making the impossible—well, possible.

I am an optimist. I am an old dog who never stops trying to learn new tricks. I now believe that with the right people, the right circumstances, and the right ground rules, “friends with benefits” can work.

The five cardinal rules of how not to screw it up are:

1. Be Honest with Yourself. And for God’s sake, confide in a close friend. Sometimes the thought of bedding down with a particular person seems so appetizing that we can talk ourselves into taking on a situation that isn’t good for us. A close friend will usually tell us, in all honesty, whether they think we possess the kind of emotional maturity for a no-strings-attached sexual relationship with a friend or whether we don’t. And while you may not follow this friend’s advice, at least you’ll be prepared for the awful feelings you’re going to have when it all falls apart. Seriously though, it may be a light and easy kind of tryst, but it should be considered with the gravity it deserves.

2. Make Sure you’re Actually Friends. There’s a reason why the expression “Facebook friends with benefits” never quite got off the ground. It’s synonymous with “perfect strangers with benefits.” It makes no sense. When you peel away all of the window dressing, that’s just a one night stand that happens once a week for three months. Unless there is true friendship, with real “friend love,” the friends with benefits option is off the table. I’m not saying it can’t be done, but it’s just not friends with benefits.

3. Common Sense is Crucial. Let’s review, shall we? You and your best friend’s recent ex are sitting at the bar and the sex jokes are making your little wheels spin? Let them spin. This is not a good candidate. The cute guy from the office who looks a little like Matthew McConaughey? Probably not. The guy you’ve known since 10th grade who you always get a coffee with at the Farmer’s Market? Now, you’ve got something! Common sense requires a lot of “playing the tape to the end.” That means, when this ends, which—let’s face it—99.9 percent of affairs do, what will the fallout look like?

4. Don’t Send Mixed Signals. When my FWB thang blew up a few years ago, my person spent 45 minutes on the phone with me giving me an endless litany of everything I did that caused her to want to change the arrangement. It was overwhelming. That phone call, besides being awkward, taught me a few things, though. The first thing she mentioned was that I texted her most mornings to say, “Hi.” I guess I should’ve known that this might’ve made her feel like we were growing into a romantic relationship, but I was clueless. Also, spooning and pillow talk, while beautiful and essential in a conventional relationship, should be avoided at all cost with FWB. The whole idea is supposed to be physical release with a friend—adding those elements confuses everyone.

5. Only Planes run on Autopilot. Contrary to some of the more foolhardy memes I’ve seen on Instagram, there are few instances when relationships can exist without checking in every so often—and this goes doubly for FWB. Chalk it up to the fragile nature of this kind of relationship, but you need to bring it all out in the open every week or so. Is somebody catching feelings? Is someone starting to get serious with someone else? These are all things that are better faced early than late. This one I can’t stress enough. Had I known to do this a few years ago, I probably could’ve saved myself an uncomfortable parting.

Sex is a basic human need, but we can all agree that some breakups and life events leave us unable or just not willing to take on the emotional labor that comes with a full-blown romantic and monogamous relationship. If you can get a handle on these five rules, and your hands on a willing participant, you can have your cake and eat it too.

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