We can all agree that “I hope we can still be friends” is the biggest BS kiss-off that can emerge from a breakup conversation. The whole thing feels like an urban legend of sorts. So few of us are able to manage being friends with an ex without it ending badly—and why is it even a goal? When looking at the sitch from a distance, it seems obvious that the whole endeavor is masochistic in nature because well-intentioned boundaries quickly give way to broken ones. In fact, research shows people who want to stay friends with their ex and bona fide psychopaths are known to share some similar dark traits. So call me a psychopath, because though most of my attempts at befriending an ex have ended with some ill-fated trips to bedroom and/or vile, misogynistic Facebook messages, I keep on keeping on.

Among the dozen or so ex-whatevers I’ve had over the years, there’s at least one sweet goth boy with whom I am down to share text memes and a coffee. And that’s enough evidence to sell me on the whole masochistic runaround maybe being worth the struggle. After all, occasionally you earnestly care for someone, but being with them in a romantic relationship isn’t the right move. Or maybe enough time has passed to heal your emotional wounds. Or maybe you share a family or your lives are otherwise permanently enmeshed. In these cases and many others, friendship might be plausible (with a lower case “p.”)

But before you veer onto that treacherous road less traveled, you brave, brave soul, reference the three-step checklist below from relationship expert Susan Winter. It asks you to audit the situation, your ex, and how you, yourself, feel about the whole thing, because you owe it to yourself to do some introspection before saying “I do” to friendship with an ex.

1. What did your relationship look like?

Believe it or not, I haven’t been in contact post-split with my former fling who spelled my name as “Marry.” Even at age 19, when I hadn’t yet toned my judgment muscles, that was a real low for me. But I wasn’t looking for a soul mate; I was looking for convenient, rebound sex. And rebound sex guy really isn’t someone who I need in my life anymore, even as a friend.

It make sense that a relationship built solely upon physicality rather than emotional intimacy won’t lead to you to wearing matching Best Friends Forever heart necklaces. Same goes for someone who loved you but didn’t really seem to like you. Big difference. Huge.

“Ex-lovers can also become friends if they truly liked each other as individuals, separate and apart from their romantic connection.” —Susan Winter, relationship expert

“Ex-lovers can also become friends if they truly liked each other as individuals, separate and apart from their romantic connection,” Winter says. So, if you end on friendly terms, you might a prime candidate for testing those platonic waters.

2. Did you, like, just break up?

If you broke up recently, pump the breaks, honey. Take a sec to process the shift before even recognizing that “being friends” is an option on the table.

“Let time pass before grabbing for the friendship card,” Winter says. “Uncoupling is a process that takes time, and learning to see your former lover with new eyes is an adjustment. Time allows the sexual attraction to die down and guarantee that the reasons for your friendship are valid.”

So when someone asks, “can we still be friends?” refrain from immediately plugging a Froyo get-together into your Google calendar. No need to lose faith in the entire concept of friendship between exes, but do prioritize being a friend to yourself first.

3. And why is it that you want to be friends?

Last time my friend got dumped, her ex’s parting words were, “We can still hang out. I don’t really have any friends here.” And wow, did she feel…not special in any way, shape or form. It’s always important to analyze why somebody wants to keep you in their life after the romantic union dissolves. In my friend’s case, it was because the dumper was desperate, lonely, and obviously lacked some finesse in the communication department that might have been barring him from making the friends he was lacking. But, in other cases, it might be that you’re just not over it.

“True friendship with an ex can only happen after both individuals are clearly through the breakup phase, and no longer yearn for each other romantically,” Winter says. Science even backs this one up. An analysis of two studies investigating motives behind a post-breakup friendship found when unresolved romantic issues is the reason for staying chummy, negative emotions—like jealousy, depression, or heartbreak—are a likely result. Alternatively, staying friends for reasons like security and practicality, like if you share assets or a family or simply just like each other as people, correlated with positive outcomes.

“If one partner seeks the sanctity of friendship as a means of ‘getting back with their ex,’ then “friendship” is a ploy—and not a possibility,” Winter says. So do an audit of your emotional stance on your relationship, but also don’t forget to analyze the motivations of your ex. Because in any relationship, romantic or otherwise, it takes two to tango.

Once more for the people in the back, here’s the skinny on whether it’s healthy period to stay friends with an ex. And while we’re talking sticky situations, here’s how to proceed when you want to date your friend’s ex.