Vice City Pillow Talk: Can You Really Be Friends With an Ex?

My last column was about the tyranny of out-of-the-blue texts from exes, especially ambiguous messages like, "Hope you're well." A day after the story's publication, a WhatsApp message came in from a long-ago lover, a man I used to live with — the one my parents never forgave me for leaving behind. "Hope you're well," it said.

The premise of that column was that out-of-the-blue messages like that can spark confusion and disrupt someone's hard-earned healing process. It applied primarily to exes who ended on bad terms, who haven't spoken for a long stretch of time, or who have things left unsaid.

My response to the WhatsApp message was "LOL," and then the long-ago ex and I moved on to catching up about our lives and families. Why did his "hope you're well" text hit different? Because I have a weird compulsion — almost like a biological need — to stay on good terms with my exes.

I told my long-ago ex that I was working on a column about staying friends with former lovers and begged him to write something mean about me. He said he couldn't, which is a complete lie because I was an absolute psychopath at the end of our relationship.

A few days later, I attended a co-ed baby shower with my boyfriend and ran into my most recent ex. The three of us caught up over champagne, and I loved every second. I thought about how nice it was that we were all together — a year ago, that wouldn't have been possible.

Those are examples of ex-boyfriends who were disposable by nature (no kids together or shared assets). It's a completely different situation with my ex-husband, who is the father of my children. We waste precious working hours sending each other Instagram memes and still choose to take family vacations together because we actually enjoy it.

If this all sounds strange to you (or even ill-advised), you're not alone. I asked my Instagram followers their thoughts on staying friends with exes, and it proved to be an incredibly divisive topic. Their answers ranged from several flat-out "Nopes!" to "Maybes" with qualifiers like, "It depends on the breakup," "Only if you never loved them," or "If you have kids together." My favorite response was, "Only if the spark is gone."

The naysayers believed staying in touch could be manipulative, a sign someone wanted to keep the door open, or just plain unhealthy. Those in favor thought there was no great reason to let go of someone with whom you'd shared a deep bond and happy memories as long as both parties were in a good place about the breakup.

I consulted Dr. Jess O'Reilly, a sex and relationship expert and host of the Sex With Dr. Jess podcast. Her opinion? "Of course, exes can be friends after a breakup." But there are caveats.

A post-breakup relationship needs to have clear boundaries. "Feelings of love and connection need not be hierarchical, and relationships don't always have to follow rigid categories," she says. "So if the romantic and sexual elements fade (or are no longer desired), you can still enjoy the emotional closeness of a friendship.

Emotional bonds also don't dissolve with a breakup or shift in the relationship, so if a friendship feels meaningful, of course you can continue to cultivate it. Folks will argue staying friends means you're trying to get back together, but that's not true for every person or every relationship."

Dr. O'Reilly says the naysayers have a point, too. Not everyone can maintain friendships with their exes, and the dynamic needs to be mutually agreed upon. "We have a tendency to generalize our own personal experiences and assume others must inevitably respond the same way we do, but no experience is universal," she says. "Just because you can't be friends with an ex doesn't mean no one can."

If you're thinking about sparking up a friendship with an ex, Dr. O'Reilly shares some Do's and Don'ts.

Do:
Be clear and honest about what you want.
Make sure the communication feels comfortable.
Respect each other's boundaries.
Be open to the reality that friendships also require investment and undergo ups and downs.

Don't:
Try to get back together unless you know your former partner also wants that.
Be dishonest about your intent.
Stay connected to your ex if it doesn't feel good or is causing you distress. For example, if you're trying to be friends but you're constantly checking their online accounts to see what they're up to or investigating for new relationships, you may need a bit more distance.