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When you should (and shouldn’t) stay friends with an ex

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On my way out the door, he asked if he could still text me occasionally. A soft way of asking if we could remain friends.

“I don’t know,” I said. “I’m going to need some time.”

We’d just finished the second round of a breakup talk at the end of a relationship that was three months but felt like six. Three months spent in that space between like and love, trying to figure out if we were going to really do this or cut and run. He chose the latter. And while I was upset, I was also relieved that a decision had been made. There’s only so long a relationship can remain in limbo.

After we said goodbye on that spring day a year ago, I thought about him a lot and wondered how he was doing. But I was determined to get over this one without talking to him. We didn’t see or talk to text each other.

Until I ran into him at a day-long meditation seminar in October. There were about 200 people there, so I don’t think he noticed me until I walked up to him at the end of the day, and said I was ready to be friends. He suggested dinner sometime; I countered with coffee.

But once I got home and thought about following up to schedule that coffee, I didn’t. Guess I wasn’t ready after all.

As I thought about how many exes and quasi-exes I already have as friends, I wasn’t sure I wanted or needed another one. Most of them I’ve collected in my 20s. They’ve given me dating advice and vice versa. At this point, we’re more friends who dated a really long time ago than “exes.” Two of them, I’ve danced at their weddings. One of them started a book club that I’ve been part of for years. I’m not pining for any of them; rather, I want them to be happy, just as I’m sure they wish the same for me.

How do you decide whether to keep an ex — or merely someone you dated — in your life after the spark has gone out? Sometimes you don’t get much of a choice. If you have kids together, you might be co-parenting or at least communicating. But if you do get to decide, there is no Google Calendar alert that pops up to tell you the timing is right. There are no 36 Questions to Fall Into Friendship With an Ex.

When I spoke to a few dating coaches and writers on this subject, a few guidelines emerged that I wish I’d known a decade ago. (Though who knows if I would’ve followed them back then!)

The first thing that stood out was that you need time apart after a breakup; do not try to be friends immediately.

This sounds easy, but it’s the kind of thing you only really understand in hindsight. In my early 20s, I neglected to take such a break when my college boyfriend and I quickly slid into a friendship of frequent phone calls and cross-country visits. The support he offered at that time, when I was just starting out in a new career and in a new city, was incredibly valuable; in a lot of ways, the long goodbye was wonderful. But we were probably kidding ourselves about the friend thing; what we were doing was more akin to a long-distance relationship.

“If you always have one foot in the ex door, how can you be open to someone new?” says online dating coach Erika Ettin, founder of A Little Nudge. After some time apart, Ettin says she encourage singles to think about why they might want to stay friends with an ex. “Do they see qualities that add to their life, or is it because they’re lonely and they don’t want to be alone?” 

Much like being in a romantic relationship, remaining friends with an ex requires that you’re both looking for similar things. Dating coach Francesca Hogi told me that she often sees exes trying to be friends when one person still has feelings for the other and is holding on to hope of reconciliation; or someone is still hurt from the breakup, and that makes it hard to continue any kind of relationship.

She also notices women agreeing to be friends when an ex suggests it, just because they don’t want be disagreeable. “You should just really honor your own sense of self-preservation and feel okay saying to someone: ‘Actually we’re not friends. We’re not going to stay in touch,'” Hogi said.

Hogi has a litmus test for deciding whether to be friends with an ex: “If I met someone who I thought would be a great match for my ex, would I introduce them? For most people after a breakup, the answer is no.”

All the exes and quasi-exes I have as friends would pass that test now, but they certainly would’ve flunked when we began as friends. Now that I’ve reached my 30s, and my social circle is pretty solid, I’m less likely to claim that breakup consolation prize.

Mandy Len Catron, author of the forthcoming book “How to Fall in Love With Anyone,” says the desire to be friends with an ex might be linked to the desire for a clean and tidy narrative. “In general, I think the way that we talk about former relationships is fairly limiting or limited,” she said. “So often we frame relationships that ended as a failure. Maybe if you stayed friends, you’d be less likely to think that a relationship that ended was a failure.

“We would benefit more of thinking of previous relationships as meaningful experiences that existed for however much time they did. They were important parts of our lives — even if they weren’t what we wanted or hoped they would be.”

In this way, remaining friends — or friendly — with an ex can serve as a kind of time capsule. Ettin, the online dating coach, has an ex-boyfriend she dated when she was 22 and had just moved to Washington. Thirteen years later, they still meet for lunch annually. “He defined D.C. to me when I moved here at 22 years old. So it’s comforting to see him,” Ettin said, adding that they like to reminisce about what it was like to live in the city 13 years ago. 

Last week, my ex from a year ago texted to ask if I wanted to catch up over lunch. I’d never followed up from the fall, and six months later I was ready for that catch-up. What were once strong feelings for him had faded to a simple fondness; the pain from the breakup a year ago was gone. As we said goodbye and traded “nice to see you’s,” I thought about how it was merely nice to see him. The lunch was remarkable for being unremarkable.

We made no halfhearted promises to see each other again soon. And that was just fine.

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