I Go Out to Dinner with My Ex Every Few Months—Here’s Why It Works

Plus, relationship experts offer their tips for staying friends with former flings.

You hear it in the movies, and probably in real life from a brief Bumble fling: “This isn’t working, but I really want to be friends.” Cue the eye-roll emoji. Staying friendly with an ex is a slippery slope, and nine times out of ten, the post-breakup friendship is short-lived. But for me and my ex-boyfriend of two years, it’s been smooth sailing. Hold the eye-roll emoji, and hear me out on this one. I credit our friendly terms to both of our maturity—not to toot my own horn—but even more importantly, the foundation of friendship our relationship was built on has made the post-breakup waters easy to navigate.

Joe and I fell in love in 2014 as awkward 17-year-olds who had no idea how to be in a real relationship. As newbies to the boyfriend-girlfriend dynamic, we learned everything together along the way. We quickly became best friends, as young first loves often do: through failing miserably as AcroYoga partners in P.E., competitively playing Trivia Crack across the room in calculus class, and creating enough inside jokes to fill a journal—literally. And after four years of dating we had grown from naive teenagers to 21-year-olds trying to figure out another totally foreign thing: how to become real adults. This time, the question was: Were we going to tackle this learning experience together or apart?

As we began our senior year of college, the fact that Joe was the only guy I’d ever had a serious relationship with—and vice versa—began to weigh on me. Neither of us had been truly single since we were 17, aka completely different people than we were at age 21. In nine months, we’d be tossing graduation caps in the air and stepping into the world as “adults” in two different parts of the country: Iowa and New York. With this imminent divide approaching, the time had come to really figure out if we were each other’s “forever.”

That might sound dramatic, but how are you supposed to know if you’re meant to be with someone if you’ve never been with anyone else? I decided that the only way to know for sure was to break up with him. You don’t know what you have until it’s gone, right?

Our breakup was a shock to Joe, and undoubtedly the hardest thing I’ve ever done, to this day. Ending a relationship is never easy, but it’s especially difficult when there’s nothing actually wrong with the relationship. After a tearful few hours explaining how I felt and Joe being the understanding, kind guy he is, we agreed that breaking up was the right choice. I walked back to my apartment where my friends were waiting for me with hugs and pints (yes, plural) of ice cream, which I ate while crying and questioning my decision, naturally. During the following weeks, I continued to wonder if I made the right call, which led to me sending Joe some too-soon jokey texts that were not super well-received. Cringing emoji.

But as senior year crawled on, I slowly realized that I had needed this period of time to grow as an individual—and what I found was that I’d outgrown our relationship, as beautiful as it was.

When someone is your best friend—the person you trust, have the most fun with, and lean on more than anyone—for four years, it seems frankly tragic to me that you could cut them out of your lives forever.

Even if there isn’t a romantic connection there anymore, can’t you still be a part of each others’ lives in some capacity? Luckily for me, Joe has that aforementioned thing called maturity, so, he agreed that we should be friends—which felt like a weight off my shoulders.

A few months post-breakup, we started meeting for coffee or lunch. Our transition from boyfriend-girlfriend to simply friends was weird at first. When we’d be sipping from mugs at a cafe, thoughts would run through my head like, “Should I not have put my hand on his knee as I laughed at his joke?” and “Am I staring at his ridiculously long eyelashes for too long?” I didn’t want to cross any lines—having been the bitch who broke his heart—but it was hard to break these habits that had become as natural as breathing for four years.

The more we saw each other, the more comfortable we became, and, eventually, we fell into our old rhythm of banter. We started sending each other playlists again, and when we’d see each other out at bars, it didn’t feel awkward to hug and chat for a few minutes. By the end of senior year, we were hanging out in small groups of friends, picking each other as beer pong partners, and feeling completely at ease. I knew I’d made the right decisions: both breaking up with him and choosing to hold on to him as a great friend.

should you stay friends with an ex?

When I moved to New York City after college in 2019—achieving a goal ten years in the making—Joe was the first to congratulate me, and he wanted to hop on the phone to hear all the gritty details a few weeks in.

When you share your hopes and dreams with someone for years—especially during pivotal years like high school and college—why wouldn’t you want to share in their excitement and pride when they achieve those goals, regardless of your relationship status? I’m lucky Joe agrees with me on that notion.

When I visit home every few months, Joe is high on my list of people I make sure to see. We’ll meet for dinner and spend hours catching up on each other’s lives over pizza, which makes me miss him, yes, but it also reminds me that there’s no romantic connection there anymore, and we’re both where we’re supposed to be. Joe and I have watched each other grow from insecure teenagers into full-fledged adults, laughing along the way and sharing a mutual pride for everything we both accomplish, which has helped us maintain a strong friendship for six years.

Staying friends with an ex might sound daunting—and it will feel unnatural at first—but if you are truly important to each other, the initial struggle is worth it. But don’t just take the advice of a 23-year-old with one serious relationship under her belt; listen to these relationship experts’ tips for how to maintain a healthy friendship with an ex.

1. Give each other time to heal.

When a relationship ends, it’s natural to want to reach out right away—but even though you’re likely missing the shit out of them and wondering how they’re doing, everyone needs time to process. Even if you had a 100% amicable breakup or if you were the one who ended things, you need to give the person space. And definitely don’t text them a stupid joke that brings you back into their mind while they’re still healing. (Guilty.)

“If one or both partners are grieving the relationship and struggling to move forward, taking a time-out can provide necessary emotional distance and healing time,” Dr. Carla Manly tells HelloGiggles. “For some people, a break of several months is sufficient to allow for a friendly reconnection, whereas others need more time.” 

2. Be honest about your hopes for the friendship.

If you’ve landed on the “let’s be friends” decision, be upfront about where your true intentions lie. “If one of you is still hoping to reconnect romantically and the other is not, you may want to adjust the boundaries to ensure that they’re clear,” Jess O’Reilly, PhD., host of the @SexWithDrJess Podcast says. “If your ex is only sticking around in the hopes of a romantic future, consider whether or not being friends works for you both.”

Okay, Joe and I did drunkenly kiss once or twice after breaking up, which blurred the friendship line. But after each late-night boozy kiss, we had honest conversations about how we didn’t want to jeopardize our friendship by letting things go further, and we were frank about how we had each moved on—which made the situation laughable when we ran into each other three times on campus the next day.

3. Decide what type of communication works best for both of you.

For some exes, in-person meet-ups are too stressful or painful. Phone calls are an easy way to stay up-to-date on an ex’s life without re-opening the wound that physically being near someone can cause. If hearing your ex’s voice still hits too close to home, chatting over text is the least risky way to keep in touch—but beware that the tone of texts can often be misunderstood. When it comes to meeting in person, consider if dinner is too intimate of a setting, and opt for getting coffee or going for a walk instead.

“The activity or means of communication matters less than finding a degree and type of contact that is mutually acceptable and beneficial for both people,” Dr. Manly says.

When it comes to talking about each other’s love lives, Joe and I are vague. We wish each other luck with new romantic prospects, but come on: We’re not girlfriends dishing the dirty deets over a bottle of wine. But we are still each other’s biggest cheerleaders. Case in point: He’ll probably read this article without me sending it to him. Which, on second thought, maybe I should have warned him that I was airing our dirty laundry before writing this? But I don’t think he’ll mind—we’re that good of friends.

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