The One Question to Ask Yourself Before Trying to Stay Friends With an Ex

DEAR DR. JENN,

After three years together, my boyfriend broke up with me, and I'm still struggling. I still think of him as one of my best friends and confidants, and I don't want to lose him in my life. I want to be friends but don't know if it's truly possible or healthy for me long-term. Can exes ever really be just friends? —Friend, No Benefits

DEAR FRIEND,

Staying friends with an ex can feel like the ultimate sign of maturity. So much so that the intention to stay friends is usually included in most celebrity breakup announcements these days. (Of course, sometimes it's just easier PR-wise. Remember J.Lo and A-Rod's joint statement that they realized they are "better as friends and look forward to remaining so"?)

But the thing is, not every couple is destined to be Jennifer Aniston and Brad Pitt (or Justin Theroux for that matter!) or Gwyneth Paltrow and Chris Martin. In fact, unless there are shared children in the picture, I generally am not a fan of the idea of staying friends with your ex.

That's not to say it can never work. But if you do want to give it a shot, I recommend first examining your true motives. A study that examined why people maintain friendships with exes found four reasons: security (emotional support, advice, trust), practicality (shared possessions or finances), civility, and unresolved romantic desires.

Needless to say, deciding to stay friends with an ex because you aren't over them romantically — and want to leave the door open in case they change their mind about the breakup — is definitely not advised and will only hold you back from being able to move on.

If you're unsure where you fall, this list should help you decide.

Six reasons not to attempt a friendship

Plus, the single most important question to ask yourself to figure out if you can stay friends with your ex.

1. You can’t separate.

In my clinical experience, taking time off from all contact immediately after a breakup is beneficial. This is the time for boundaries. Having clear-cut rules of engagement is crucial to your healing process. This detox time allows you to let go, grieve the loss of the relationship, and have some distance which gives you a new perspective. I always recommend taking one year of space, no less than six months.

If after taking that break you still want to be friends and you can answer the question I propose at the end of this article in the affirmative, well, you might have a potential friendship to develop!

2. One of you still has feelings for the other.

Typically, one person wanted to break up more than the other. Therefore, one of you is likely to still have romantic feelings. Spending time together when you have romantic desires is messy. Think about it: Are you spending a lot of time dressing up, trying to look fabulous, and seem cool and desirable to your ex before your "platonic" hangouts? If so, you aren't just being friends — and you are setting yourself up for disappointment.

Hanging out with your ex when there are lingering feelings in either direction prevents you from grieving the loss of the relationship and feeling the feelings you need to experience in order to let go. It creates a sense of denial about whether or not the relationship is really over. In order to be available for a healthy relationship — either as friends with your ex or romantically with someone else — you must grieve the loss and let go first.

3. You still hook up, or may if the mood strikes.

After a breakup, there is likely to be leftover sexual chemistry. Not that long ago, the two of you were sleeping together! When a breakup is recent, those sexual feelings are probably still in the air. This really complicates the whole "just friends" endeavor if there's any possibility of adding "benefits." If it's not a clean break, there isn't a possible pathway to friendship.

4. You’re looking for a serious relationship (with someone new).

Let's be real: Your ex is likely to be a cock block. When you are spending time with your ex, it means you have less time and energy to spare for meeting potential new partners. Plus, when your emotional needs are being met by a former flame, you are less likely to open your heart and give any suitors a real shot. In fact, a recent study found that people who still have longing feelings towards their exes tend to have less successful relationships with new people. Who needs that?

You might be asking yourself, "Who needs a new boyfriend that is jealous or uncomfortable with my dear friend who happens to be my ex-boyfriend whom I used to sleep with?" And that is a very bad sign! It's fair and expected for potential new partners to be uncomfortable with you confiding in your ex about them, or still going out drinking with him, and nurturing the bond you share. That energy is better used towards building a new healthy relationship that has the potential for a future.

5. You’re extremely invested in if or whether your ex is dating again.

All too often, I see people stay friends with their former partners in order to keep an eye on their dating life and attempt to influence it. Advising him against the hot girl he met in the bar is not being a protective friend, it is an attempt to manipulate his future love life, or even keep him to yourself. This is not good for either of you.

In my clinical experience, people tend to be more likely to want to stay close to their ex when they have a sense of dating scarcity or believe that they cannot do better. But spending time with an ex only reinforces these dating anxieties and is harmful. If this sounds like you, don't waste time being friends.

6. Friendship feels like a consolation prize.

If you started out as romantic partners, downgrading to a friendship is likely to be less than stellar. A study of the friendship between exes found that the more romantic desire was present, the lower the quality of the friendship will be — no surprise there. This means you have to be really honest with yourself about whether or not you still have feelings in order to assess whether or not an honest friendship is even possible.

So, can you and your ex stay friends? Ask yourself this one question:

The single most important question to ask yourself is, "If my ex met someone new and fell madly in love, would I be genuinely happy for them both?" Can you see yourself going out to dinner to celebrate with your ex and their new partner — even if you are still single? This is the ultimate litmus test you must hold yourself to. If you cannot honestly answer that you would be comfortable hanging out with them both, and truly happy your ex had met someone, you should not be hanging out.

Ideally, you would wait six to 12 months after a breakup before even asking yourself that question. And if there ever was any abuse in the relationship, don't ask it at all — focus on getting distance and moving on.

After any breakup, you want to ensure that you put your well-being first. If you're doing that, and you can answer a resounding "yes" to this question, then, sure, your ex can be a friend in that time of growth and need.

In Hump Day, award-winning psychotherapist and TV host Dr. Jenn Mann answers your sex and relationship questions — unjudged and unfiltered.