1. It is too soon. Being friends with an ex right after the two of you broke up is, as much as I hate to admit it, impossible. You must allow yourself time to go through your emotions and distinguish your love feelings for the person from those that are still acceptable in a friendship. Winter recommends at least six months before making any regular contact with your ex, so that you can see them as people rather than lovers.
2. You are doing it for the wrong reasons. Be honest: Do you want to remain friends with your ex because you want to spend time with them? Because you are not prepared to move on? Because you want to ensure they aren’t ready to move on? Being friends with an ex is only effective if you’ve both truly moved on from the relationship, and using friendship to postpone that process is unhealthy.

3. You are using friendship as a ploy to get back together. If you’re truly ready to be friends with an ex, it signifies that your desire to date them has completely faded. “If spending time with your ex makes you want to ‘get them back,’ don’t. “If being a friend is a ruse to spend time with them, don’t do it,” advises Winter. Don’t try to persuade your ex to be romantically involved with you under the pretext of friendship; you’ll just injure yourself.
4. If one person is more invested than the other, the friendship won’t work, regardless of sexual history. If you’re continually texting, calling, or attempting to make plans with them and receiving no response, the two of you may have different expectations of the type of friendship you seek. 5. The boundaries are blurred.
When you finish a relationship and transition to friendship, all sexual behavior is off the table.
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“It doesn’t involve explicit discussions about sex, or include sexual flirting,” Winter shares. If these boundaries are being pushed or violated, or if it’s simply too difficult to keep your hands away from each other, it may be time to reconsider. 6. You are overly reliant on one another. Deciding to be friends with an ex is more of an agreement to “play nice” than a request to be #BFFs.
“Being a friend with your ex doesn’t involve chatting on the phone all-night or gong out for drinks right after your breakup.” Your relationship ended for a cause, and your ex shouldn’t be your “person” any longer. You should no longer be revealing your deep dark secrets with one another; emotional space is required for it to operate.
7. You are preventing each other from forming new relationships. Depending on where you are in the “getting over each other process,” being friends with an ex may prevent you from being open to meeting new people, especially if you are still hoping that the two of you will reconcile. If your ex is still taking up space in your life that should be reserved for a boyfriend or girlfriend, such as the person you text all day or talk to on the phone at night, you might consider giving each other some space.

8. Your significant other has an issue with it. Friendships with ex-partners work best when both of you have gone on to new relationships, but if your friendship with your ex was really close (which is not recommended), it complicates things for everyone when a new third party enters involved. If your significant other believes you and your ex are too close, or if the friendship is interfering with your relationship, it may not be worthwhile to stay together.
9. There is any level of jealousy. “If there’s jealousy, it means friendship is a guise for getting back together,” Winter explains. If you still have romantic feelings for an ex, seeing them with someone else can be sad and terrible (believe me, I know). If your ex has started a new relationship and you are feeling envious, it may be time to quit the friendship or at least put it on hold until you can look at their new relationship objectively.