John Cusack holding up a boombox in front of a car from Say Anything

Just the Tip is a sex and relationship column hosted by queer non-monogamous kinkster Jera Brown. Here you will find interviews with sexuality researchers and educators as well as smart and compassionate responses to anonymous questions. If you would like to be interviewed or have a sex or love question you’d like Jera to answer, email or DM Jera on Instagram or Twitter @thejerabrown.

My ex-boyfriend recently reached out after a couple of years of complete silence. He apologized for not being mature enough to be with me and said he regrets it. He asked if I’d be interested in reconnecting. How do I know if this is a good idea? I fell for him hard and he didn’t treat me very well. I always felt like he had the potential of being a great partner if he was willing to work on himself and it seems like he’s finally been doing that, but is there any way to know whether it’s going to be different this time?

There are plenty of cases of people returning to each other and having healthier relationships the second go-around. Often this happens when two people really learned from the relationship and did the work to be healthier partners.

After all, there was a reason you were attracted to each other in the first place. 

But it’s just as likely you’ll fall back into old patterns.

You asked if there’s any way to know whether things might turn out differently this time. Here are six questions to ask yourself.

Related post: My Relationship With My Partner Improved After We Broke Up

1. What do your friends say?

This is one case where it might be worth your while to crowdsource advice. Sure, no one knows better than you what the relationship was truly like. But your friends will know how the relationship affected you in a way you’re unable to see for yourself.

They’ll know what this person brought out in you and what you were like when you were together.

Considering the fact that you said he didn’t treat you very well, I’m guessing your friends will be protective of you, as they should. If their response is “Oh hell no!” I’d think hard about re-engaging with your ex. 

You might be feeling very nostalgic and seeing the relationship with rose-tinted glasses, but your friends will remember all of the pain and heartbreak.

2. Is there evidence that he’s truly grown?

If he’s admitted that he wasn’t mature enough to be with you the first time, then part of what you have to weigh is whether he’s more mature now. 

Do you have any mutual friends to ask if they’ve seen a change in him? Do you have access to his social media accounts? Is anything different? 

I’m not encouraging you to go on a stakeout or break into his email or anything. But if there are some publicly accessible ways to see that there’s proof of his supposed self-work, it would be worth looking for.

3. Are you emotionally prepared for it?

Let’s consider the worst possible scenario for a moment: that you get back together and it’s as bad as it was before.

Sometimes there’s a false sense of safety in getting back with people we know well. It’s a “the devil you know” scenario. You might be thinking you know how bad it could possibly get because you’ve “been there, done that.” 

But it’s hard to really hold on to the poignancy of painful experiences. This is human nature, of course. Our brains protect us from searing pain by letting it fade with time. 

Before you say yes, try to remind yourself of what it was like. If you journal, go back and revisit your entries from this time. Look at your texts or emails with your ex or with your friends at the time. If this is all too difficult or painful, take that as a sign.

4. Is he owning up to his behavior and its consequences?

So he apologized for not being mature enough at the time. This isn’t the same thing as apologizing for his actions or how he made you feel.

If I were you, I’d want a better apology. Before restarting a romance or a physical thing — maybe even before meeting up in person, consider asking him some follow-up questions about your relationship.

What kind of reflection has he done on it? What did he learn? What steps has he taken to change bad patterns? Does he have a therapist?

5. Have you done your work?

So far, all of my advice has been looking for signs that your ex has changed. But have you? Unhealthy situations take two.

For starters: if he treated you poorly the first time, why did you put up with it? Have you really reflected on this? Do you have higher standards for yourself now?

If you’ve dated since, I’d spend some time looking at patterns in your behavior, who you’re attracted to, what the communication was like, etc.

This is a good thing to do regardless, especially at the start of any relationship. The more you know about your patterns, triggers, strengths and weaknesses, the more you can walk into a situation prepared.

Related post: Why Was the Sex Better in Past Toxic Relationships?

6. Why are you considering it?

Last one: I’d do some deep reflecting on why you’re considering returning to someone that didn’t treat you well in the past. 

You need to be really honest with yourself.

Are you lonely? Do you know what you deserve (which is better than what you got the first time)? Is there something about this person you’re looking for or believe you need — but does it need to be met by your ex?

As you do this soul-searching, I’d create space between you and your ex. If he’s really interested, he’ll wait.

Disclaimer: As always, there’s no perfect solution to any relationship issue and you may benefit from the help of a neutral, trained professional. Jera is not a licensed mental health professional, just a writer living as authentically as they can.

Jera writes about sexuality, spirituality, and social justice. They are the author of Just the Tip, a queer-friendly, sex-positive, relationship advice column and the editor of Sacred and Subversive,...