Episode 11 was our first listener question. Someone wrote in and asked, more or less: should I get back together with my ex? We opened with a disclaimer we meant: neither of us has pulled off a reconciliation we’d call a success. So what we could offer was what we’ve learned the hard way.
We both drew on our own experience, and we kept the details where they belong. What came out of it was a set of questions we wish we’d asked ourselves first.
Neither story is a how-to. But between them, the same handful of questions kept coming up. So here they are, pulled out and lined up, for anyone with their thumb hovering over that name in their phone.
Five questions to answer before you send anything
Answer these on paper, not in your head. Your head is where the 2am version of you lives, and he is a terrible judge.
- Can I be completely honest, including about my own part? Not “honest” as in finally telling them everything they did wrong. Honest as in saying the stuff that makes you look bad. If you can’t name your own faults out loud, you’re not ready for the conversation that has to happen.
- Will they own what they did, and will I own mine? Before going back, both people need to be able to say, in effect, “this is where I failed you.” If either of you is still at “I didn’t do anything wrong,” that’s your answer for now.
- Can I forgive all of it, not just most of it? If you stay, you have to forgive everything and move forward without it. Not most of it. All of it. If you go back carrying the thing that broke you up, you’re not starting a new relationship. You’re resuming the old one, and you already know how it ends.
- Why am I really going back? Be specific. Lonely? Dating has been rough? It’s comfortable? Ego? None of those are the right reason. The right reason sounds more like: this person is someone I want in my life, and I’ve thought about what we’d build, not just what I miss. And check whether you’re going back to the person they are now, or the person you remember.
- Am I okay on my own? Jason’s point: if you’re not happy with yourself, you probably won’t be happy in the relationship either, and you’ll blame the relationship for it. If your honest score on yourself is low, start there first.
If you got clean answers on all five, you’re in a better spot than most people who hit send. If you stalled on one, that one is your homework.
Watch for the ego move
This is the part of Jose’s story that stuck with both of us. He wasn’t actually indifferent. He was hurt, and he dressed it up as not caring because that felt safer. The cost was the one conversation he wanted most.
Jason’s take was that if anything is going to happen, even just a conversation, somebody has to drop the act first and say the vulnerable thing: this hurt me, and I still think about you. If both people are waiting for the other one to blink, nobody talks.
A quick gut check: if you’re planning how to look when you see them, you’re in ego territory. If you’re planning what you need to say, you’re closer to the real thing.
A lot of relationships can be salvaged with good conversation. But you have to be willing to be completely and brutally truthfully honest.
Hope is not a plan
Jason had a colorful way of putting this that we had to bleep. The clean version: hope can build you up and let you down real fast. If you’re pinning everything on one conversation or one grand gesture, the flowers, the surprise visit, and it lands flat, you’re not back at square one. You’re behind it, with the wound open again.
Before you reach out, write down what you’ll do if they say no, or say nothing. If you can’t stand that outcome yet, you’re reaching out for relief, not for reconciliation. Give it more time.
If you do have the conversation
Jose closed the episode with something close to a script, and it’s worth borrowing. Figure out what you want your life to look like first, on your own. Then go to the other person and say, plainly: this is what I want moving forward, are you going to come with me and help build it?
That framing does a few things at once. It keeps the conversation about the future instead of relitigating the past. It makes room for the possibility that you’ve both changed. And it gives them a real question to answer, not a feeling to manage.
As Jose put it, if you can’t agree that your future is something you build together, what is the point? Independent goals are fine. But there has to be a shared one, or you’re just two people living in the same house.
Curiosity builds the door that’s there, but that doesn’t mean that you need to open that door.
This list assumes the breakup was about broken trust, drifting apart or two people not handling things well. If it involved abuse or you didn’t feel safe, these questions aren’t the right tool. Talk to someone qualified before you talk to them.
Your turn
We’re pro “do you.” Not against getting back together, not against moving on. If you’ve been on either side of this, tell us in the YouTube comments on the episode: which of these five questions would have changed your decision if you’d answered it honestly first?