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How to Start a Conversation with Your Ex & Not Make It Weird

Talking to an ex is never comfortable, but sometimes inevitable. Know how to start a conversation with your ex so that you don’t make it weird.

How to Start a Conversation with Your Ex

Learning how to start a conversation with your ex might seem overwhelming, but it does not have to be a case of trial and error. Starting a conversation with your ex is just like starting a conversation with anyone else. You can let your history psych you out too much.

Whether you ended on good terms or not, you almost always have to talk to your ex about something. Maybe you left something at their place. Maybe you need closure. Or maybe you want to get back together. Whatever it is, you can do it. You just have to know where to start.

Before starting a conversation with your ex

Starting a conversation with your ex is easier than you might think. As long as you know your reason for reaching out, you can start a conversation with your ex quite easily.

Going in blind is never a good idea when it comes to starting a conversation with your ex. That is how things get messy and out of hand. [Read: A guide to help you decide about being friends with an ex]

Take it from me, I have done this and it never works out. Even asking my ex where he got food he posted a picture of on social media ended up leading to a blame game and discussion about whose fault our downfall was. It was not fun.

Even if you think you are above the pettiness of something like that, trust me, you aren’t. Instead of just reaching out like it is no big deal, think about what you want out of this conversation and start with that.

This person knows you so there is no need for small talk and pleasantries. You, of course, want to be respectful and considerate, but you do not have to text back and forth about your job when all you want is your favorite scrunchie back. [Read: 14 things to keep in mind when you accidentally bump into your ex]

Why start a conversation with your ex

Now that you have thought about why you’re reaching out, think about it harder. Is it really a good idea?

Sometimes reaching out to an ex is just not worth it. If you had a volatile relationship and you want to start a conversation to see how they are doing since the breakup, that may not be necessary.

If you left a shirt at their house, do you really need it back? Will reaching out for something so minor cause more trouble than it’s worth? Is your shirt or hairbrush just an excuse to start a conversation with your ex because you miss them?

Before reaching out, think about your reason and figure out if it is really necessary. I say this a lot but, your ex is an ex for a reason.

With that being said, sometimes we don’t have a choice. Sometimes we need to start a conversation with an ex about family, finances, or something else important. In that case, learning how to start a conversation with your ex will be useful and necessary. [Read: How to deal with the end of a relationship like a grown up]

How to start a conversation with your ex

Figuring out how to start a conversation with your ex will depend on why you are reaching out. If you are wanting to get back together, you will want to start the conversation differently than you would if you want to settle finances or exchange keys.

I’ll try to provide you with a rough idea of how to start a conversation with your ex. Take my suggestions and customize them to your situation and your relationship, and it should work out.

#1 Be straight forward. In most cases, I recommend just coming out with it. Asking how they’ve been and going through the motions will not do anything but prolong the inevitable. If you need to meet with your ex to exchange keys or get your favorite sweatshirt back, just say so.

Send them a text saying you hope they are doing well and then get into it. It can sound harsh but keep it polite and to the point. Think of it as a business email in that way. If you need a coworker or contact to send something over you say something like, “Hi, I hope you are doing well. I’m just reaching out to see if you got my last message.”

This is a blunt approach, but in my experience, it is the most effective. And people appreciate the honesty. [Read: How to breakup with someone you love the right way]

#2 Avoid going too deep. When starting a conversation with your ex, you may feel inclined to reminisce. Unless you broke up recently and need closure, avoid anything that will drag you back into the breakup. They are not your almost ex, they are your ex, so keep them that way.

Even if you are reaching out to be friends, keep things moving forward, not back. If you work together or have mutual friends you can stay cordial, but there is no need to talk about the good old days. Think back to Friends. Every time Rachel and Ross talked about their relationship they hooked up or nearly hooked up and things got complicated.

#3 Ask to meet up. Face to face communication is almost always better than talking via phone. This way there is a less chance of miscommunication. But with that, try to meet somewhere public. This will help keep both of you calm and grounded. It will also prevent any relapsing into old patterns.

If you need closure or want to get back together, I definitely recommend talking in person. Before even getting into too much texting, ask if you can meet up to talk about some things. But, if your relationship was violent or abusive in any way at all and you have to meet up to move out, bring a trusted friend or family member with you. [Read: Are you seeing signs you should get back with your ex?]

#4 Be neutral. Whether your ex cheated on you, stole your money, or ran over your cat, try to remain calm when starting a conversation with your ex. It is likely that your emotions are still running high. You are probably still pissed or upset.

Either wait until you feel calm enough to reach out without the risk of an emotional explosion or have a friend that can stay neutral with you when you reach out. Let them know your goal for this conversation and let them do the talking.

#5 Don’t patronize them. I have seen this happen a lot. I have even been guilty of it myself. When you feel the relationship ended due to your ex’s lack of trust, infidelity, or anything else on them, you may feel better than them. And, keep this between us, but you very well may be.

Whether that is the case or not, try to speak to them as your equal. Even if you don’t feel that way, being kind without going over the top is the best way to handle any ex situation. They know you and they will know if you are treating them differently.

#6 Remember your strength. Often time we reach out to an ex for reasons that are just hiding the real reason. We miss them. Even if we don’t want to get back together, we want just a taste of that feeling we used to have. We want to remember that safety and comfort.

That is totally normal, but try not to give into it. When you start a conversation with your ex, keep your eye on the ball. Go in with a focus and a desired outcome and stay focused on it. Remember that you are strong on your own and this relationship and this breakup do not define you. [Read: 8 most common post breakup mistakes you shouldn’t commit]

#7 Be respectful. This is a general rule for every interaction you have with everyone in your life. But, I find it needs to be repeated, especially when you are figuring out how to start a conversation with your ex.

Respect is the only thing that is keeping things fair and calm. As soon as one of your loses respect for the other, things are imbalanced and can go awry quickly.

[Read: How to get through the 10 stages of a break up]

Next time you are wondering how to start a conversation with your ex, come back here to make sure you handle it with poise and grace.

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Samantha Ann
My name is Samantha Ann. I am 28 years old. It was always my dream to become an advice columnist, so after years of off and online dating and eventually finding...

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