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

It’s rarely comfortable when you talk to an ex, but it doesn’t have to be like that. Learn how to start a conversation with your ex and forget the cringe!

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. But at the end of the day, they’re just a person.

Sure, you might have seen each other’s private bits, but so what?

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. It’s always a good idea to know how to do this in a mature way, even understanding how to start a conversation with your ex over text can help you overcome the cringe-factor.

[Read: Should I talk to my ex? 15 revealing questions to find your answer]

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. That’s the crux of it – you need to have a purpose to lead with. Without that, it just looks like you’re trying to speak for the sake of it, or worse, you’re trying to hook up!

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]

Even asking your ex where they got the food they posted on Instagram could end up with a messy blame game and reminiscing about things you don’t want to talk about. It’s not fun. Avoid at all costs!

Even if you think you are above the pettiness of something like that, trust us, 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 cool things to keep in mind when you accidentally bump into your ex]

Do you really need to talk to 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? [Read: How to get over your ex in a healthy way for your future]

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

With that being said, sometimes we don’t have a choice. Maybe you 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 over text or in person will be useful and necessary. [Read: How to deal with the end of a relationship like a grown up]

Does it really matter what you say?

Oh hell, yes!

Obviously, it depends on how the relationship ended as to the tone of your message or conversation but you need to start the conversation in an adult and mature way. That means being polite and kind. You might not want to be, but remember to be the bigger person here.

You don’t want to be flippant or sarcastic. There may still be some hurt or even bad blood between you and the reason for wanting to start a conversation shouldn’t be to just poke a sleeping bear, so to speak!

Ask yourself why you want to contact them and then move from there. [Read: The simplest tips to avoid being rude in any situation]

How to start a conversation with your ex, minus the cringe

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.

Take these suggestions and customize them to your situation and your relationship. That way, it should work out. [Read: How to text your ex after no contact and not make the same mistakes]

1. Be straightforward

In most cases, we 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. Just texting them “hi” will only confuse them, and make them wonder about your intentions.

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 our experience, it is the most effective. And people appreciate honesty. [Read: How to break up 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. Just literally say what you need to say and that’s it. [Read: 20 best questions to ask your ex after a breakup to find closure]

3. Ask to meet up

Face-to-face communication is almost always better than talking via phone. This way there is 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, we 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, take 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. [Read: 15 signs your ex is pretending to be over you and what to do next]

5. Don’t patronize them

We have seen this happen a lot. 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 an ex situation. They know you, and they will know if you are treating them differently. That will affect how they respond to you. [Read: How to talk to people in a charming way no matter who they are]

6. Remember your strength

Often, we reach out to an ex for reasons that are just hiding the real motive. 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 the desired outcome and stay focused on it. Remember that you are strong on your own and this relationship and subsequent 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, we 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 you 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]

How to start a conversation with your ex over text

Without a doubt, the easiest way to start a conversation with your ex is to do it via text or messaging app. That way, you don’t have to see them and you’re not as likely to fall into old patterns.

Of course, messaging has its downsides too – you can easily be misunderstood if you don’t word your text carefully.

The single best route when it comes to starting a conversation with your ex over text, whatever the reason for the conversation, is to be bright and breezy. Don’t apologize for getting in touch or say “I’m sorry to bother you”, there’s no reason to be sorry.

Just say “Hey” followed by whatever it is you need to say. So, if you want to get your sweater back, say “Hey, can you drop my sweater off at …. the next time you’re there please?” Just be polite and say what you want. [Read: Texting anxiety – How to send and receive texts without freaking out]

Will it lead to a back and forth exchange? Well, that depends whether you want it to or not.

A small message can often be a catalyst for further chat but ask yourself whether that’s your aim. If it is, then fair enough, but if not, just keep it quick and concise. Say what you want to say and get out of there!

The beauty of learning how to start a conversation with your ex over text is that you can think about what you want to say beforehand. Make sure you word it clearly and don’t leave anything open for interpretation. That way, you won’t be wishing you had or hadn’t said something. Also, remember to avoid putting kisses at the end – the time for that has gone! [Read: How to respend to a text from your ex and make them leave you alone]

Know when to end the conversation

Don’t drag the conversation on just because you want to keep talking to them. If they start giving you one-word answers or it seems like hard work, let it go.

Remember, they’re your ex, they’re not your friend. If they want to talk to you, you’ll know. They’ll play an equal part in the conversation and it will flow. However, if it’s stagnant or it just seems like you need to keep reviving it, simply come to the conclusion that they’re not interested in talking.

Regardless of why you reached out to them in the first place, trying to keep a dead conversation alive is nothing short of awkward.

[Read: 15 reasons why your ex still texts you and stays in touch with you]

Next time you are wondering how to start a conversation with your ex, follow these tips to make sure you handle it with poise and grace.

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The editorial team of LovePanky comprises relationship experts and real-life experts that share their experiences and life lessons. If you want the best love ad...