How To Connect Emotionally With Your Ex

In this article, you’ll learn how to turn your awkward or boring small talk and the like into exciting, fluid, and meaningful conversations. And by extension, dry and dull dates into ones that are fun, memorable, and that ultimately bring you and your ex closer together.

To be clear, some people are naturally more charismatic and socially calibrated than others, with a, therefore, higher capacity for building emotional connections. This is a simple truth. However, what is woefully untrue is that you can’t become someone more charismatic and socially calibrated.

The truth is, if you’re currently awkward, inhibited, and socially uninspiring, you can change that. Despite being genetically predisposed, your capacity for connecting is not set in stone. It’s merely a skill you can consciously improve through practice — just like any other skill like cooking, mastering a musical instrument, or getting good at chess.

So in the name of improving your skill for connecting, I formulated a series of activities designed to help you with the feat, largely based on improv comedy, acting classes, social psychology, and various public speaking courses I took over the years.

Make no mistake, however. Most people expect these activities to be logical, and while a minority of them are, most aren’t. Why? Because connecting with another person is an emotional process, not a logical one. It’s not about 1-2-3 formulas, steps, or techniques, but rather creativity.

On a final note, while I did provide a large, perhaps overwhelming, number of these connecting activities, try them all out regardless. Because it’s only through deliberate implementation and a commitment to the craft that you truly can bridge those emotional gaps and reignite a deeper connection with your ex.

Anyhow, onwards to the activities.

Activity #1: Work On Spawning Greater Self-Awareness

Without much self-awareness, you’ll rarely notice things like when you’re being too saccharine, pushy, self-indulgent, or how you’re droning on an irrelevant tangent that doesn’t interest your ex or even turns them off. And since you don’t notice these sabotaging behaviors and fail to change the subject or your approach soon enough, you usually just talk your ex out of liking you.

Now there are many ways you can develop adequate self-awareness and avoid these unnecessary blunders and the drama that comes with them. Introspection, journaling, dating other people — all of this is obvious.

But what is not always so obvious is just how much a video journal accelerates things when added to the mix. While awkward and difficult, this is arguably the best way to spawn self-awareness and, ultimately, get you to see yourself exactly as your ex sees you — physical warts, behavioral tics, confidence gaps, and all.

So here’s how to make your very own video journal.

First, set aside about 5 to 15 minutes and record a video of yourself talking. Keep this up for the next 30 to 60 days. Use your phone’s camera or your computer webcam for recording. And don’t worry about editing the footage. While you’re welcome to do it, it isn’t required. Just be sure to save it somewhere so you can review it later.

For the first minute or two of recording, talk about whatever you want — no matter how trivial or unimportant. The point is just to get some initial momentum. Then transition to talking about what’s going on in your life.

A few ideas: how’s your dating life going, how’s your career unfolding, what’s important to you at the moment, or how you feel about your ex and the breakup. Be sure not to only talk about facts and random thoughts. Rather, mix the two with interesting stories and reasoning.

Once you’ve recorded your video, play it back to yourself and observe how you come across.

• Are you presenting your thoughts well?
• Are you drifting to random tangents mid-thought?
• Is your delivery impactful?
• Could your rhetoric be more engaging and lively?
• Could your posture be more confident?
• Could your voice tone be more natural?
• Are you emphasizing your ideas with conviction?
• Are you transitioning from point to point elegantly?
• Are your thought flow crawling with fillers like “ums“ or “ahs?”

After pinpointing how you could sabotage your dates and interactions, pick one flaw and work on it on camera. So if your problem is, let’s say, that you’re talking with a meek voice tone, that’s probably because you’re breathing with your chest. Therefore, try recording a video of yourself speaking while only breathing from your diaphragm. It also helps to have vivid hand gestures and a proper, straight posture.

Once you’ve got better in a particular troubling aspect, move on to overcoming your next big flaw. Just be sure you’re only working on one or two at a time. Otherwise, you can quickly get overwhelmed and lose motivation for further improvement. You’ve been warned.

If you’ve been repeating this activity for about 30 to 60 days — the approximate number of days it takes to form a habit — you’ll notice that the same self-awareness you’re generating by making engaging videos will spill into re-attraction as well.

Consequently, you’ll begin to find yourself more observant and in control of your behaviors when conversing with your ex, whether online or offline. And that’s the point. That’s what we’re looking for. That’s how you’ll build a deeper, more meaningful connection with them.

Activity #2: Use Some Statements Instead Of Lots Of Questions

Let’s be honest, you need statements sometimes. After all, enveloping your ex with a bazillion questions can make your interaction a chore. It feels like an interview, fast. And that sucks.

Don’t get me wrong, though. I’m not saying don’t ask any questions — do ask them. I’m just saying that you can still be engaging without asking a ton of them.

So here’s how you can add statements into a conversation where you’d normally ask questions.

• So what was your vacation like?
• Interesting, you never were a huge beach fan.
• Oh, you mostly went to the beach at night?
• That makes sense. You always loved the cold.
• Well, did you generally find your vacation fun?
• Not so much? Yeah, I thought so. You always liked the mountains more.
• You’re probably planning another trip to the mountains to fix the bad taste in your mouth from this one, right?

The true beauty of speaking in statements is that if you do it right, your ex will start asking you questions. And it’s at that point that your date will become much more fun for both of you. So try implementing more statements on your next date.

Activity #3: Talk About Emotions Not Just Facts

Most people just talk about facts. Think of the conversations you have at work when you ask your coworkers how their weekend was. It’s usually just a bunch of facts: “I went riding my bike, I watched basketball, I played with my kids, I bought a new bed framing, etc.”

Conversations like these have very little to do with emotion. There’s not much personal investment on either side. So one way of improving such conversations is by introducing an emotional aspect to them.

Think: how does something or someone make you feel? What emotions specifically does it rise within you? How does it relate to your values and interests? Here’s an example of what I mean.

I went to Miami, and it was wonderful despite the weather being too hot for my taste.

Yeah, what was so interesting about it? What made you go, “shit, that’s so cool?”
Well, Ocean Drive was like in the movies and really surpassed my expectations. I loved the vibe there. I spent an entire evening walking up and down that street, observing everything happening.

What about the vibe made you so excited about that place?
Mostly the people there. They were so easy-going and relaxed and friendly.

That makes sense. I always considered you more easygoing, so I’m not surprised by that statement.
Note that talking about your emotions doesn’t mean you must air them all out until you’re red in the face. That’s a toxic vulnerability, and, as I said at the beginning of this course, it’s unattractive as hell. All I’m saying is that instead of focusing on the “What,” focus on the “Why” of the situation.

Think of it this way. It’s far more interesting to discuss why your ex liked Miami than to discuss what happened there. It’s way more interesting to discuss why your ex dropped out of school than what subjects the curriculum included. It’s way more interesting to discuss why your ex’s new job excites them than the tasks they have to do related to it.

Activity #4: Leverage Jump-Off Points

In every topic of conversation, there are countless opportunities to jump off into other topics. Meaning, there are countless opportunities for word associations to be made. These are your jump-off points. And you should leverage them.

For example, you and your ex could be discussing their recent trip to Japan. And they might say something like, “So we visited Tokyo, and the nightlife there is incredible. We went to this small izakaya and ended up meeting some locals who showed us around.”

This statement is loaded with jump-off points, here are just a few of them:

• Nightlife in Tokyo. You could leverage this jump-off point by asking your ex what was the most memorable aspect of the nightlife or whether or not there was any particular place that stood out.
• Local Experiences. You could leverage this jump-off point by asking your ex about the people they met and what kind of places they’ve shown them.
• Izakaya Experience. You could leverage this jump-off point by asking your ex what the atmosphere was like there or what unique dishes or drinks they tried.

Here’s another example. Let’s say you and your ex are discussing a recent cooking class they’ve attended. So your ex could explain, “The cooking class was amazing! We learned to make pasta from scratch and ended up having a friendly cooking competition.”

As for your jump-off points, a few ideas:

• Pasta Making. You could leverage this jump-off point by asking your ex about whether it’s difficult or not or if they’ve picked up any good secrets or tips about making it.
• Cooking Competition. You could leverage this jump-off point by asking your ex how the competition went and what dishes they made.
• Inspiration. You could leverage this jump-off point by asking your ex who or what inspired them to join the class in the first place and how that source of inspiration perhaps played a role in their life.

You get the idea by now. Almost every statement your ex makes in conversation holds some decent jump-off points that you can leverage to delve deeper into whatever topic you’re talking about and, as a result, build a stronger emotional connection.

Activity #5: Utilize Proper Storytelling

Since human beings are, by default, enrapt by gripping stories, that’s another valuable skill to learn to connect with an ex better. To learn it properly, following a proven story structure is best. The most popular being set-up, content/conflict, and resolution.

Set-up: the set-up is exactly that; you’re setting the scene or the context for what you’re about to say. It’s the foundation of what’s about to be told, and if you don’t set it up properly, then your stories, jokes, and ideas will always seem to be random.

Content or conflict: after setting up what you’ll talk about, you get into the actual content. This can also be the “conflict” in your story. Whatever it is, it’s something that causes tension and expectancy. The content/conflict of your story needs to be intriguing and hook your ex into wanting to know what will happen next. If you don’t build much tension with the content of your stories, you will find them losing interest.

Resolution: the resolution releases the tension from the content/conflict part. Resolutions can come in punchlines (for jokes), conclusions (for ideas), and closures (for generic stories).

As a rule of thumb, never stretch out the set-up or the resolution. Be straight to the point for best results. That said, feel free to stretch the content/conflict as much as you like. Just be aware that it must be gripping throughout to keep your ex engaged. Put another way, it should generate uncertainty or some sort of a dilemma.

Here’s a simple example of a gripping story to illustrate the theory above.

1. Set-Up — I love pizza.

2. Content/Conflict — One day, a friend brought a pizza to my place. It was weird. We didn’t hang out much, I never told him I liked pizza, and he came unannounced. Still… I was hungry, so I took the pizza against my best judgment, thanked him, and closed the door.

3. Resolution — Turned out that the pizza dough was infused with pot. I only found that out after I ate it… And after I tripped balls and almost got arrested for running around town naked.

Activity #6: Lean On Relating

Our next way of connecting is through relating — mutual sharing and connecting over experiences that back up two individuals’ ideas, thoughts, and values. Let’s blast off with an example.

• Let’s say your ex tells you how rude the waiter is.
• Then you say, “Yeah, he was an asshole.”
• Then that word triggers something in your ex, and they come out and tell you how much of an asshole their father was.
• That story then reminds you how much of an asshole your big brother was, always thinking he was smarter than you, always putting you down and treating you like shit.
• You share this with your ex, reminding them of a few strategies for overcoming their father’s wrath.
• Then your ex entrusts you with those strategies, and you share some of yours.
• As you’ve likely noticed, relating goes back and forth like a ping-pong game. You share some specific experiences you had that then illuminate your ex’s experiences and propel them to share them with you, making you more likely to open up even further.

Activity #7: Experiment With Exposing

Exposing piggybacks on our last method. The only difference is the amount of vulnerability you let loose. Here’s an example of what it looks like deployed. Read through it, and then I’ll explain the idea behind it.

• Imagine you’re on a date with your ex, talking about hobbies.
• Your ex responds with how they are taking up new hobbies because they’ve lost interest in the old.
• You go a bit deeper and ask them what was wrong with the old hobbies.
• They tell you they all had to do with partying and drugs, and that’s just not who they want to be anymore.
• You respond with a story of how immature you were as a teen, how you recently made that realization, and how your life is better for it.
• Then they ask you why you even got into that lifestyle.
• Then you say it was a form of escapism. You felt worthless and thought the only way to be perceived as cool and of high social status was by drinking and partying like a mad lad.
• Then your ex tells you how they were in the same boat and that the reason for their feelings of inadequacy was their parent’s recent divorce.
• Then you tell your ex about your childhood trauma — being bullied throughout primary and middle school and how that made you think of yourself as unworthy.
• And now you’re discussing your childhood traumas, your memories, the meaningful experiences you had, how you’ve grown as people, how you changed, what you’ve left behind, and so on.

What you’ve done here is went from talking about mundane hobbies to dissecting and connecting over shared childhood trauma and deep-seated self-esteem issues. When done artfully, these conversational spirals can deeply bring two people together — not just emotionally but even sexually and spiritually.

Just keep your expectations realistic. These types of conversations usually don’t go as smoothly as in the example I shared. They also don’t drift from point A to point B so quickly. You’ll often come to the deep stuff after about 30 minutes to an hour of talking and relating with your ex. It’s a progression — and a rather slow and subtle one at that.

Activity #8: Put In All Together Through Improvisation

This is the only activity from this article that you can easily do alone. It’s also probably one of the most important ones because it takes all the previous ones into consideration as well. Here’s how it goes.

Below is an embedded random word generator app. Click on the big, shiny, red button to receive a random word. Then I want you to speak about that word for at least 60 seconds without stopping.

Try to be as creative as possible when you do this. For example, the word “apple” could refer to the fruit, the tech company, Newton’s discovery of gravity, the poison apple from Snow White, the record label “Apple Records,” and so on.

As you’re improvising based on the random words, try to gradually implement the activities we covered till now, one by one: try to notice how you come across while speaking, use statements in addition to questions, talk about emotions and not just facts, play around with jump-off points, storytelling, relating, exposing, and so on.

Be sure you implement only one or two activities at a time. Otherwise, it can quickly get overwhelming. Finally, after a few days, when you feel comfortable with improvising, use the word generator to write down five separate one-paragraph stories that incorporate at least half of the previous activities you went over.

See the Pen
Random Word Generator by Max Jancar (@Max-Jancar)
on CodePen.