Stop Obsessing Over Outcomes to Improve Dating Confidence

Written by dating coach for men Gary Gunn - Founder of Social Attraction

3 August 2025

Being obsessed with the outcome in your dating life is not only ruining your self-confidence, it’s also ruining your results. I understand what it’s like when you’re feeling low in your dating life and want to start meeting and attracting more women, but you don’t know why you’re stuck. What often happens is you get caught in a cycle where you become more and more obsessed. Then, when you finally meet a woman you like, the desperation takes over.

You can cut out a lot of issues in your dating life by stopping chasing the outcome. If I’ve said this once, I’ve said it a thousand times. If you want to improve dating confidence, you have to throw away the outcome and focus purely on skill acquisition.

Table of Contents

Why Focusing on Skills Improves Dating Confidence

Let me give you some examples to make this clear. Today, I’m coaching one of my clients in an art gallery in central London. I’m helping him learn how to tell engaging stories. Yesterday, we worked on story structure, so he now knows how to avoid wasting words and get straight to the point. But what about delivery?

Delivery is how you bring excitement and joy to your stories. Here’s an example. Let’s say I’m telling a story just to attract women. I might say something like:

“Um, yeah, so I saw an altercation in the street, realized I didn’t know how to defend myself, so I ended up spending a year and a half learning martial arts.”

That sounds like I’m just going through the motions. You don’t really understand much about me from the way I spoke.

The Power of Emotion in Storytelling

Today, I’m working on helping my client bring more emotion and enjoyment into the process of telling a story. If you enjoy telling the story and tell it with the right story arc, it will be well received.

Here’s the same story with more feeling:

“It was early in the morning, around half six. I’d just woken up and come for a decaf coffee before coaching. So, I saw one of my friends get assaulted in the street. It was one of the worst things I’ve ever seen. My friend could take care of himself, but it made me realize I didn’t know how. After some thought, I decided I needed to sort this out. I found an amazing martial arts instructor who rarely takes on clients. It took me a while to convince him, but once he agreed, it was one of the most incredible experiences of my life. We trained every day for about a year and a half. I not only learned to defend myself but enjoyed the journey of learning one-to-one with him. So much so that I forgot why I started training and just embraced the process itself.”

This story uses the same problem, action, result structure but feels more alive because it shares emotion. When coaching people, this is where many guys struggle. They get the structure right but tell the story like they are going through the motions. This makes the story dull and boring.

Is Improving Your Dating Confidence Worth the Effort?

You might ask, “Isn’t this a lot of effort just to attract women?” The answer is yes, if that is your only reason for learning these skills. If you only learn to attract women and get results, you are outcome focused. That creates pressure and often frustration.

I understand this is difficult because you want success in your dating life. You want to improve dating confidence, but I’m telling you not to focus on the outcome. When I struggle in an area of my life, I set a goal and then figure out what skills I lack to achieve it.

For example, if I want to run 100 meters faster, I don’t just focus on running faster. I focus on technical skills like stretching, rolling, running technique, and training. Then I make a plan and focus on that plan to acquire the skills. The outcome takes care of itself.

How Focusing on Outcome Creates Anxiety

If you struggle in your dating life, it’s often because you’re putting too much pressure on yourself and chasing outcomes. When you focus on outcomes, you create anxiety and desperation. This affects your confidence and your results.

When coaching clients, I offer two approaches. One is an intensive course that teaches how to approach and speak to women in everyday life. This helps overcome fear in a few days. Overcoming fear fast makes a big difference. Many clients find this all they need.

The other half want to focus on skill acquisition. This takes longer and involves changing habits over time. It can be frustrating if you only focus on results and ignore the process.

Elongate the Process to Improve Dating Confidence

One thing I tell clients is to elongate the process in their minds. If you want to learn how to approach women, that can take a weekend or a few days. But for deeper growth, give yourself a year.

Set a goal like, “By the end of this year, I want to be in a healthy relationship with a woman I’m attracted to.” Then work on the skills steadily.

If you try to do that in three days, you will get stressed and chase outcomes. But if you give yourself too much time, like five years, it’s too long. The sweet spot is a time frame where you feel relaxed about achieving the goal.

For example, if you are 50 and never had dating success, three months is too soon. Give yourself a year. If you are recently divorced and confident, three months might be fine.

Avoiding False Deadlines to Reduce Anxiety

This principle applies to all areas of life. If you invite a woman on a date for Friday and text her Monday with no response, anxiety kicks in because you are chasing a deadline you don’t control.

To avoid this, invite women to something you are already doing. For example, my client has a date at the Tate Modern gallery. He’s already going, so she just meets him there at 2:00. If she cancels or is late, he doesn’t mind because he is going anyway.

Also, avoid open-ended deadlines. Instead of saying, “Let me know if you want to come,” say, “Let me know by midday tomorrow.” This shuts down the cycle of insecurity while you wait.

How False Deadlines Damage Your Dating Confidence

When you place a deadline on getting a text back or a yes to a date, you create anxiety. This feeling comes from uncertainty and a lack of control. Anxiety kills confidence and causes you to chase the outcome even harder. That chasing behavior lowers your attractiveness and makes you less confident in your dating life.

By removing false deadlines and setting clear boundaries, you protect your confidence. This keeps you relaxed and helps you perform better naturally. If you’re calm, you will be more attractive and feel better regardless of the outcome.

The Importance of Skill Acquisition Over Instant Results

I’m about to start an acting class at the Royal Academy of Dramatic Arts in London. Even though I teach storytelling and have done so for a long time, I’m self-taught. I’ve practiced and drilled in real-life situations, but I haven’t had formal training in acting.

This next step in my life is about expanding my skills. When my client first signed up with me, his goal was just to learn how to approach women. Because he learned that fast, he moved on to wanting to improve his storytelling.

This is a powerful life lesson. When you outgrow your current situation, you naturally focus on what’s next. That’s why focusing on skill acquisition is so important. You can’t expect to improve dating confidence or success by only knowing how to approach women.

You have to go deeper — learn how to tell stories, flirt, connect, tease, and so on. These are skills that build on each other. If you don’t master the skills, your attempts will be clumsy, women lose interest, and frustration builds.

Give Yourself Time to Grow and Improve Dating Confidence

When you go through any growth or change period, give yourself enough time to understand the process and do your homework. Growth takes patience and consistent effort.

I want to stress this: I can coach you in person or online all day long, but if you don’t do the homework between sessions, your results will be limited. If you just sit at home and watch TV or focus only on work, you won’t see the change you want.

You have to invest in coaching AND be willing to put effort into practicing new skills in real life. That is the only way to improve dating confidence and create lasting change.

Why Outcome Obsession Limits Your Success

When you chase outcomes alone, you become obsessed with getting the results instead of developing your skills. This obsession causes stress, desperation, and blocks your growth.

Focusing on skill acquisition lets you relax and enjoy the process. You get better naturally and confidence grows. The outcomes will follow as a natural result of your growth.

Summary: Improve Dating Confidence by Focusing on Skills

To improve your dating confidence, stop obsessing over results. Focus on developing skills step-by-step and give yourself realistic time frames to grow. Remove false deadlines that create anxiety and pressure.

Invite dates to activities you already enjoy to take the pressure off. Practice storytelling, approaching, and connecting with women in a way that feels natural and fun.

Most importantly, commit to doing the work outside of coaching or training. Skill acquisition takes time, patience, and effort but the payoff is real confidence and lasting success in your dating life.

How to Avoid Chasing the Outcome in Your Dating Life

Chasing the outcome in dating is a common trap that lowers your self-confidence and ruins your results. When you obsess over getting a date, a reply, or approval, you put too much pressure on yourself. This pressure creates desperation, which is easy to detect and turns women off.

Instead, focus on the skills you can control, like how you approach, how you tell stories, and how you build connection. When you shift your attention to mastering these skills, your confidence naturally improves.

This shift is not easy, especially if you’ve been stuck in a cycle of chasing results and feeling low. But it is essential if you want to improve your dating life and become more attractive without forcing outcomes.

Practical Example: Storytelling to Build Confidence

Let me give you a practical example from my coaching sessions. Yesterday, I worked with a client on storytelling structure. He learned how to avoid wasting words and get to the point quickly. Today, we’re focusing on delivery — the emotion and excitement you bring when telling a story.

For example, a flat story might be:

I saw a fight on the street. I realized I didn’t know how to defend myself, so I spent a year and a half learning martial arts.

This version is boring and doesn’t reveal much about you. It lacks emotion and personality.

Now, here’s the same story with more feeling and delivery:

One early morning, I saw a friend get assaulted in the street — one of the worst things I’ve ever seen. It made me realize I didn’t know how to protect myself. So, after some thought, I found an amazing martial arts instructor. It took a lot of convincing to get him to train me, but it was incredible. We trained every day for a year and a half. It wasn’t just about defense — it was a journey of learning and growth. I even forgot why I started training and just loved the process itself.

This second version connects emotionally. It shows growth and passion, making it much more engaging. When you practice telling stories like this, you build confidence naturally because you’re sharing more of who you are.

Why Enjoying the Process Beats Outcome Fixation

When you enjoy the process of telling stories, approaching women, or flirting, your energy changes. You become more authentic, relaxed, and confident. This positive energy attracts women far better than desperation or trying to force a specific outcome.

If you only focus on the end result, you risk burning out or becoming discouraged if things don’t happen quickly. Skill acquisition requires patience and consistent effort over time.

Setting Realistic Goals to Improve Dating Confidence

A key step is to set realistic time frames for your dating goals. Don’t expect overnight success. For some, a year is the right amount of time to make meaningful changes. For others, three to six months works.

Choose a deadline that feels relaxed enough to avoid pressure but focused enough to keep you motivated. The goal is to give yourself enough time to develop skills and habits without obsessing over quick results.

How Deadlines Affect Your Dating Confidence

Deadlines can create unnecessary pressure if they’re too tight. For example, if you ask a woman out and she doesn’t reply quickly, you might start feeling anxious and insecure. That anxiety comes from the uncertainty and the “deadline” you’ve set in your mind.

One way to reduce this pressure is by inviting women to things you’re already doing. For example, if you plan to visit an art gallery on Friday, ask her to join you there. That way, if she cancels or doesn’t show up, you’re not stressed because you were going anyway.

Also, giving her a reasonable time frame to respond helps close the loop. Saying something like, “Let me know by midday tomorrow if you want to come” prevents endless waiting and helps you stay in control of your emotions.

The Role of Skill Acquisition in Lasting Change

Quick fixes like weekend boot camps are great for overcoming initial fears, like the fear of approaching women. But lasting confidence and success come from ongoing skill development.

Many of my clients want to improve different areas over time. One might start with learning how to approach women, then move on to storytelling, flirting, or teasing. This gradual skill acquisition is how real growth happens.

Trying to rush through all these stages can backfire. You’ll come off clumsy and unsure, which only hurts your chances. So it’s important to embrace the journey and be patient with yourself.

The Importance of Doing Your Homework

Coaching and training provide the tools, but the real results come from the work you do outside of sessions. If you don’t practice, don’t apply what you learn, or don’t change your lifestyle, you won’t see progress.

Think of it like learning a sport or musical instrument — you can’t just watch the lessons and expect to be great. You have to train regularly, put in the effort, and stay committed.

This homework mindset also shifts your focus away from chasing outcomes. Instead, you focus on developing skills, which naturally leads to better dating success.

Outgrowing Your Current Situation and Moving Forward

Another important part of building confidence in dating is recognizing when you’ve outgrown your current skills. For example, one of my clients started just wanting to learn how to approach women. He picked that up quickly, so then he shifted his focus to storytelling.

This is a natural process. As you master one skill, you become ready for the next challenge. Whether that’s flirting, connecting on a deeper level, or teasing playfully, it’s all about gradual growth.

Trying to skip steps or rush the process usually leads to frustration. Developing real confidence means being patient and committed to this ongoing journey of skill acquisition.

How Long Should You Give Yourself?

Setting realistic timeframes is key to avoiding frustration and chasing outcomes too hard. If you’ve never had much dating success and you set a 3-month deadline, it can create unnecessary pressure and insecurity. Instead, giving yourself around a year can be more relaxed and sustainable.

On the other hand, if you have experience and confidence but want to get back into the dating scene after a break, 3 to 6 months might be enough.

The sweet spot is when you feel relaxed but still motivated. Too short and you feel rushed, too long and you lose focus. Find the right timeframe for you and commit to consistent work during that period.

Managing Anxiety Around Deadlines and Uncertainty

Deadlines can cause a lot of stress, especially when combined with uncertainty. Imagine you’ve invited a woman out for a date on Friday. You text her Monday, and she hasn’t replied yet. Suddenly, anxiety creeps in because you don’t know what’s going to happen.

This kind of uncertainty triggers stress because your mind creates a false deadline. You feel like you must get an answer right now or risk missing out.

One way to reduce this anxiety is to invite someone to join you for something you’re already planning to do. For example, if you’re visiting an art gallery, invite her to meet you there at a certain time. If she’s late or cancels, it doesn’t affect your plans. You’re already committed to going, which takes the pressure off.

Adding a clear deadline for her to respond, like asking her to let you know by midday, also helps. It ends the waiting game and frees you from the cycle of insecurity.

Embracing the Process and Avoiding Outcome Obsession

When you go through a dry or difficult period in your dating life, it’s often because you’re chasing the outcome too hard. You put too much pressure on yourself and try to force results. This leads to frustration and can even push people away.

The best way to break out of this cycle is to focus on enjoying the process itself. Instead of obsessing over getting a date or a relationship, put your energy into building the skills that will naturally lead to those outcomes.

For example, I’m currently booking onto an acting class at the Royal Academy of Dramatic Arts in London. Even though I teach storytelling, I want to deepen my skill set with professional training. This is an important mindset: you outgrow your current level and then move on to the next step.

Skill acquisition is a journey. When my client first started, his goal was just to learn how to approach women. After mastering that quickly, his goal shifted to storytelling because he realized that’s the next essential skill.

The Importance of Skill Acquisition in Dating Confidence

The truth is, developing true dating confidence comes down to mastering a series of skills step by step. First, you learn how to approach women without fear. Then you learn how to tell engaging stories. After that, you focus on flirting, connecting on a deeper level, and even teasing in a playful way.

Skipping steps or rushing through this process often leads to awkward interactions and frustration. Women can sense when you’re clumsy or desperate, and that can cause them to lose interest quickly.

That’s why it’s so important to give yourself enough time to truly learn and practice each skill. Skill acquisition is not a quick fix — it’s a gradual transformation that builds lasting confidence from the inside out.