I Spent Over $10,000 on Dating Coaches to Find Love — 7+1 Lessons Learnt

I spent over $10,000 on relationship and dating coaching — looking at that figure on paper, it seems pretty wild.

Being single and looking for love can be a pretty expensive business. I stumbled upon various articles outlining the hidden costs of being singles — things like not splitting rent and bills etc. And that’s no joke. However, on top of that, you need to add dating apps subscriptions, dates (those drinks, coffees and restaurants ain’t going to pay themselves) and not to mention dating coaching.

The first time I signed up for relationship coaching was in the aftermath of a pretty painful breakup. The goal of those sessions was to let go and heal.

The second time around, I decided to take on dating coaching with the specific aim to navigate the world of online dating — hopefully with minimal collateral damage. And that’s when things got reeaally expensive.

Although expensive, shortly after trying out my way, I thought I could use some help. I had never “dated” before — my previous relationships mostly came organically from friends of friends, ex colleagues, university etc.

I had zero experience with online dating — and being an introvert, it seemed pretty daunting.

After giving a bit of background, here some of the lessons I learned after spending over $10,000 on multiple relationship and dating coaching, what has worked for me and what I was doing completely wrong.

If you are still reading I guess you want to know one thing: was it worth it or was it a waste of money? Did I find love?

Let me get there but yes, it was worth it. I made it work, and worth it — I put in the work and trusted the process, even when I felt lost and hopeless.

1 — I rolled up my sleeves and got ready for some work - both before and while dating

Mistake #1: previously, I did not want to put an intentional effort in the process .

Dating requires effort, but so does a relationship — if finding a meaningful connection and love is our priority, then we should act accordingly.

I know there are so many things competing for our attention at any given moment of the day (career, family, friends, administrative tasks, selfcare etc) but if we want to find (and maintain) love, then we need to be ready to make time for it.

To start with, I tried to do something small every day in the direction of finding love. This does not necessarily mean going on dates every single day but just trying to put in a little effort in any form — reading a book or listening to a podcast on a relationship topic I find relevant; spending some time on a dating app (even when I only wanted to watch Netflix); speaking with the people I connected with; not being constantly on my phone and be open to potentially strike a conversation irl etc.

Taking small steps every day is important not just because the “Butterfly effect” might have some applications in very context, including dating (a simple way to think of it, it is the idea that seemingly small, trivial actions might ultimately result in something with a much larger impact) but also because it is a powerful signal — It was my way to show commitment to myself.

Also, I put myself out there.

Have you heard of dating challenges? Like 30 dates in 30 days — they are now super trendy in TikTok, Instagram etc.

I decided to take on a dating challenge of my own, which was quite hard at times, especially considering I have a demanding full time job, side projects etc. I will not elaborate on how I did it here, though I’d like to write about it in the future (in case helpful to anyone also juggling long hours).

It’s important to note that the 30-day challenge doesn’t require you to go on 30 dates in a row. Instead, it’s about setting goals and sticking to them.

Additional to the work and effort in the dating phase, some of us can benefit from a bit of prep work ahead of dating.

Such prep work can be a game changer — it was for me.

I took a 6 week “dating ban” with a therapist, while I would not be dating, focusing on myself in preparation of dating. It was such a relief and helped me get in the right mindset for when I eventually started dating. I used this time to work on my “dating plan” (I touch upon this in the next section), while assessing my relationship history and identifying dating patterns.

If you notice certain patterns in your dating life (ie attracting unavailable men, getting into toxic relationships, self-abandonment ) then you might consider talking to a professional, even just to get some insights.

2 — I created a dating & love plan

Mistake #2: I used to think love should come naturally and did not want to “plan” nor “force” anything.

Having a plan is often considered vital in various aspects of one’s life — yet when it comes to dating, having a clear plan is not the norm.

A love plan gave me structure and direction, while helping me feel more at ease with the process.

It is beneficial to anyone, but in particular to those struggling with boundaries and people pleasing (I know something about it!).

In my love plan, I set a clear idea of what I was looking for in a partner and defined the type of relationship I wanted, what my needs and boundaries were in all the different stages of dating etc.

It is not a “one-size-fits-all” approach — it is highly tailored to what each person wants and needs.

Some examples of things to include — details on your potential partner (things you value and non-negotiables, expectations, lifestyle choices etc); practical dating timeline (how many days of consistent communication before a first date; how many dates in public; how long before you feel comfortable kissing/intimacy at various levels etc — it can be X dates/weeks or until you are exclusive/discussing commitment — whatever feels comfortable with you! ..etc etc).

It is probably ideal to create such love plan before starting dating — so that you set your “rules” based on you without being conditioned by specific people, circumstances etc.

Having boundaries and listening to yourself becomes 100 times harder while being in an emotionally charged situation — ie when you are already dating someone you might like.

3 — I subscribed to the idea that “Authentic beats likeable”

Mistake #3: I wanted to be liked, at all costs. Validation felt good — especially from potential romantic partners.

Once realized that, I adopted a radical (and uncomfortable at first) shift.

On a first date (and the subsequent ones!), the goal I set for myself was to be authentic, rather than being liked.

I thought:

“If you are authentic and goes well, good for you — you win”

“If you are authentic and it doesn’t go well, then it is fine too — you win”

“If you are not authentic and the other person ‘likes’ you — you lose”

I did not want to be liked for someone I wasn’t.

It happened in the past and I was committed to saving myself the heartache.

If you are an empath, then you might be able to intuitively read the other person and know what to do or say in order to get them to like you.

However, this doesn’t benefit either of you — it is hurting your chance to find meaningful connections elsewhere (for both of you).

4 — I realized that if I am with Mr Wrong, I can’t be with Mr Right

Mistake #4: Rejection was the ultimate enemy. I hated being rejected and I hate rejecting people. It just seemed painful.. and mean.

Quite the opposite, rejection is medicine in dating and I truly started believing the mantra “Rejection is protection”.

I took a good look at my exes and realized that for most of them I was definitely happy it did not work out, ranging from “what was I thinking?!” moments to the simple realization of pretty fundamental incompatibilities.

Dating involves a good amount of inevitable rejection — it is a key ingredient of the mix and I had to learn how to handle that graciously.

I realized that being single doesn’t hurt my chances of finding love. Being with the wrong person does, obviously.

5 — I started to watch for my speed limits — and slowed down

Mistake #5: I loved to be swept off my feet — it felt romantic! And often decided to ignore some warning signs (even if “just” incompatility).

When I first meet someone I like, I sometimes idealize that person. It can happen and I (no longer) judge myself for it, I just take my time.

With time, people show their true colors and you will have the chance to see how they respond to different situations.

Also, it will give you the chance to see how they react to issues that *you* may have — are they supportive? Are their reactions in line with your needs and expectations?

People tend to be on their best behavior in the first phase of dating— even if you commit yourself to being authentic, you don’t have any guarantee that the person you are dating is doing the same. They might have their own agenda, or maybe they just like you and want to be liked back.

In my experience, slowing down (and not overcommitting too soon) proved to be a powerful ally when it comes to wide range of issues such as idealization, love bombing and ghosting, in the first phase of dating.

Also, without playing games, I started giving the other person the chance to step up and show up for me. If you need their support or just want to share something difficult for you, be vulnerable and see how they respond.

I raised my standards but lower my assumptions — I became an attentive observer of how they behaved and responded, in time.

6 — I learnt how to be more patient with myself

Mistake #6: I used to get very impatient with myself, if I wasn’t getting the results I wanted, when I wanted.

Reality is.. It is normal to experience some dating fatigue.

Dating implies a good amount of inevitable rejection, it is uncomfortable and it can be tiring: you need to manage time, energies and emotions while probably juggling a full time job/ studying/ family commitments..

Allow yourself options and know that you are in control.

If you get to the point where you feel anxious and overwhelmed at the idea of dating, you might even decide to take a break — give yourself some weeks or a few months to focus on yourself and get your energies back — I have myself benefited from a break from dating, at a time I felt completely depleted and emotionally drained.

7 — I stopped playing it cool

Mistake #7: I preferred keeping my cards close to my chest.

Over time, I learnt that being vulnerable is uncomfortable but it is often worth it.

If you are looking for a partner and love (and maybe someone to build a family with), say that — sooner, rather than later (my stance is — do it right away! First date or earlier, while texting).

Keep it positive and smile confidently while expressing that, because it is a beautiful thing!

If the other person wants something casual, be grateful as they are being honest and you can direct your energy elsewhere, saving yourself time and a lot of guessing.

FINAL BONUS: Ending on a cheesy note — I learnt the power of loving myself and keeping investing in ME

I learnt that learning to love yourself takes time and effort, but it is the best foundation for a sound relationship.

If there is one thing you want to invest on — this is it, before anything else.

If you are committed to loving yourself, people will automatically respond to that.

Loving yourself means protecting yourself, knowing your needs and knowing your needs deserve to be met. Try, it is like building a muscle. If you want help, you can try coaching (not necessarily relationship coaching) and therapy, if not there are thousands of books and courses.

Oh I almost forgot. Did I find love? Yes, I did.

And I believe all the inner work positively contributed — I can clearly see how I learnt to break some old patterns.

It was an incredibly challenging process (and not linear!). However, I am happy and grateful I put in the necessary time and energy.

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I would love to hear any other dating lessons you learnt in your journey below in the comments 💬!

Ps: this is my first Medium story 📖— I am a new writer and still figuring it out, your support means a lot — feel free to follow/share/and save this story to your lists!

If you want, check out my other article on dating and money:

https://link.medium.com/aW8JTlsrAzb