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Fear of Dating Rejection Keeping You Stuck? Read This.

How I Went From Crying Over a Boy I’d Been On Two Dates With to Forgetting He Even Existed . . . And How You Can, Too.

Let me tell you a story about the time I cried big tears over a guy I’d only been on 2 dates with.

The story starts with me locking eyes with a tall, dark-haired lawyer in my local coffee shop in Washington, DC, where I usually worked on my grad school admissions essay. 

I was instantly smitten. 

He was tall, he had dark hair, piercing brown eyes, and he was wayyyyyy older than me: he was, in fact, a lawyer to my student, and he had a JOB as a lawyer in a real law firm (which I felt like was the epitome of adult and grown-up cool). 

I was SO into it. 

He asked me out, and OF COURSE I said yes.

We went on two (honestly kind of mediocre) dates, and then he dumped me over text message. 

I was devastated.

After he dumped me, I sobbed on the phone to my mom over a bar of chocolate and a glass of wine. I then went on a long run (the OTHER thing that I no longer do these days, other than crying on the phone over a boy I’ve only known for 2 weeks, is run), where I cried harder every time I saw a dark-haired man in his mid-30’s and despaired that I would probably never find love again.

I was CERTAIN that it meant something terrible about ME that this guy had rejected me.

I felt like I must not be pretty enough, sophisticated enough, interesting enough, or grown-up enough to date this guy.

I also thought that he was the LAST 30-something year old DC lawyer who would ever try to date me again, and that I’d missed my only chance to date a “real adult” (boy, was I wrong!).

I also thought that him not dating me meant that I MUST BE undesirable to men (wrong again on that front!).

I was a mess.

But then — surprise! I did what I thought I was never going to do: I got over it.

Over coffee and scones the next day, my friend Chanel pointed out that the man I was crying over was a 35-year-old lawyer who was applying to medical school at a cafe (which is how I’d met him) which meant that . . . he wasn’t at work. (Why wasn’t he at work?) She also pointed out that this guy had told me on numerous occasions that he didn’t have many friends in DC, and that’s why he was at the coffee shop so much.

This was when I realised that I was crying over a guy who was unemployed, had zero friends, and was probably only attempting to date 22-year-olds because all of the women his age would expect to date a guy who had, you know, his life (at least a little bit!) together.

And that, in being dumped by this man, I probably actually had dodged a massive bullet.

Young and starry-eyed Chelsey had thought that it was ✨ destiny ✨ that we were always at the same coffee shop at exactly the same time, when the reality was that actually — the reason we were always at the same coffee shop at exactly the same time was that this guy was a grown man who didn’t have a real job. 

Thank goodness for my friends who, at the time, told me what I didn’t want to but needed to hear.

The reason I am telling you this story is that I learned a lot about rejection from my experience with the Unemployed Lawyer. 

I am going to teach you what I learned so that you can save time and avoid feeling sad over a connection that isn’t worth your tears.

Here’s what I learned. 

1: Know that they aren't rejecting YOU.

Here’s the thing: Before we’ve actually MET somebody (ie, before the first date), they aren’t actually rejecting US.

The truth is that most people don’t know how to present themselves well online, and that their dating profiles don’t do a good job at representing them as the whole, interesting, unique people that they are.

Before we’ve actually met somebody, what they’re REALLY rejecting isn’t us: they’re rejecting our bad opening lines, our lacklustre texting skills, or our less-than-flattering Tinder photo. Not US as people. 

Essentially, they’re rejecting our dating STRATEGY.

Now, you may not think that you have a dating strategy, but everyone has a dating strategy. If you have a dating bio, you’ve thrown a couple of photos up on Hinge, or you’ve ever sent a text asking someone out — guess what? You have a dating strategy.

And if you’re getting rejected often in the early stages of dating — know that yours isn’t working for you.

The good news is: You can take heart in knowing that your whole, unique self isn’t being rejected in these encounters — only your first impression.

The other good news is: You can change your dating strategy! Strategies are fixable. We can learn to improve our pickup lines, to get better at texting, and to pick a better Tinder photo. These skills are not the real “us” — they’re just skills. And, like all skills, they can be improved.

2. Stop the story.

Human brains are meaning-making machines. Our brains make up stories all day long about the things that happen to us and what they “mean” based on our memories, our worldview, our values, and our life experiences. 

As soon as we experience something, our brain goes to work to contextualize this experience and figure out what it all “means.”

Our brain can’t NOT make up stories.

Stories are how we make sense of the world.

Because our brain doesn’t like uncertainty, when we don’t know something, our brain will usually try to fill in the gaps with a story.

Sometimes these stories are accurate, but just as often they AREN’T accurate: they’re just stories.

So let’s take a look at how this applies to rejection.

When we experience rejection, there’s a lot of uncertainty. We cannot possibly know for certain why somebody rejected us. 

But — remember, our brain doesn’t LIKE uncertainty. So it’s going to make up a story to fill in the gap. 

Unfortunately, what our brain usually fills the gap with are our fears, our worries, and our darkest thoughts. Unchecked, our brain will usually tend to decide that what this particular rejection “means” is that we’re bad, or we’re wrong, or that we’re incapable of finding love.

Just like I had decided that the Unemployed Lawyer was my last chance at finding love (he wasn't), your brain is wired to fill in the gaps of why you just got rejected with your deepest fears about being alone forever, or flawed, or having 15 toes and a horn growing out of your forehead, or whatever.

But here’s the thing: Our stories about rejection are just stories. Like your fears about having a horn growing out of your forehead, they aren’t true.

At ANY stage in the dating process, rejection doesn’t actually mean anything about our worthiness or our capacity for connection and love. It doesn’t mean that nobody will ever love us, or that we’ll never find our person.

What rejection ACTUALLY means that we either didn’t impress a stranger, that our dating strategy isn’t working for us, or that we aren’t a good match for somebody. Dating rejection is just a sign that there’s an incompatibility between two people. Nothing more.

It’s okay to feel disappointed by rejection. But when we make it mean more than it actually does, we hurt our own feelings. 

The only time that rejection means that we won’t find love is when we decide that it means that, and we give up on dating. 

Our person is out there, and we won’t find them if we give up.

So — what do we do, then?

We can’t stop our brains from making up stories, but we CAN choose to take a magnifying glass to the stories we make up and to critically evaluate whether we want to subscribe to that story, or whether we’re going to choose a different meaning.

In the case of rejection, our job is to not buy into the scary stories our brains make up, but instead to INTERRUPT those stories and intentionally choose to create a DIFFERENT story: To choose to believe that rejection is just a sign that we weren’t right for somebody (and that they weren’t right for US!). 

3. Have a plan.

Thinking about dating in terms of strategy is KEY to overcoming the fear of rejection.

When we’re diving into dating without a plan or a strategy, rejection is going to feel FAR more personal — because we only have ourselves to point the finger at when we strike out.

Thinking about dating in terms of strategy changes all that. When we start thinking about rejection as feedback about our dating STRATEGY, rather than about US, we can start to troubleshoot where our dating efforts may have gone wrong. 

When we think about dating in terms of strategy, we can depersonalise rejection: we can look at what our dating results (or lack thereof) have to tell us about where our STRATEGY is and isn’t working, and how we can improve it. Instead of looking at ourselves and thinking that WE need improving, we can look at our dating STRATEGY and build out dating systems optimised for getting the results we want.

Rejection then becomes an important tool for evaluating our dating strategy. It can help us to figure out what’s working for us and what isn’t, and it can show us what parts of our strategy need to be improved.

By thinking about dating in terms of strategy, rejection becomes our ally, our barometer, and our secret weapon for dating success.

4. Treat dating like one big science experiment.

Here’s the thing: I love you, but . . .

You’ve GOT to stop going on dates and then getting all sad and upset when the person on the date isn’t your soulmate and THEN giving up on dating altogether because you think it’s a “waste of time” and you’re probably never going to find love.

Really, truly. This pattern is holding you back, BIG time.

The truth is: Not everyone is meant to be your soulmate.

When you turn every date into this big make-or-break event, when you believe that every date NEEDS to end with you meeting “The One” or else the date was a waste of your time: you’re putting a LOT of pressure on yourself that doesn’t need to be there and that makes dating feel WAYYY harder than it needs to feel.

At its simplest, dating is just an opportunity to learn more about who YOU are, what YOU’RE looking for, and how to get it.

Yes, it’s also an opportunity for people to get to know YOU and to figure out if you’re a match for them, but the reality of compatibility is: you WON’T be a match for everybody. And not everybody will be a match for you. And that’s totally okay.

Remember, rejection is just somebody deciding that we aren’t compatible enough to be a match. Nothing more.

It’s not possible that we’re going to be a match for every single person we go on a date with — can you imagine how stressful that would be? You would literally need to sort through thousands of potential boyfriends, and you would never feel confident that you were making the right decision! 

The truth is: MOST people on dating apps aren’t going to be a good fit for you, and you won’t be a good fit for them.

That’s just dating.

Instead, here’s what I want you to do: I want you to treat dating like a big science experiment.

Dating like a scientist turns rejection into your new BFF.

Instead of seeing every date that ends in rejection as a total bust, I want you to start seeing dates that don’t end with you meeting your “person” as the NORM. I then want you to start thinking of every date you go on as a little EXPERIMENT that teaches you about you, about what you’re looking for, and about what you need to do to find it.

When we experiment, we try new things, we’re willing to make mistakes, and we’re eager to learn from our mistakes to find out how we could do things differently next time. When we experiment, we happily engage in trial-and-error and we’re willing to pivot a few times until we’ve found what works for us.

The same can be true for dating. 

Here’s an example: Let’s say we go on a date with someone we think we really like. They’re funny, they’re cute, and they have the BEST dimples.

Now let’s say we’re home from our date, and as we sink into our couch with a glass of wine, we get a text that reads: “I really enjoyed our date, and I think you’re a lot of fun. But I just don’t think that we’re a match because I’m looking for someone who also doesn’t want children. Good luck with dating.”

Now, we might have previously gotten really upset when we got this text. We might have even blamed ourselves, and maybe we would have even, in a moment of frustration, sworn off dating forever.

But, because we’re now treating dating like an experiment, what we’re going to do NOW is we’re going to choose to see this response from our date as FEEDBACK.

Not as feedback on OURSELVES, but as feedback that tells us A) what we’re NOT looking for in a partner and B) what we need to do to find what we ARE looking for!

We now know that somebody who doesn’t want children may not be the best match for us, especially if we really DO want children.

We also know that our current dating strategy to find people who ARE what we’re looking for (somebody who, like us, also wants children), isn’t working for us.

We also have some idea about what to do next: We probably need to take a look at our dating profile and figure out what we need to change about it to communicate clearly and quickly that we DO want children. We want to make sure that our stance about children is clear enough upfront so that, going forward, we don’t waste time commuting to a date, energy texting back-and-forth, or emotional bandwidth getting all excited over somebody who doesn’t want the same things we do. 

Just like my experience getting dumped by the Unemployed Lawyer, our date’s rejection could be a blessing that helps us find the right partner faster.

A failed date is just data.

The gold is found in how we USE that data to be successful on our next one.

5. Jump in the pool.

The hardest part of jumping in the pool is taking the leap.

Once we’re IN the pool, the cold water actually feels pretty good on our skin, and our bodies adjust. But taking the leap is the scary part.

If we’re avoiding dating because we’re worried about rejection, the BEST thing we can do for ourselves is to jump in the water and get started. We can get used to cold pool water — and once we’re in it, we can have a lot of fun. But getting over our initial fear of rejection and taking the leap is the prerequisite to getting the thing we want: healthy, fulfilling, passionate relationships.

As my uncle always said: “To play the game, you’ve got to be IN the game.”

The only way to figure out how to be successful at something is by getting out there and DOING. Not by thinking about doing, not by endlessly preparing, and not by reading a million self-help books. 

When we wait to feel “ready,” we convince ourselves that if we’re perfectly prepared, we’ll be able to avoid the thing that feels scary. But we’re never going to completely rejection-proof dating, so if that’s what we’re waiting for, we’re never going to be “ready.”

DOING the scary thing is how you figure out whether what you’re doing works or doesn’t work. If you get rejected: GREAT! You’ve learned something. You can now take that new information and use it to iterate your dating strategy. You can go back and make changes and make your strategy better so that you CAN succeed in the future.

But if you never start, you’re never going to get to the part where you’ve found what works and you’re succeeding. If you don’t start, you’ll miss out on a lifetime of love and companionship because you were afraid to play the game. You’re guaranteed to lose if you don’t play.

Once we’re in, we’ll find that we can learn to cope with the occasional rejection, and we can even use it to improve how we date. But we can’t build the fulfilling, loving relationships we crave if we aren’t even in the dating pool.

I KNOW rejection feels scary and vulnerable.

But we can’t build meaningful relationships without risk: and that includes the risk of rejection.

Nothing important or meaningful in life was built without some risk. Just as in finance, high risk means high reward.

So get out there and jump in the pool! If you’re brave and take the leap, I think you’ll find that the water’s just fine.


PS. If you're drained from drowning in a sea of dreadful dating dossiers and want nothing more than to just find someone attractive and normal for once — I see you, I was you, and I'm here for you!

I walk you through how to spot the sneaky red flags that are lurking in your Hinge queue and how to gain the CONFIDENCE to walk away from them inside of my FREE workshop, Confident & Clear Dating. Confident & Clear is my FREE workshop where I walk you through how to avoid red flags and date with confidence — EVEN IF you hate dating and never want to use a dating app ever again. (I get it!)

If this sounds like your thing, get the free workshop here.


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