How Do I Get Over My Fear of Success?

Estimated reading time: 12 minutes

Dear Dr. NerdLove,

I just got a quick question for you: How do I get over my fear of success with woman?

I (male 27 years old) used to be the stereotypical introverted nerd, you get it yadda yadda. I hit the gym, buried my tailor under my wardrobe for a custom fit, got out more and I started doing warm and cold approaches.

I got over my fear of failure pretty quickly actually. For all my fears, it turns out most woman are just flat out bored when being hit on/asked out on a date.

A few gave me a beaming smile (and sometimes compliments) while rejecting me, feeling quite obviously flattered. A rare few just told me to fuck off, so I did. But the vast majority of woman I approached more or less just shrugged and told me “not interested dude”.

So I said “okay”, and walked away.

Hell, I never knew handling rejection would be that easy.

I fully expected them to pepper spray me, or call their two meter tall bodybuilder boyfriend to beat me up, or pull out a knife to gut me with.

I asked a couple of my female friends that I was always attracted to out on a date. (separately and with time in between) they said “no”. I said “okay” and we were back to being friends, easily and without more than a minute of awkwardness.

Now comes the problem. Since I have improved, I started to notice woman, who do seem to be attracted to me. Such as staring me down at a party, while smiling 4 times in a row. Or that one other attractive female friend, that I made genuinely blush (and chuckle) with a joke that was actually meant to be comedic not flirting.

I know it’s ridiculous but if I notice that a woman actually might be attracted to me I get incredibly scared. For example: when I got hit on by a hot woman in a club, at first I froze, then I sprinted out of there as fast as my legs could carry me.

I don’t even know what exactly I am afraid off! There is no scenario or fantasy in my head.

And yet I am scared of hot woman liking me! The horror! It makes absolutely no sense at all!

The thing is, if I approach a woman, and I have no idea how my chances are, I can approach rather easily. After all why worry about it if I got no idea anyway.

Never tell me the odds. Indeed.

I feel like the DM of life just decided: “this guy, this guy right there? I am gonna roll on 1D10 table for phobias and slap him with the funniest one.”

So any tips on how to beat that fear? I mean I will beat it eventually, but some advice would be appreciated. On that note, thanks for your awesome site and advice, it helped me out a ton!

Best Regards

The Cowardly Lion

First off, CL, congratulations on all the positive changes you’ve made. You should be proud of what you’ve achieved so far, and I’m glad to see that they’ve been paying off for you.

Now let’s see if we can keep that winning streak going.

So, believe it or not, this is actually a common experience that people have. The fear of success is very real, and it ends up causing folks a lot of both anxiety but also headaches. After all, as you said: you’re afraid… of hot women being into you? That’s the most absurd thing in the world! This is what most people in your position dream of.

Well, the issue isn’t really that you’re afraid of hot women liking you or that you might actually start dating someone incredible. It’s not the success that you’re afraid of so much as what success might mean.

Here’s what’s going on: you’re used to being single and having little real luck with love. Failure and singledom are well known to you; you’ve functionally mapped every corner of it and you know it like the back of your hand. It isn’t pleasant, but it’s an area you know well. Success, in this case, is very much the unknown country for you. If you were to approach someone and they were into you as much as you were into them and then you ended up with their number or plans for a date, then you’d be venturing into the unknown – without any sense of where you’re going, what you’re doing and without the supports and guide rails that you’ve developed over time.

To be sure, it seems weird when you write it out or say it out loud but success would mean getting forced out of your comfort zone and having to take risks that you’ve never experienced before. The known isn’t what you want, but the familiarity of it brings a certain sense of safety. At the very least, you know what to expect and how to handle it. In this new world, where you have a date – a date that might even turn into a relationship? Well, suddenly shit has gotten very real.

But why would success be scary? Isn’t this what you’ve been working towards, dreaming of, imagining all this time? Well, yeah, of course. But it’s what you’ve been imagining. What you imagine is entirely under your control. The dates and relationships you can imagine after achieving your goals all play out in your head the exact way you want them to. Even if you don’t picture it all going perfectly smoothly or you allow for conflicts or mistakes, it’s still unfolding according to the script you are writing. You, quite literally, can’t fail.

Reality doesn’t work that way. Success in reality means that now you’re responsible for every choice you make, without the comfort of knowing your choices are inherently correct and will result in the outcomes you want. Before, the stakes were manageable. If you failed, nothing materially changes. Yeah, you may feel down for a bit, but you know that territory well. Now, you feel like you’re walking a tightrope that seems to have no end in sight and it feels like if you put so much as a toe wrong, you’re going to fall into the pit. Failure before meant a perverse form of safety. Now you’re in a place where the thing that you’ve wanted is within your grasp and you can fuck it all up and lose everything.

This is why hope can be a motherfucker; there’re few things more devastating than when you have hope and it gets snatched away. But, as the man said: the reason why we fall is to learn how to get back up again. And hope is part of how we muster the will and the courage to get back to our feet.

Of course, just understanding this intellectually doesn’t change how things feel. I know that planes are actually much safer means of travel and that plane crashes are rare and turbulence doesn’t bring planes down. That doesn’t stop me from trying to hold the plane up through sheer willpower when my flight hits a bumpy patch. So it is with the fear of success and what success would mean – you may recognize it for what it is, but that doesn’t stop you from feeling it.

But while you may not be able to stop yourself from feeling that fear, knowing that you’re feeling it and knowing what it is allows you to change your behavior. As the litany goes:

“Fear is the little death. Fear is the mind-killer that brings total obliteration.

I will face my fear. I will permit it to pass over me and through me.

And when it has gone past, I will turn the inner eye to see its path. Where the fear has gone there will be nothing. Only I will remain.”

Or to put it another way: “be afraid and do it anyway”.

Rather than letting your fear drive you away when you face success, take a deep breath, let yourself feel what you’re feeling and then just keep going. Even if your voice is a little shaky, even if you’re trembling a bit, just breathe and keep at it. The women you are into will understand nerves, they’ll likely even be a bit flattered that you’re nervous. But this is just the fear of the unknown and the risks that come with it. The more you face the fear and push through it, the less you’ll experience it, because the unknown will increasingly be just the known. One of the formulas for confidence is fear + survival. Because you’ll have gone through it and come through the other side, you’ll have a much better understanding of what you’re doing, what you’re in for and what to expect.

While there’s always going to be elements of risk and the unknown in any relationship, what feels like a tightrope soon becomes a 2×4, which soon becomes a bridge – still potentially precarious, but far steadier, more stable and less risky.

Getting used to feeling fear but not letting it stop you will serve you well in other parts of your life – both dating related and otherwise – when you’re having to take risks and facing potentially unknown consequences. Fear is just your brain trying to keep you safe; that doesn’t mean that it’s right. Recognize it, acknowledge it, and keep going, and you’ll come out the other side. And when you look back to see, there’ll be nothing. Only you will remain.

Good luck.

Dear Dr. NerdLove:

I have been hanging out with this girl 7 times now with her doing the majority of the asking not me. She has canceled meet ups before quite a bit so it could have be more than 7 times if other hangs weren’t canceled. She had also brought up future plans to hang out quite often also.

On these hangouts there has been no flirting or physical touch or signs to make a move on her. Basically no initiation from either of us. This girl is 37 and I’m 45.

What do I do with this girl?

Going Nowhere Fast

Alright so I have to say this right off the bat: you really don’t want to refer to a grown-ass adult woman as “girl”. She’s 37, not 16, she’s a woman, not a girl. While I’m sure that’s not your intent, calling her “girl” is patronizing at best and a little insulting at worst. Do yourself a favor and start working on breaking that habit; trust me, it’ll spare you a lot of unnecessary grief in the future from folks who aren’t going to be generous about your intent here.

Now with that out of the way: I think the bigger question here is “what do you want out of this relationship?” There’re two people involved here, and neither of you have made a move to take things in a more physical or romantic direction. Since you’re the person writing in, you’re the only one who can really answer the question of “what’s going on in your head over this?”

I think we can say with a degree of certainty that she likes spending time with you. After all, you’ve hung out multiple times – 7 at least, and more planned in the future. She’s been initiating a lot of the plans you’ve had, so clearly she’s either getting or hoping to get something out of this. Maybe she’s digging you as a platonic friend, or maybe she’s been waiting for you to give her the sign that you’d like to take things up a notch. You don’t say whether you are interested in seeing her as much as she seems to be in seeing you; are you not making plans because she tends to bring them up first? Or are you just going with the flow and waiting to see?

So the first step is simple: are you happy with how things are going? Are you hoping that this is going to lead to some kind of relationship beyond the platonic? If the answer to the first question is that you want more, then the second question becomes: why haven’t you made a move to escalate things?

This isn’t an idle question. It’s one that really deserves some consideration. If it’s a case that you’re kind of “meh” about her as a potential romantic or sexual partner, but not as a friend, then continuing on will likely continue the status quo. Because you’re not giving her more signs that you like her as more than a friend, the odds that she will be the one to escalate are relatively low. If anything, the odds that she may get frustrated (if she’s looking for more than friendship) and break things off grow the more times you see each other without anything happening.

If you’re just not feeling it in general, either as a potential partner or as a friend, then all you’re doing is wasting her time – time that she could be spending either finding someone who is interested in her or time with that person. I’d strongly recommend just saying “hey, I’m not feeling it, best of luck to you” and ending things quickly and as cleanly as possible. It’s going to be messy – this has been weeks of her time and an investment of energy into you after all – but it’s still kinder to just do it in one quick move. The clean break heals the fastest after all.

If you’re interested in her as more than friends, then someone’s going to have to make a move to escalate the situation and that may as well be you. As I’ve said before: women get just as nervous, wondering if their dates and crushes like them as much as they like their dates and crushes, and are just as afraid of getting rejected as men are. By the same token, men are socially rewarded for being more aggressive in progressing a courtship in the early stages, while women are frequently punished, socially, for doing so, so your being the one to make the first move to level things up poses less risk. So if you’re interested in more with her, then the best thing you can do is to start acting like a potential lover instead of a friend.

Now, there’s a potential third thing happening here that would affect how you might want to progress things: she’s interested in you, but she may demisexual or asexual. That is: she may not necessarily feel overt sexual desire until she feels more connected to you emotionally or she may not feel much sexual desire at all. 

This is why I would recommend saying something rather than just going for a kiss. Adding some flirting into the mix when you hang out the next time is a good start and a way of signaling that you like her as more than a platonic friend. If she responds positively, then I would recommend picking a particularly romantic or charged moment, look her in the eye and say “I’ve been unsure about how to do this, but I really want to kiss you right now.” Then give her a moment to either give you the green light or wave you off. If she gives you a positive response, cup her cheek very lightly and lean in to kiss her. If she gives you the wave-off, then take it with good grace. Don’t immediately assume that this means that she’s not interested; she might be surprised, might need a minute to process things or may need to decide if she’s ok with being kissed. Give her the room she needs and let her tell you how she feels. Don’t try to kiss her again until she gives you the green light.  

If she’s not interested in you romantically or sexually… well, now you have to decide if there’s enough there that you would like to be friends with her. If the answer is no, then again, I recommend breaking it off as quickly and cleanly as possible. If yes… well, carry on as you two have been. No need to change something that’s been working so far.

But as I’m always saying: if you want things to be different, you have to do things differently. Someone’s going to have to take decisive action to break the status quo and since you’re the one writing in, you’re the one who’s functionally stepped up to the plate. Time to make your move, one way or another.

Good luck.