Ask Dr. Nerdlove by Harris O'Malley

How Do I Stop Feeling Like A Dating Failure?

DEAR DR. NERDLOVE: I’m starting to believe I’m not actually capable of dating someone and I’m becoming afraid of dying alone.

I was bullied most of my school life, I probably didn’t help myself much at the time but now I realise the experience left me socially isolated/awkward, lacking in confidence and self-belief and believing I had little to offer in life. I’m now 24 and all in all I really cannot complain: I have my health, I’m financially stable and I have the career I always aspired to which offers a fantastic work/life balance. I’ve always been somewhat introverted but I have my friends I see (as and when work schedules allow) I do socialise more now and have become a bit more self-aware and hopefully less awkward. I’m certainly no party animal and I choose not to drink. I prefer to spend my time away from work with outdoor adventure activities, exploring different countries, keeping fit, generally seeking to learn and develop in and out of work and charity/volunteer work.

However, my dating/love life has not had the same success, in fact much the polar opposite. I think this stems from a bad dose of what you’d probably call oneitis I had in school: in hindsight we were opposing ends of the social spectrum so it was an impossibility really. She was perfectly polite and respectful in her rejection but unfortunately once word got around it all fed more ammunition to my childhood tormentors and as is the way in school the majority sided with the socially dominant bullies. This has left me with crippling approach anxiety for fear not so much of the polite ‘No, thank you’ but more the nuclear explosion of abuse and psychological torture that historically followed. So I’ve hit 25 and not managed a meaningful romantic relationship. Not one.

Of the odd, irregular night out I enjoy bars and pubs but clubs are really not my scene. I suppose this limits the number of women I meet but I also think it’s probably better to meet them doing what I enjoy. I have many female colleagues as well (I realise work isn’t necessarily the best or even appropriate time to approach anyone).

My trouble is, if I meet a girl who I find attractive (personality, physically etc) the fear starts brewing. I automatically assume they’re already spoken for, wouldn’t be interested or could do better and I get tongue tied: either I end up saying something stupid or blanking them. Even worse, sometimes I manage a pleasant but platonic conversation when it’s just one-on-one, but cross paths with her with other people present, I panic and blank them. Probably as creepy as it is offensive and I don’t mean to be that way.

I have friends and colleagues who really have made a great effort to help. I regularly hear: “You’re not exactly ugly, impressive physique, you have a great career which involves helping people and you really can say you’ve saved more than one life, you’re passionate about your job and hobbies, well-travelled ambitious, intelligent, honest, well-meaning, pretty funny when you want to be AND you can cook! That’s quite the package to offer”

I go away feeling better about things but as soon as I’m faced with the pretty girl it all crashes back: Nope. I’ve got nothing to offer her. She’s out my league.

I’d love to follow the advice of just ask, nothing to lose, ask straight away before you’ve become over invested in the answer but, being a bit socially awkward, it takes a while for me to become comfortable talking with someone and by then I have overthought everything and convinced myself not to bother. On the incredibly rare occasion I’m seriously thinking of asking I don’t know how to, I can’t work out how to make the conversation more than just platonic chat or professional courtesy. On the even rarer occasion I’ve actually asked (unimpressively, timidly and stammering) it’s always a no. A polite and thoughtfully worded no (mostly) but still a no.

I’ve managed a few (we’re talking less than 5) dates in recent years. None successful. To be honest, none of them have even been enjoyable. She may be very beautiful with a great personality and I may have wanted to see her again but the pressure I seem to put on myself believing that I have to try and act like someone else because they clearly won’t like me just leaves me feeling deflated, defeated and exhausted. They never want to meet a second time. The reality is, I don’t enjoy the process of meeting someone or getting to know them (mainly due to my lack of self belief) but I don’t want to grow up and die alone. Unfortunately, in my work I see this happen scarily regularly and with every partially decomposed body that was only found cos the neighbour hasn’t seen them for a while it hits me every time that I’m possibly seeing my own future.

The internet is full of warped and contradictory “…treat em mean keep em keen…” advice filled with “infallible techniques and pick up mind tricks” and I’m buried under a belief that you need to be a psychological genius to work it out.

I guess my question is what do I do? Where do I start?

Feeling Like Failure

DEAR FEELING LIKE FAILURE: You have a classic issue, FLF, one that a lot of men have: you’re too busy fighting ghosts of the past to live in your present.

I see this a lot in my line of work. Hell, I’ve been through it myself. And it almost always happens the same way: there was some event in high-school – it’s always high-school – that’s convinced you that you’re an unf

kable homunculus, that you’ll never actually be good enough  to be worth someone’s interest and if people realized that you were interested in them, they’d run screaming like all of Hell and half of Hoboken were after them.

And honestly? It’s all bulls

t. It’s all bulls

t and it’s born from bulls


Notice how I said that this always seems to revolve around an incident in high-school? That’s because high-school is when people are at their casually cruellest, for no good goddamn reason. Not out of malice – necessarily, most of the time – or out of a desire to destroy something, but because of the one big secret of high-school: nobody knows what the f

k they’re doing and everyone is terrified by this. High-school is the nadir of most people’s lives. Our bodies are in constant flux as our hormones are surging out of control. We’re dealing with desires and impulses that we don’t know how to handle, but we know they’re so much bigger than we imagined. We’re in this bizarre liminal state where we’re convinced we’re adults, and legally we often are. But we don’t have the knowledge or experience that comes with adulthood, and the actual adults around us alternate between expecting us to be grown up and treating us like children. Meanwhile we have no goddamn clue who we are or what we’re supposed to do and so we grab for anything we can that will serve as an identity or purpose. We strive for status and power because we’re terrified of not having it. And the people who do seem to have it often wield it like a club. Sometimes it’s because they think it’s what they’re supposed to do. Other times they lash out to cover up their own fear and insecurities, keeping everyone from questioning their position by drawing their attention to someone more vulnerable.

And if you’re not one of the people who’s at the top of the heap – or you’re so perpendicular to the social ladder that you don’t come in contact with it – then odds are you’re one of the people who gets s

t on. It’s always easier to throw attention at someone who’s weaker and less influential than you, especially when they don’t fit artificially determined standards or niches.

(Doubly so if you have some behavior that’s seen as “not normal”… which just happens to be defined as non-normative sexual orientations, non-conforming gender presentation, neuroatypicality and racial differences.)

So yeah if you’re not someone who peaked by 18, then high-school probably sucked and you probably went through some s


But as significant and momentous as it felt – and again, I’ve been there, done that, got the therapy bills to show for it – it’s all bulls

t. Somebody weaponized their own insecurities and shoved it into you. Problem is that instead of rejecting, it you’ve let it infect you and metastasize until it’s taken over your system like an emotional cancer.

And look, I get it. I’ve wrestled with this s

t myself. My high-school experience blew goats, and the only reason why things weren’t worse for me was because I was lucky enough to grow up before mainstream adoption of the Internet, before Columbine, before social media… before so many things really. It took me a long goddamn time to get over it, because I internalized all that s

t too. I made all of the s

t I went through part of my identity.

But I didn’t have to. And neither do you.

So much of what you’re dealing with are the after effects of this bulls

t. When you’re approaching people, you’re remembering everything about the woman you had a crush on. You’re remembering that “EWWWWW HOW DARE YOU EVEN THINK IT?” moment from the folks who felt like they had to enforce their weird and arbitrary social borders. You’re still more than half-convinced that they were right, that you’re too awkward, too weird, too creepy to ever insult them by expressing interest.

You’re not. You’re just hearing ghosts. And you can shut them up.

And here’s the thing: you already have the skills you need. You don’t need those bulls

t “seduction secrets” people are peddling. You’ve got friends, co-workers who think you’re great, and a whole host of experiences and stories under your belt. Those are all you ultimately need to meet people, find dates and start relationships. If you can make friends, you can get dates; the skills are fundamentally the same. The only difference is how you direct them.

What you need, more than anything else, you need to learn to love yourself. Not think “you ok”, not “get comfortable with rejection”, but learn to love yourself. Not the self you are when you’re in a relationship or the self you think you need to be for people to like you. You need to be able to love yourself, right now, as you are. Maybe it’ll take talking to a therapist. Maybe it’ll take making lists of your great points and reading them regularly so you remember they’re there. Maybe, as stupid as it may sound, it’ll mean standing in front of a mirror and complimenting yourself and giving yourself regular affirmations.

It doesn’t matter how you get there, so long as you do.

You need to be able to recognize your awesome as YOUR awesome, not by how valuable other people find it. Because the more you can learn to love yourself and see the value inherent in you just being you, the less you feel like people are “too good” for you. You don’t feel like you have something to prove – not to your friends, not to the random strangers that you are attracted to, and certainly not to the ghosts of your past.

This is important because it means that you will stop being so afraid of other people. Not just the possibility that they’ll reject you, but the fear that they see something in you and have found you unworthy. Because that? Is alllll kindsa bulls


The more you are able to recognize your worth, really believe in it, the less you’ll feel like you need to pretend to be some version of you that measures up to expectations you seem to think other people have.

And, straight talk my dude. High-school was seven years ago now; that’s damn near twice the length that you were actually there. It’s time to quit letting bulls

t from f

ked up teenagers – because we’re ALL f

ked up at that age – live rent-free in your head. You’re better than that and you deserve better than that.

You’ve got this.

All will be well.

Please send your questions to Dr. NerdLove at his website (; or to his email,