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kiss & tell : dating the ‘bad boy’

Welcome to our second installment of ‘Kiss & Tell’. At Lip, it’s important to us not to assume heteronormativity when talking about sex or relationships, but as our columnist is heterosexual herself, most of these columns will focus on issues related primarily to hetero dating. If you are interested in looking at relationships from a queer perspective, get in touch with Zoya at!

We’ve all been there. You’re out for a quiet drink on Thursday night when you see him across the bar: pork pie hat perched jauntily on the back of his head, low cut singlet showing off his muscular chest adorned with tattoos.  There’s a gold pinky ring on one hand.  He probably has a tongue piercing. As you approach the bar, he slides over and asks you what you’re drinking; nek minnit you’re making out in the car park while his friends cheer and wolf whistle from across the road.

Ok, so perhaps we haven’t all been in that particular situation, but I’d hazard a guess that most Lip readers (who are into men) have found themselves attracted to a bad boy at some point in their lives.  Bad boys come in all different shapes and sizes, but they are generally identifiable by two key characteristics: they have a winning, charismatic personality, and a devil-may-care attitude toward important things, like employment, their health, and your feelings.

My first experience with a bad boy was when I was the ripe young age of 19.  He was the lead singer of a band, and he lived up to all my smoking, drinking, drainpipe-jean-wearing dreams.  He only replied to my text messages if he’d started the conversation, and he barely acknowledged my presence in public.  But when it was just the two of us, we would spend entire nights sitting on park benches drinking red wine straight from the bottle and talking about art.  I read him my poems and he taught me how to play guitar.  We used to cook dinner together and in the summer, we slept outside in a hammock every night so we could look at the stars.  I fell madly in love.  He slept with my best friend and broke my heart.

Of course, after that I swore I’d never make the same mistake again – not only for my own emotional wellbeing, but also because I knew my friends would disown me if I put them through any more 3am crying-and-eating-the-entire-contents-of-the-fridge phone calls.  But after several subsequent years of trying to date good guys, and all of them somehow ending up being bad guys, I’ve found myself back where I started – in a car park making out with a dude in a pork pie hat (yes that was me).

Now, bad boys aren’t for everyone, but if you do feel like taking the plunge, there are a few things you need to remember.  Firstly, if he seems like a bad boy, he probably is.  He’s not the scarecrow with the heart of gold or the playboy who’s secretly looking for a real connection or whatever it is you’re imagining and/or hoping.  If you fall for him, he will probably break your heart.

That brings me to my second point: you can’t change a bad boy.  Every woman likes to think that she’s the person who is so special that she’ll make him want to change, and let me just say this – you are that special, but he won’t want to change.  Look at Katy Perry and Russell Brand.

Thirdly, and perhaps most importantly, there is a line.  A man who hits you is not a bad boy, he’s a criminal.  Playing games is one thing, but if he starts to alienate you from your friends and family, control your finances or even just make you feel small with insults and snide comments, that is emotional abuse and it is not acceptable.  No matter how good the sex is.

In the grand tradition of not taking my own advice, however, I started to think Pork Pie might have a heart of gold beneath his tattooed exterior.  I started to think I might be able to change him – he even trimmed his long pinky fingernail which he used for snorting cocaine because it creeped me out.  What a gentleman.

Then, when everything seemed to be going swimmingly, he stood me up.  I rang him to find out what was going on and he casually informed me that he was in the city – twenty minutes drive from where we were supposed to be meeting twenty minutes ago. I found myself feeling surprisingly hurt. Despite the fact that I already knew he was bad news, it didn’t make it feel any better when he behaved like it. If anything, it was worse, because I felt like it was partly my fault.  And his behaviour didn’t give me a thrill, and make me want him all the more. It just seemed so… unnecessary.

When he realised how annoyed I was he begged for another chance, and when I gave him one he did the same thing again.  So I called it quits.  Although I felt a bit sad (he was very hot), I congratulated myself for being so mature and sensible.  I went home, made a mug of hot chocolate with extra marshmallows, and snuggled up with my laptop to write this column. And lo and behold, I found that the original bad boy from my teenage years has added me on Facebook.  It can’t do any harm just to accept his friend request, right?

By Anonymous

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8 thoughts on “kiss & tell : dating the ‘bad boy’

  1. You’re out for a quiet drink on Thursday night when you see him across the bar: pork pie hat perched jauntily on the back of his head, low cut singlet showing off his muscular chest adorned with tattoos.</i<

    Horror of horrors, the bad boy is wearing his hat inside! This chap is clearly the devil incarnate. Ladies, have nothing to do with this maleficient entity!

  2. I wonder if there’s the equivalent ‘bad girl’ archetype? I can’t think of what the female equivalent would be, though I know there probably is one…

    • I think it’s pretty obvious that the reference to the hat in the author’s piece is part of her setting the scene. She wasn’t implying that the hat is a ‘bad boy’ characteristic. The cocaine fingernail, on the other hand, is more of a tell-tale sign…

  3. She wasn’t implying that the hat is a ‘bad boy’ characteristic.

    Well I certainly am! In the ‘wearing it inside’ context, anyway. I wear hats, I like hats, but I like the etiquette that goes with them too. Actually they would be pointless without etiquette: a man or woman who wears a hat while running away with your wallet is a bad sort, no matter how fine their hat is. Bad manners is indicative of bad character.

    • I think one reason why I distrust the wearing of hats inside is because it seems to be a partial mask, a way of hiding part of the face. (Like sunglasses). The effect is exacerbated inside because they have no practical reason for being on the head. Look, obviously there are far more important points of etiquette to get hung up on, this is just one that stands out for me.

  4. Hey i love a bit of adventure, but i am slowly learning that there are other ways to be spontaneous and have fun than with the ‘Bad Boy’ accompaniment. Hopefully my boyfriend is thinking the same ;)

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