You know what they say (where by ‘they’, I suppose I really mean ‘good guys’): girls want bad boys. Why this is, I don’t really know. Maybe it’s that it’s dangerous, and danger is exciting. Maybe it’s because they think their parents will hate him. Maybe they want to reform him with love. Maybe they think bad boys get into a lot of fights, and scars are sexy. Whatever the reason, girls in fiction always seem to go for the bad boy – and it’s hardly limited to fiction. Consider how many love letters and conjugal visits convicted serial killers get, and I’m not even joking when I refer to this phenomenon. It’s called hybristophilia. And that’s not even touching on Stockholm syndrome.
In all seriousness, one of the reasons put forward to explain this phenomenon (in the “jerk jock” kind of way, rather than the hybristophilia kind of way) is very simple: the “bad boy” is much more likely to be more forward and assertive about their pursuit of women, and less concerned with adultery and one-night stands, so they can get more women by default. Furthermore, let’s face it – they’re more likely to lie about how many women they’ve been with, and what they’ve done with whom, aren’t they?
Pirates, when they’re in port – which isn’t often, remember – tend to get a lot of women. Well, who can blame them? They’ve been on the seas for months at a time, and the cabin boy’s getting old. Not to mention, they probably have quite a stash of booty built up, meaning at one end of the scale we have plenty to pay the hookers, and at the other end, plenty of pretty things to pass on to the local ladies as a tool in the games of seduction and romance. And the women? Well, some of them are being paid, as I’ve said, and some are probably interested, because let’s face it – pirates are bad. How bad? At the least, we’re in Anti-Hero territory (and they always get more girls than the hero.)
Don’t kid yourself – pirates are bad. There’s levels of bad, certainly, but it’s fair to say that they steal, they probably kill, and odds are they aren’t too fussed on certain other matters of legality and morality. If you know they’re a pirate, they probably also flaunt their badness quite openly, at least in your circles. At best, we have an anti-hero – a Jack Sparrow type, to take the Pirates of the Carribean example. He lies, cheats, steals and is openly flamboyant about the fact that he is neither a nice or good person. When it comes to the ladies, he doesn’t hide behind pleasantries. He cuts right to the chase, but he’s oddly charming about it, and he does have a line somewhere (even if he toes it frequently enough that it’s noticably scuffed). He’d certainly never take a lesson from the opposite end of the scale, the really bad pirate, and just remove a girl of her clothes and have his way with her – and yes, there are pirates who would do just that. After all, there’s enough on them that they’d be hanged anyway, and they’ll be out of the way of the local authority in days. There’s a certain recklessness about authority that can develop, here.
Anyway, back to my point: the benefit to a pirate (at least, one of the ones closer to the anti-hero end of the scale) if you’re cruising for a bad boy is that they’ll be gone before too long, and odds are good that you’ll never see them again. This isn’t so good if you want to redeem him with your love, but if you’re feeling a bit reckless and want some danger in your life, or to flirt with the boy you’d never take home to dear old Mum, a man who’ll be gone in a few days to never be seen again certainly isn’t a bad choice. At least you won’t have to worry about getting caught up in his illicit activities.
How does this work in actual roleplay? Well, if you’re looking to strike up some romance with a pirate, it will probably be – ahem – a brief, intense and passionate but respectful relationship. Wait, who am I kidding? He’s a pirate – kick respect off that list, like as not. Not a lot of people are really keen to roleplay this kind of business, and I certainly don’t fault them for that. But if you’re playing a pirate, keep this in mind: your history is probably peppered with sexual liaisons, probably a few at this very port. If you’re not trying to pick up now, you may well be keeping half an eye open for that woman you were with last time, if only to stay out of her way so she doesn’t notice it’s you – or heck, maybe you remember her from last time and want to see if she’s free tonight!
If she’s not, though, it’s alright. You’re bound to find someone – you know what they say. Girls want bad boys.