I am a grown-ass woman. I own my own business, keep it tight for 40, and I've never been married. I don't mind the not being married part, but what I am sick of is that I keep dating the same type of guy — the bad boy. It's like I can't help myself. I tried to go out with some insurance dude the other day, and I was practically asleep before the meal got to the table. Give me a guy who rides a Harley, or likes to jump out of a plane, and I'm there. The problem is, after a while, it seems like the bad fades away, and all I'm left with is the boy. He leaves dirty clothes everywhere, "forgets" about the shower he promised he'd come to with me, and eventually ends up screwing some younger chick. But when I try to go out with a "straight-laced" guy, I end up jumping on the first bad boy I see. Help! I'm attracted to what I'm attracted to, but I want to break this cycle. Are there any bad boys who aren't a glorified manchild?
Sincerely, Wanting A Change
Oh, I know the type you speak of. The ones with the irresistible glint in their eyes, so all they have to do to light your fire is look at you. One grin and you're gone. But eventually, if I can stretch the metaphor just a wee bit further, you end up with a chapped ass. And nobody wants that.
My sense, from what you write, is that you keep it wound so tight during the day, you can't unwind without a little help. Or maybe a lot of help. That's where the bad boy comes in. The problem, dear Wanting, is that it's not him. It really is you. Eventually, his tricks wear thin. You're just not as excited by him as you used to be. He may leave first, but really, you started checking out a while ago. To feel the excitement you crave, you need more than he, or in the long run anyone, can possibly give. You, dear Wanting, need to be your own badass.
Before you call bullshit, consider what cleaving to the victim role means. You really can't do anything. And even if you feel you've been jilted, it doesn't matter. You know what to do.
You like Harleys? Get one! You want to jump out of a plane? Do it! What kind of adventure do you really want? And note, sex is a terrible answer. The best sex is more of an exploration, really, but aside from that, you can get it anywhere. This is especially true if you're willing to travel solo to a foreign country to find some cliffs to hang-glide off of. So just assume you'll be able to take care of that. (And pack condoms!)
Here's what you don't want. You don't want to wake up, 10 years from now, wondering whose life you've been leading. So long as you're looking for someone else to unlock your inner beast, you're not really answering the call of your own personal badass. Or, as put by the late great filmmaker Billy Wilder, "Trust your own instinct. Your mistakes might as well be your own, instead of someone else’s."
I am attracted to my boss. It's the old cliché, he's married. But he flirts back. And I can tell from what he says that he's not too happily married. Nothing has happened yet, but I want it to. My job is practically disposable, but his isn't. So he'll never make a move. But every time I try, I can't seem to figure out how to make a move. It's not like when you're out and meet someone at a bar, and things just happen. How can I tell him about my feelings?
Love, Working Girl
Dear Working Girl,
You know the answer, it's why you haven't done anything. "Things" at a bar don't just happen, you're still there. You know how to take it to the next level when the signals are right.
But you didn't ask if it was smart, only how. So.
Assuming you're reading the situation correctly, and your job really is expendable, quit. Well, find a new job first. Then quit. It sounds like this boss isn't your direct supervisor, so it would be weird to reach out to ask for a reference, but that's a way to be in touch with him after you're gone. Even if you have that awesome new job. For one, your interest may evaporate. If that's the case, you've really saved yourself. But if you're still pining for the boss, who knows what might happen. Don't be surprised if he refers you to your actual supervisor. Even if you meet and hit it off, chances are good you'll end up bruised. That's the game for us all, though, so there's no avoiding at least some heartache.
Most importantly, let this be the impetus to do the one thing that will matter most in the long run — get out of that dead-end job. Love yourself enough to have a job you don't consider "disposable." Nothing about a life really is.
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