Love the column, listen to the podcast more than is probably normal. And now I have a question. It's pretty random and doesn't apply to many people, but I thought I'd get your take anyway.

I'm 26 year old straight female. In 2006, I took some sex pictures with an ex-boyfriend (I know, I know) and now they're back to haunt me. Someone—I'm sure it's the ex but can't prove it—has been posting them anonymously on various forum websites and linking them back to my Facebook page. I'm getting some emails from creepers asking for more pics, and a bunch of friend requests from people who have seen my lady bits. Now it's escalated to extortion, and he's threatening to send the pictures to my friends, family and coworkers. I've had to tell my mom and my male boss to protect myself in case this guy gets really crazy, and I spoke to the police this weekend. I'm doing what I can to make sure this doesn't get out of hand and ruin my life/traumatize my mom.

My question is this: I have a fairly new boyfriend (dating since January) and I'm wondering if it's too early to bring him in on this. I'd rather he find out from me than someone else (or a creepy anonymous email), but I'm also nervous about what he'll think. Any advice?

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My response after the jump...

It sounds like you're doing everything right, NIC.

Some folks are no doubt snorting to themselves after reading that. "If she had done everything right," they're muttering, "she wouldn't have trusted that asshole with those pictures."

Yeah, yeah: NIC certainly knows now—we all know now—that she picked the wrong boyfriend to trust with sex pics. But every relationship requires a leap of faith. Someone who won't take a chance, someone unwilling to risk a little heartache/headache, will never find love or sexual fulfillment. Let's give NIC the benefit of the doubt and assume that her ex-boyfriend, if he is the culprit, didn't come off as a crazy and vengeful piece of shit when they met. Like most people with asshole exes—think back on some your own, folks—NIC took a chance on this guy because he seemed like a decent person. NIC was mistaken about this guy. But her willingness to take a chance on him wasn't a mistake. She needs to learn from this experience, she needs to hone her bullshit detectors, she needs to keep her eyes open for the POS warning signs in the future, but it would be an even bigger mistake if she stopped trusting or taking those leaps of faith. Or those pics.

Back to you, NIC: warning your mother, warning your boss—that's the the right thing to do. Your mother should delete any strange emails she receives and avert her eyes from pictures she may not want burned into her brain; your boss should do the same, NIC, and if he isn't a POS himself he will have already offered you his support and sympathy. You are, after all, the victim here. As for your boyfriend...

You should tell him what's going on.

Backing way the hell up: I wouldn't give you the same advice if you had only been seeing this guy for a few weeks. While everyone knows that life involves a certain amount of drama (some of it ex-generated), and that being in a committed relationship means supporting a boyfriend/girlfriend through a drama, very few people are anxious to get involved with someone whose life is nothing but drama. Being pulled into a drama in the early stages of a relationship frequently scares off new boyfriends/girlfriends because they rightly worry this drama is just the first of many. Additionally, most people are looking for partners with sound judgement. Since everyone is or should be aware that too much drama too soon can kill a new relationship, dumping a drama on a new boyfriend/girlfriend demonstrates bad judgement. That can result in your getting dumped. Also, many people regard being pulled into a drama early on as emotionally manipulative. It can make a new boyfriend/girlfriend feel obligated to come through with a level of emotional support that a new partner has yet to earn; it can also leave a new boyfriend/girlfriend feeling obligated to make a commitment they're not ready for, i.e. a commitment to provide support until the drama ends.

Please note: all of the above only applies to minor-to-middling dramas, those manageable life crises that a person can shield a new boyfriend/girlfriend from. Your mother is dying of cancer and you're an emotional wreck about it, prone to crying jags and meltdowns? You'll have to let your new boyfriend/girlfriend in on that, let him/her decide if he/she wants to keep seeing you regardless, and not be surprised if he/she bails.

Sorry—that took some time to unpack. Back to you, NIC: six months isn't too soon to bring a new boyfriend in on a drama, to expect and receive a little emotional support, particularly if you think there's a chance this stalker/ex/POS could track your current boyfriend down. Better he learn about the pictures and the POS ex from you, NIC, than learn about them from an anonymous, malicious email. If you're worried that your current boyfriend will react badly—if you're worried he wouldn't want to date a girl who would take pictures like that—better to discover that now, NIC, and dump this new POS, then to have those pics and your history hanging over your head for the rest of your life.