My Old Boss Sent Me a Douche and I Don't Know How I Feel About It

My Old Boss Sent Me a Douche and I Don't Know How I Feel About It
Illustration by Jim Cooke/GMG. :

Welcome to Dear Jane, Jezebel’s advice column.

Dear Jane,
Last week, I found out that my former supervisor from a job I left in August, an older man who I trusted and considered to be a mentor and friend, is behind a series of anonymous “prank” packages I’ve been receiving. The first, sent to my house on my birthday from a local post office, contained an adult toy and all the necessary accessories to use such an object. When I first received it, I figured it must be a prank from one of my close girlfriends and was a good sport about it. After a few weeks, no one had confessed and it suddenly became less funny and more creepy. The second package was sent to my office before Christmas, nearly an hour away, from a US post office near my workplace, contained hygiene products (including a large bottle of Summers Eve feminine wash), and a note proclaiming that it was sent from my new coworkers as a Secret Santa gift. This crossed the line, I’m a professional and I take my new job very seriously. Obviously, I don’t need to be receiving embarrassing anonymous packages to the office and now it was apparent that someone knew very well where I lived and worked and had traveled there to mail the packages priority overnight. I actually called this guy the night I received it to see if he knew of anyone at my former office that could be behind this, and he pretended not to know anything. Eventually he called me to confess in a fit of guilt, saying that it had been bothering him since I called and his wife finally got him to confess to sending me “practical joke packages” (for the record, I don’t know if he told her what was in them), and she told him that he had to call me because I was probably freaking out, which I was.
My question is, what the hell do I do now? Obviously I have no desire to continue what I thought was a valuable mentorship with someone influential in my industry. I know that this is not my fault in any way, and I’ve always maintained appropriate boundaries. The last few months at the previous job were stressful for both of us because of organizational changes that led to his leaving as well, so it’s possible that he got the nature of our relationship twisted during that time period and after when I no longer worked for him. Do I have any obligations as a feminist to take steps to prevent him from doing this to the next woman who reports to him? Can I afford to take him at his word that he meant it all to be a joke and had no idea I would take it this way and wouldn’t do it again? What on earth is wrong with men like this?
Thanks Jane,
Please Don’t Mail Me Vibrators

CALL THE POLICE! For fuck’s sake, call the police. This isn’t a misunderstanding about the nature of your relationship. It also has nothing to do with feminism. This man is obsessed with you and he’s a crazy person and before you go worrying about what he’ll do to the next person, you need to protect yourself. You think a man who drives to another zip code to mail a former subordinate a douche has one conversation with his wife about it and suddenly he’s fine? (I’m not even sure I believe that part; why would you?)

I’m a little worried about you, too. The work you’ve done here to apologize for his behavior, blame yourself for it, AND make doing something about it solely about protecting other people is, for lack of a better phrase, kind of bananas. You are in danger, period. This is not normal or okay, period. Call the police and then a good therapist.

Dear Jane,
I have been asked to be the best man for a buddy’s wedding. We are both professionals in our late twenties, currently living in cities three hours apart. We grew up in the same small village in a rural area and have been friends since childhood.
One wedding tradition from our rural community is the “Stag (or buck) and Doe, a kind of pre wedding drunk-fest hosted by the members of the wedding party, the sole purpose of which is to raise as much money as possible for the engaged couple. Raffle tickets for donated items are sold, and people are encouraged to play various games of chance which can set one back a substantial amount of money over the course of the evening.
My buddy sent me (and the rest of the wedding party) an email this week saying that he and his bride have chosen not to have a Stag and Doe. I was greatly relieved, because I have always felt that this is a crass money-grab. However, he went on to say that they WILL have a raffle of “donated” items. He expects the members of the wedding party to collect “quality” donations in kind, and then to sell the raffle tickets at work and to friends and family. Crass money-grab without having to look the poor saps in the eye! It would be career suicide for me to sell such tickets at work to my colleagues who do not know the groom and I will not do it. I do not relish asking people to donate items or buy tickets.
The other groomsmen feel the same way that I do. Our buddy has a good job. He and his fiancé own a home. The rest of us are saving towards down payments.
So, my question is, how do I respond to this email truthfully without ruining our friendship?
Grumpy Groomsman

Oh, wow. Why are you friends with this dude? If it’s because you have deep, heartfelt conversations and you understand each other and support one another throughout life’s ups and downs, then surely you can talk to him about this. If it’s more out of inertia, then maybe you do nothing. Just tell him you couldn’t find any takers. Who cares? Not you, right?

If it’s the former, just know that weddings make everyone crazy and your sense-talking might not be received very well right now. You and the other groomsmen are 100 percent right that this is inappropriate and gross, no doubt. Maybe a simple note signed by all of you that says, “Hey guy, we’re all really excited to be part of your special day. We’re also super UN-excited to be hawking products around our offices in order to pay for your honeymoon, or whatever. Please don’t make us do this! It’s embarrassing. Can we help you brainstorm another way to raise some cash?” And then add the link to one of those honeymoon fund websites (also gross, IMO). That’ll get you out of the begging-for-cash situation at the very least. At most you won’t have to be friends any more! Huzzah.

Dear Jane,
I have a problem. I’m too nice.
I can’t say no to people, even people I dislike. I get asked a lot of favors, because I rarely turn anyone down, even if it’s a favor for someone I don’t particularly like. I always agree, always say it’s fine because to turn them down would be mean, because I’m too worried about hurting their feelings to turn them down, even if it means sucking it up and making myself miserable. I apologize for everything, constantly- for talking too much, for saying the wrong thing, for every little thing under the sun. I’m so tired of it!
Here’s a recent example: For some time, I’ve felt the need to end a friendship. I used to consider Carrie a close friend, and came out to her as gay very early on in our friendship. She’d agreed not to tell anyone, and then promptly outed my sexuality to all of our mutual coworkers. A life lesson on who to trust, right?
It wasn’t until five years later that someone told me that Carrie had spilled the beans so long ago. I confronted her about this, and she apologized. It seemed genuine, but I no longer felt as though I could trust her, for obvious reasons. After some time, though, I told her I forgave her. We no longer work together, so I no longer encounter her regularly, which made it easier to offer my forgiveness and be done with it, especially since we have mutual friends. Everything would be easier, I thought, even if I wasn’t sure if I really forgave her or not.
Then she asked if we could still be friends. Wanting the awfulness to just be over, I told her we could be. But since then, she asks to hang out from time to time (though not nearly as often as before), and I’m constantly coming up with reasons to cancel, even if I have no desire to see her. But she seems determined to keep trying, even as I hope she’ll get the message. The distance has made me much more aware of other qualities she possesses that I do not admire. Things that, even aside from her betrayal of my trust, make me not want her in my life anymore. Our views and values really don’t align.
I realize that I need to be honest with her about how I feel, in a way that I haven’t been up until now. Attempting to let our friendship fade away isn’t working, and she deserves my honesty. And damn it all, I’m still, to my intense frustration, worried about hurting her feelings!
How should I stop being so untruthfully nice to her, and in other situations? To do so feels dishonest when I don’t mean it. How can I overcome something that I know has been socialized into me for the entirety of my life? Women are supposed to be “nice,” but I’m sick of it. How can I learn to be more assertive and stand up for myself? Having empathy is a good thing, but there comes a time when enough is enough. There’s a difference between being a kind, thoughtful person and folding like wet cardboard.
Rather Be (Not So) Nice

You don’t sound that nice to me, and I mean that as a compliment! Since when is it nice to tell people what they want to hear? You’ve basically straight-up lied to this lady and now here she is thinking she doesn’t suck as hard as she obviously does. That is rude. Especially to the rest of us who now have to work twice as hard convince her that she’s kind of an asshole. When you can muster the courage, if you still care at that point, let her know she violated your personhood in a really significant way and you don’t trust her. If she wants so badly to be around you, she’s got a lot of work to do on her end. Then let her sit there and figure it out while you go find real friends.

You’re right that women are conditioned to be accommodating to assholes, that is true and a giant problem. But here’s the thing about assholes: they LOVE being assholes. Being assholes is their favorite. They love it so much they don’t even think it’s a problem, so telling them or not telling them usually garners the same result. It’s awesome that you are over worrying about everyone else’s feelings above your own and ready to move on to another way of being. Start small. Next time a server asks you if your meal is okay when it is not okay, say something. “The conversation is great, but this burger is not.” They might be bummed or they might bring you ice cream! Either way, the worst that will happen is they go home mad that one lady didn’t kiss their butt for serving a shitty burger, and that is their penance.

The great thing about non-assholes is that when you tell them the truth, they listen, even when it’s difficult to hear. It might take a few very uncomfortable conversations, especially if the situation you’re discussing is as serious as the one with Carrie, but a good friend will hear you and, along with some potentially hurt feelings, you give them the chance to empathize with you for once.

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