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Dear Captain, et al, and Awkardeers,

I have searched the archives and not seen anything like my current conundrum.

Cliffnotes: Former partner at the law firm where I am an associate, Jim, left the firm last year. We worked together for approximately a year, during which time he took lengthy FMLA absences. I haven’t spoken to him in the year since he left unless he dropped by the firm to see the senior partner about something. I had heard a rumor Jim was into BDSM, but gave it very little thought. (Whatever floats your boat, no skin off my nose).

Cut to last Friday. He Facebook messaged me asking if he could ask me a question. I thought it would be firm-related, so I said sure. He said nevermind. Two days later, a mutual friend (Sharon) asked if I’d be interested in entering a D/s relationship with Jim. She made the request at his behest, she said. Sharon described it as, “You let someone pamper you and you belittle them.”

I’m not into BDSM, but in my opinion that’s not the issue. This is such a breach of boundaries and professionalism that the more I think about it the angrier I get. We are not friends, we don’t interact socially, and he leaped over several levels of personal intimacy even making the request. Even though Sharon said “Nothing sexual,” to me that’s still a request for intense intimacy.

So, to the question. Do I say something to him? I interact with him professionally now and then. Do I tell him this was inappropriate, rude, and objectifying, or do I write it off and hope it never comes up again? (I told Sharon to tell him “No.”)

– I’m Not Yer “Queen”, Pal

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Dear Captain Awkward,

I hope you can help me with coming up with a script for an awkward conversation that needs to happen. Here’s the situation:

My husband and I (!!!) got married (!!) on Saturday. It was amazing in every way except for one—we made a guestbook for people to sign. The guestbook was a photo album of us and we had pens for people to write their best wishes for us in it. Most people wrote lovely things, and a few people cracked some funny jokes in it that I know we will enjoy looking back on. One person, however, was immature enough to draw a penis spurting cum all over my husband’s face. In our wedding guestbook. That our parents and grandparents are going to look through, and our kids one day (should we be so lucky).

We have a witness to the penis-drawing act, so we know who did it, and I can’t say I’m surprised. Husband and I would like to tell this person how the penis-drawing-on-his-face made us feel; namely, that it hurt our feelings that she did this and it made us feel that she doesn’t respect us. It makes me regret that we invited her to the wedding, but I’m trying not to think about that since it’s in the past and I’m still trying to maintain my zen-bride mentality which has served me well so far. Husband is closer to this person than I am but I am the more confrontational of the two of us, and he has more to lose in the confronting, being closer to her and to her partner, who is a particular friend of my husband’s.

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