Top 10 Questions We Hope Nobody Ever Has to Ask Us Again

We recently published a list of the top 25 questions we get asked over and over again. We’ll probably keep answering those sorts of questions until we’re old and wrinkly and everyone thinks it’s either cute or hilarious or gross (or all of the above) that two old biddies like us discuss porn and strap-ons and friends with benefits. Questions like those remind us why we’re here, why we’ve been doing this for nearly fifteen years, and why we keep on doing it even when it doesn’t pay as much as we’d like it to.

But there are some questions we hope we never receive again. Questions that make our hearts sink because they’re unanswerable or depressing or horrifying — or simply because they make us feel useless and unqualified. And so far as we could tell, all of the questions were sincere cries for help. In most cases, we served as nothing more than an unoccupied confessional booth — after all, so many of them qualify as a sort of Sophie’s Choice of sex — and in most cases, we were sincerely sorry about our inability to help.

Here they are, the top 10 questions that reminded us what a bad, mad, sad world it is out there:


1. Help, I’m too medicated to enjoy sex but too depressed to go off my meds.

2. I love my spouse and my children but I’m no longer in love. Should I stay or should I go?

3. I hate the way my fetish makes me feel, but I can’t feel anything in bed without it.

4. I was raped as a teen, will I ever enjoy sex again?

5. My sister and I are in love with each other. If we use birth control so she doesn’t get pregnant, is this really so wrong?


6. I work in a morgue. I’m not asking you to judge me, and I swear I’m not making this up, I was just curious if it’s possible to contract an STD from a corpse?

7. I’m cheating on my partner, but let me tell you why I am justified in doing this so I can feel better about myself…

8. My golden retriever really seems to enjoy pleasuring me. Is it okay if my husband watches?

9. Does this look infected?

10. Does this look like an average-sized penis to you?



  1. Ok, we tried to fix the post, we hope it now does a better job of conveying what we really meant to say!

  2. We’re so sorry about the way this post came across! We did not intend the “subtle mockery” at all — we sincerely believe that every single one of these questions was a true cry for help. We know that some of the questions read like jokes, but if you could read the original, LONG letters we received, you’d realize they weren’t joking at all. (We actually receive surprisingly few joke/fake questions — we could probably count them on one hand in the entire 15 years we’ve been writing an advice column.) As we said, the questions were depressing AND/OR horrifying. But perhaps we can make the distinction (horrifying vs depressing) more clear…we’ll take another look at the post now. Thanks again for your honest feedback, we appreciate it.

  3. I don’t get this. Your second paragraph is about empathizing with the questions, as you find yourself unable to answer them or because they’re too depressed, and then the list you provide is jokey. There’s a subtle mockery happening in how you word the questions, which contradicts how you frame the questions. It’s no laughing matter when somebody loses their sex drive due to meds but are unable to relinquish the meds. And yet it’s put up against a necrophilia joke and a handcuff joke.

    It’s not that I’m offended; I’m just utterly confused by the tonal variance.

  4. Good point f, we’re so sorry about that! We changed the headline of the post, we changed the intro text a bit (for the non-lazy readers), and we replaced #5, too. Better? Thanks for keeping us on our toes!

  5. I… Er… OK, you do introduce this list with a little text that has empathy. I really hope other readers didn’t do like I did, which is to only read it after getting depressed by the list that seemingly (if you’re too lazy to read the intro) puts item 1 and item 5 on the same footing.
    It makes me a bit uneasy if I imagine raped teenagers who can’t seem to enjoy sex be as lazy as me reading this list.

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