Dear Holly, I just discovered that my boyfriend secretly collects what appears to be used underwear. Maybe from past hookups or ex-girlfriends? He keeps them in a box in his closet like some kind of bizarre time capsule. They’re like, obviously unclean. He doesn’t know I know. I was putting away his laundry, and I found a random box. I should have left it alone, but I opened it. I couldn’t help it. It was like I was under some kind of spell or something. Do I pretend I never saw it, or is this the kind of thing you absolutely have to confront?
You’re right. You shouldn’t have opened the box. Pandora’s secret pantie box, really. We should never snoop, because some things really ought to remain unseen and I would venture to bet that the image of other people’s dirty underwear will forever be seared into your psyche. Your boyfriend deserves to have a private life. We all have embarrassing stuff we don’t want our partner to know about. We all have “a box.”
That said… WHAT THE FUCK?
I’m sorry but ew. No, really, I am SO SORRY. Are you okay? What the hell is wrong with men? Why are they so disgusting? And how do you know these undies belonged to people he knew? He could be buying them on the internet. I know lots of girls who’ve mail order sold their dirty socks and underwear (who me?)
Okay. Deep breath. Now that I’ve got that out of the way, we can get into it. This is where I need you to look, and I mean really, truly magnifying-glass, fine-tooth-comb search for other clues in your relationship to better understand what this could mean.
What kind of man is your boyfriend? How does he treat you? How does he make you feel? Is he kind, generous, sensitive and honest? Having a box of underwear doesn’t necessarily make him a liar, or untrustworthy. Some men do have fetishes and that doesn’t mean we should immediately vilify them. Or like, how women may collect old love letters—which by the way, I’d be humiliated if my boyfriend ever found—men have collections too.
Are there other red flags? In what other ways is he secretive? Is he sneaky? Can you look in the mirror, stare into your own eyes and say with absolute certainty that you trust this man? Because if you can, and you do, and you’ve spent enough time with him to KNOW that you know him well, then you may want to try to let the dirty undies box go. Tuck it away in some deep corner of your mind or just have a good laugh over it and how ridiculous men are. Otherwise, he may lose his trust in you, you little snooper.
But if your gut tells you there’s more to this story, more boxes to find, more secrets to unearth if you just keep digging, then by all means… get out your shovel and DIG. This dirty discovery may be the best thing to ever happen to you.
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Dear Holly, How long should a man go down on a woman?
As long as it takes, my friend, as long as it takes. He should not stop until she’s shaking uncontrollably and yells, “Okay, enough, enough, stop, stop, stop.”
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Dear Holly, I have an autoimmune disorder that affects my skin. How and when do I let my partner know?
In an age of oversharing, it’s almost as if keeping any personal information personal may be punishable by a thousand lashings. Emotional dumping tends to feel almost obligatory. Though I am starting to understand how important it is to reveal yourself to people slowly. To take your time to get to know people. Don’t be spilling the beans on every little detail of your life and self, in an effort to rush closeness.
Closeness should organically unfold in its own divine timing, which is different for everyone in every relationship. There is no specific time, no magic number as to when and how you should say this or that. Most importantly, trust and vulnerability should be earned. Obviously, this is something you feel sensitive about or you wouldn’t have written in. And delicate issues are vulnerable. You don’t owe anyone an explanation of your personal business, until you’re ready and comfortable with them.
This is why rushing into sex can be really confusing and dangerous. It forces intimacy very quickly and you often have to work backwards, getting to know if someone deserves that level of you, after you’re already in too deep. That said, we get horny and things happen and that’s okay too!
Because I don’t know what this skin condition is, how it affects you and how it might affect someone else, all I can say is; be responsible and conscientious of any potential partners. Also, be gentle and considerate to yourself. Love yourself. Protect yourself.
And finally, the right person will be in your life because of YOU. The right person won’t give a single fuck about your skin, other than wanting you to feel good inside of it.
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Dearest Holly, I am writing to seek your perspective on a situation that has become increasingly difficult to navigate. My new partner is a skydiver. She belongs to a tribe of people who have organized their entire lives around the pursuit of terminal velocity. It is a totalizing dedication, carrying the weight and intensity of a profound addiction. I want her to thrive, and I know this is what makes her feel that way. But the reality of what she does is horrifying to me. I am struggling to find the line between supporting her happiness and the very real fear that I will lose her to the sky. I would value any insight you have on how to reconcile these two truths.
The words profound addiction really stuck out to me, and I struggle to get past the weight and meaning they carry. Because a junkie or an alcoholic will explain to you with very straight-faced logic why they need their fix, why it makes them happy or helps them thrive. Or they’ll be in total denial about it.
Either way, they’ll find a way to claim that what they’re putting their total dedication into makes sense. And for you, standing by and watching someone potentially hurt and endanger themselves makes you… well… to be blunt… a co-dependent enabler.
You can’t change someone. Sorry, but you can’t. The only thing you can change is you, and the way you react to things. What makes you willingly enter a relationship with someone who is jumping out of airplanes, risking life and limb in the pursuit of terminal velocity? What make you think being attached to someone who has a death wish—or at the very least, a willingness to die—is a good idea?
Get your head out of the clouds! Are you addicted to this person? To the push/pull of unavailability? Because committing to someone who has one foot literally out the airplane door is a sign that you should look within, to see where you’re unable or unwilling to keep your feet on the ground.
Need Advice? Email: askholly@playgirl.com
*I am not a doctor, therapist or professional counselor. This advice is for entertainment purposes only.
Holly Solem is a writer living in Los Angeles, CA. Read her Substack, HollyWould, watch her internet series, Manthropology and follow her on Instagram!


