He’s been on Gossip Girl. He’s done The Moth. And now, he’s taking questions. As the author of six books (most recently the genre-busting Gay Men Don’t Get Fat) and as the Creative Ambassador-at-Large at Barney’s, Simon Doonan knows a thing or two about a thing or two. Which is why we enlisted him to be our fashion advice columnist, lending much needed counsel to hapless souls in search of sartorial inspiration, diet tips, and penis euphemisms. Just don’t say we didn’t warn you.
Dear Simon, What should I wear to attract hot guys in low-end restaurants? (I’m talking Gray’s Papaya-level low-end)
I think you should dress like yourself. If you disguise yourself as a blue-collar gritty manual laborer, you know you are going to run smack into all your antique-dealer friends who will start mocking you and asking probing questions about your new oily dungarees.
Dear Simon, I have a date with a really hot girl tonight, and I want to dress to give the illusion of having gone up a cup size. How can I organically achieve this?
It‘s all about arching your back and doing the occasional shimmy. Maybe watch an old Sophia Loren movie to get some body-language tips.
Dear Simon, I’ve been told that my vagina tastes like moth balls. I am politically opposed to douching. What should I do?
Re-examine your politics. How about an organic sustainable grape-seed lesbo-douche?
Dear Simon, My girlfriend is dead set on buying us matching union suits. Is this a comment on our relationship?
In a relationship it’s important to say “YES!!” to everything. Sorry.
Dear Simon, Last week, I received the worst insult ever when someone came up to me in a bar and accused me of dressing like Alan Thicke on Growing Pains. How can I correct this?
Clearly your current Thicke look is getting you some attention. Stick with it. Attention is important for your spiritual well-being.
Dear Simon, I’m dating this really amazing guy but he likes to use ketchup as foreplay. How can I gently break it to him that I find this disgusting?
It’s your fault. If you were smart you would have nipped this in the bud and claimed to have “a vinegar allergy” the first time he pulled out the ketchup bottle. Now you have to suck it up, metaphorically.
Dear Simon, I am a joke writer who has somehow run out of hilarious penis euphemisms. Please help me out!
I share your pain. I ran out of them years ago. Why not just make up some new penis names (like the way they make up new names for prescription drugs). Examples: donglage; protrick; scrabtube; laberonomy or parkatoblance.
Dear Simon, I am an easily offended person. The other day, my sister told me that I look fat in colors other than black and I called her a fat castrated whore. How can I mend this rift between us? Also, how can I look skinny in colors other than black?
Vertical stripes. Re your sister: a relationship which is characterized by free-flowing insults is a healthy relationship.Explain this to sis and then have at it!
Dear Simon, I have very lopsided shoulders. Which Winter line will cater the most to my shoulder-evening needs?
Avant-garde fashion is your answer. In a Comme des Garcons cocoon, your physical idiosyncrasies will appear secondary to the overall insanity of your appearance.