DEAR SUGAR, The Rumpus Advice Column #43: Unrolling


Dear Sugar,

I’m a fan of the Rumpus, but tonight was my first time reading Sugar. I was so fascinated that I read all of your columns. You’re an incredible gem of a writer and human being. You exude so much kindness and wisdom, yet you write so well and with so much wit. When your identity leaks, I’m reading your whole bibliography (even your earliest, less polished work). Please let me be your servant/intern for a year if my life doesn’t work out.

Anyway here it is: I’m a nearly twenty-three-year-old man. I’ve never had any kind of sexual intercourse. I haven’t dated other than in high school, and those were not what I would call “relationships.” I haven’t even been in the presence of a half naked person to whom I’m attracted to until fairly recently. Several circumstances contributed to this state of affairs: I was an overweight child, my mother was very protective and sexually repressed, I was depressed for a long while, and I never had any sexual confidence.

My life has been quite a mess until the last two years when I figured things out. I have just traveled across the country to discover myself for the past eight months (with the prerequisite despair, almost suicide, redemption, strange new friendships, broken promises and back stabbings).

I have it all figured out now, except for love and lust.

I just moved to a new city. In the eight months that I was traveling, I let go of my self-hatred and also several pounds. I gained confidence in my body, some new tattoos, and grew long colorful hair and some muscles. Since I’ve been here, I’ve been actively trying to get myself laid or to experience as much sexual activity as possible. The results have been several hot make outs (a first) with women who are all too drunk (in my estimation), some of whom I like more than others. They all rejected me in one way or another when they got sober though.

I have had some epiphanies in the past week since I’ve taken some drugs (also a first) and went through the high and low cycle. I’m a romantic, and I don’t actually enjoy making out in public. Drunk people will usually want what they want when they’re drunk only while they remain drunk.  I want meaningful companionship and friendship. I also want sex of various forms. I want the two in the same person. To find that one person will require effort and dating and not just picking out drunk horny people.

I’ve been told that I’m sexy/hot various times since I’ve come to this new city, which has never happened before. The possibility of sex is screwing with my head. I’m thinking that if I feel used after I have meaningless make outs and petting, then I’ll probably feel the same after meaningless sex. (However, I feel no anxiety regarding any new sexual activities, as I’ve studied everything on the subject to the finest details in the past ten years.) I have met a couple people whom I would like to get to know better and maybe ask out. I also would like to just finally get laid and explore my sexuality. I really don’t know if I should:

a) Pursue sex where people imbibe alcohol.
b) Pursue romantic relationships with people I’ve just met in the city.
c) Pursue casual dating through Plenty of Fish.

I’m lying low right now; my decision awaits your wisdom and kindness.

Young in Lust & Love


Dear Young in Lust & Love,

Every time I read your letter I’m filled with a mixture of amusement, glee, wonderment, and tender maternal ache. You want to be my “servant/intern” for a year if your life doesn’t work out? That’s lovely, sweet pea. Trouble is, all of my servants are people whose lives have worked out, so let’s whip you into shape in hopes that you’ll someday qualify for the gig.

Your letter is long and complicated and sweet, but my answer is short and simple and sharp: it’s high time you get yourself laid, honey bun. And laid and laid and laid and laid. Do it bad. Do it good. Do it with drunk people and sober people. Do it with all your heart and only your body. Do it with people who stimulate you intellectually and sexually and bore you to shreds; with people who remotely piss you off and kinda sorta remind you of someone you used to know. Do it with strangers you met two hours ago and people you knew since you were twelve. Do it on the beach and behind a tree and while pressing someone up against the kitchen sink and so hard on the bed that when you’re done the blankets are nothing but a tangled mountain on the floor.

Just stop thinking about it and do it. Thinking about it too much seems to be a pattern in your life, a cocoon of doubt and trepidation that you’ve woven from your anxieties and sorrows. It’s a pattern I see you clinging to even now, as you simultaneously overly-analyze your dating options while claiming that you’d like to “just finally get laid.” Break the pattern, hon. It isn’t serving you any more. You asked me to choose one among your list of options: a, b or c. But one isn’t enough. For you, right now, I choose all three.

The rules of decency and respect and loving kindness we adhere to in Sugarland still apply. I’m not suggesting you become a wildly promiscuous fuck machine, though becoming a wildly promiscuous fuck machine can be an enlightening experience (trust me: Sugar knows). Nor am I saying you shouldn’t eventually ponder the big questions about love and sex and romance. Rather, I’m suggesting that right now the most important thing for you to do is to work in opposition to the instincts that have led you to this place in which a vital part of yourself is like a starved little monkey in a box.

Feed the monkey. Of course you “want meaningful companionship and friendship” and “sex of various forms” and you “want the two in the same person.” This is what we all want, darling. But there is time for that. You don’t get it right out of the gate. You don’t get it by hemming and hawing and making a, b or c lists before you’ve even been “in the presence of a half naked person” to whom you’re attracted. You get it by getting it and seeing how it turns out. By taking it all off and facing your anxieties about sex that have bound you up for so long.

It’s time to unbind, my innocent little peach. It’s time to evolve.

I want you write that word on a piece of paper and tape it to your bathroom mirror. Evolve. Every time you look at yourself say the word out loud. Evolve. It’s one of my favorite words. It comes from the Latin evolvere, which means to unroll. I hope when you say that word out loud to yourself you’ll imagine this time of your life as a great, brave unrolling.

Of all the obligations we have to ourselves, I believe that evolving is the most vital. Unrolling is at the very heart of the most important work we have to do. And though that unrolling means something different for each one of us, it essentially means releasing whatever it is we’ve kept bundled into the cocoon. For you, right now, it means to open wider, to risk harder, to reach less carefully, to taste more freely, to add the letters beyond a, b and c to your list and to work your way all the way down through z.

When you get there, send me your resume.