Miss Information

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I've lost forty pounds, but I still hate myself. What can I do?

by Cait Robinson

Have a question? Email Letters may be edited for length, content, and clarity.

Dear Miss Information,

About a year ago, I sent in a letter about my crappy dating situation and my struggles with losing my virginity. The advice was pretty sound: getting out and meeting people, trying a dating site or two, losing weight, and seeing a therapist. I followed it, and now I'm in a different position than I was a year ago. I'm in graduate school, I'm working full-time, I've joined a Muay Thai class, I'm dating online, and I lost about forty pounds.

The only problem: after about a year of therapy, I came to the realization that I do not like myself… at all. I'm generally pretty hard on myself, but I had a painful realization of how much I cannot stand about myself, even though I'm going in a pretty positive direction. I know that liking yourself and having positive self-esteem is essential before starting a relationship, but I can't seem to find the strength to do that for myself. That little voice in my head just turns everything into crap.

I guess the question is: exactly how doomed to be alone am I? I'm twenty-four, so yeah, I'm young, but I feel like a late bloomer. I've tried dating sites, and when I don't get a response, I feel pretty shut down and unable to go on. I wrap myself in work to avoid failing and flailing around in relationships. Am I doing everything wrong or is this just my fate? Am I damned to never have intimacy because of my intense self-loathing? 

— Man v. Self

Dear Man v. Self,

The timing isn't always right for romantic relationships; sometimes other pursuits take precedence. Some people stay single for months, or even years, while working on themselves. There's absolutely nothing wrong with that. You ask if you're condemned to be lonely — I argue that you're doing just the opposite. Stabilizing yourself is the best possible investment you can make into your future relationship success.

You've invested so much work into turning yourself around that discounting all of that progress simply because you don't see a relationship on the horizon is selling yourself short. We all have finite amounts of energy. You are totally allowed to pour your energy into yourself and only yourself right now. It may be no surprise that there isn't much left over for a relationship, and that's fine. 

It sounds like you're doing all of the right things; now you just have to keep plugging. A relationship will click when the time is right. Give yourself permission to put aspirations of a relationship on hold while you turn your energy inwards. And, for the record, the "late-bloomer/old virgin" stigma is outmoded and dumb. Any woman of substance will care far more about you — not to mention your radical self-invention and the strength of character that entails — than how many people you've slept with.

In the meantime, examine your non-romantic relationships. What kind of messages are you getting from friends and family? Are you being generally supported? If any voices are fueling your self-loathing — a nay-saying father, a subtly-undermining sister, or sardonic friends — examine those closely. When you're working so hard on yourself, it's especially important to limit any relationship that doesn't strengthen you. 

Many of us go through periods of cocooning before re-invention. Believe it or not, that discomfort might be evidence that you're on the right track.

Dear Miss Info,

I recently met a guy, and we immediately hit it off. He's not the type I'd usually be attracted to, but I guess that's what makes hooking up with him so exciting. We recently had a conversation about having sex (we've only gone to third so far) and he a dropped a huge surprise on me. Apparently, because he wasn't circumcised as a kid, it takes him much longer to orgasm than the average male. Now, maybe he was saying this to turn me on, but honestly, it's a bit intimidating. I haven't had sex that much, and it still hurts at times, so the prospect of having to go through forty minutes of semi-intense pain while he flops around on top of me is not too appealing. What can I do to make that experience less awful? Lube? Vicodin?

— I'm Pathetic

Dear I'm Pathetic (no, you're not),

A friend of mine, a chronic oversharer, had a similar problem to your dude. Then he got a dick piercing. He wanted it for aesthetic reasons, but says he's experienced much more sensitivity ever since. All right, problem solved!

Obviously, that is a joke. I'm not suggesting that anyone pierce anything, because… ouch. What I mean is, his "problem" is more common than he might think, and doesn't doom you to an interminable sexual encounter. My now-pierced friend confirmed what I already suspected: if you know it takes you a long time to come, you get creative. 

What will really save you here is communication. If he's paying attention, he won't be "flopping around on top of you" while you count the ceiling tiles. You two may be on different timetables, but that's something couples often have to work out in the beginning stages. Give it a shot. If it gets uncomfortable for you, back off from penetration and move to something else: oral, handjobs, mutual masturbation. The first few times, as with any time you sleep with someone new, may be a little awkward, but it's a matter of learning to read each others' bodies. You may learn that he needs a head start (oh, pun not intended), or that his longevity issue is really overstated, and that it doesn't turn out to be a problem at all. Ask him what's worked in the past, and plan on lengthier foreplay. Chemistry will surprise you, so don't believe the worst-case scenario.

It's great you're being proactive, but your half-joking questions — "Vicodin? Make this less awful?" suggest you're at least partially dreading the encounter. Remind yourself that you aren't in this alone. Sex shouldn't be you dosing yourself, taking deep breaths, then enduring the inevitable. Speak up if something is uncomfortable or not pleasurable, and trust your guy to pay attention and make adjustments. Nobody needs to lie back or think of England. If you think this is really how the encounter is going to play out — i.e. if you don't trust or like the guy enough to believe it'll be good — then maybe consider whether you want to do this at all.