Dear E. Jean: I made the mistake of my life, and I want it fixed! I'm 27, and after six months of being showered with attention, sexy messages, and dinners, during which I was constantly told how beautiful I was, I gave in and slept with my boss (a 50-year-old charmer who all the girls in the company are absolutely crazy about, and he chose me!). But since then, he's been avoiding me. It's very uncomfortable. I love my job and I want to stay, but I feel like a fool! Should I tell him that his attitude hurts me?—Totally Lost It

Oh, he chose you, huh? And did you choose his leathery-ass skin? Did you choose all the barf-inducing moments during which he reminded you of your dad? What I don't get is that you're 27. You're young enough to realize that any man twice your age is sleeping with you not because he "chose" you but because he is on some level gross. And yet, you are old enough that if you were going to learn the "never sleep with your charming lech of a boss" lesson the hard way, you should have fucking done it already. How did you think this was going to play out? Like it does with all those other fiftysomething bosses and twentysomething assistants you see in the New York Times wedding announcements every Sunday? Anyway, he's avoiding you now because he's scared you're going to sue him for sexual harassment. I know you say you haven't told him so yet, but somehow he got the message that his attitude "hurt" you, and he's staying the fuck away. He probably thought you were one of those girls who knows the "rules" of this shit. I mean, I can't tell you I know the rules because for all intents and purposes the rules are to not have sex with boss/mentor dudes who are twice your age because they will invariably want to and that is really the only advantage women ever have in the workforce. So go, quit your job, find a new endearingly lecherous boss to "choose" you, and pretend you don't notice until you get a few more promotions.

Living Large
Dear E. Jean: I used to be pretty. I'm also single, 29, a physician, and haven't dated in five years. I suspect I know the problem: I'm overweight. I work out a ton, watch what I eat, and have been trying to lose 40 pounds for six years, but to no avail. Will I ever be cute again? Is it a mistake to hope? I'm terribly lonely because I've recently moved to a fabulous new city and don't know anyone. Should I try online dating? Or do I put everything on hold, finally lose the weight, and make a new start?—Pre-Fab

Stop working out. Seriously, why spend valuable time sitting there on an elliptical trying not to stare at your fatfat fat muffin top/upper arms/belly/whatevs whilst miserably assigning yourself a ranking somewhere near dead bottom of all the human cargo of the machines arranged around you, evaluating yourself for hours a week on the sole basis of the muscle tone of your exposed flesh — amongst people who probably think that is a decent way to evaluate people, no less! — when the whole time-eating process only ever results in making you hungrier faster? Ugh, fuck exercise. If you must do it, take walks outside. Listen to the news. Learn the quirks of your new city. Stop in a bar. Sit next to someone. Have bad sex. At some point it will get less bad.

Fate
Dear E. Jean: What happens when you can't get rid of your mistake? Long story short: I broke up with pseudo-boyfriend two years ago; we're both dating other people now, and we're both happy; but he keeps crossing my mind...and now, my path. Of all the people in New York, he's the one I always see. He's everywhere! We run into each other on the street, at cafés, at bars. Why?!? Is this some sort of wacko sign? I hope not!—Afraid to Leave the House

Too stupid to answer.

Tort Reform
Dear E. Jean: I'm a 22-year-old law student who's ended three serious relationships in the past two years, made numerous colossal blunders, and let a number of opportunities pass by.

The event that spurred me to write to you? My ex-fiancé is now engaged within six months of our splitting. The relationship wasn't healthy and I don't want him back, but it still burns. For some insane reason, it's made me wonder about a lot of my choices. I feel like I should have done everything by now. I'm walking around clubbing myself to death, and I don't know how to stop. I feel worthless. When I look at the past, even my successes look like failures. What's going on with me? How do I end this?—Inadequate, Desperate, and Lost

Yeah, I am not going to even try and give a shit about a 22-year-old.

A Tail of Woe
Dear E. Jean: I just signed a lease for a very chic apartment with perfect white carpets. My best friend is thrilled for me, and that's the dilemma. She goes everywhere with her totally horrible dog. I love my friend—and I adore dogs—but her little beast poops on couches, carpets, and beds everywhere he goes. And she thinks it's funny! In the past, I've allowed the animal in my home, risking tension headaches lest the little pest makes "mistakes" (and he usually does!). But, E. Jean, if this dog leaves a mess on my new floor, it will be the end of our friendship. How can I tell her that her incontinent darling is not welcome?—Going to the Dogs

Ooooooh, what to say to the girl who becomes BFF with someone so hysterically devoid of basic human consideration that she allows her tiny dog to defecate all over other people's belongings — and yet feels she must end the friendship once threatened with the possibility that her own uberchic white carpeting might become the repository for the same crap?

Ummmmm, three words: MySpace suicide clubs. I hear they're hot right now!

The Better Man
Dear E. Jean: I broke off a relationship eight months ago with a man with whom I shared many common interests and hot sexual chemistry; but our goals and values differed wildly. I've now met a man who's everything my ex is not—supportive, loving, thoughtful, sensitive, financially stable, and emotionally mature.

But though he seems to feel we're perfect for each other, our interests are very different, and I just don't have the hots for him. I long for the adventurous lifestyle and passion I had with my ex. Am I making a mistake? Am I wrong to focus so much on the differences with this new man? Will my feelings develop into something deeper?—Confused and Sleepless

Dear confused,
Have you ever told a dude, real casual-like, about the time you were date raped, only to watch his eyes go all big and horrified and you poor thing I honestly can't believe a man could be so coarse and cruel as to do that to anyone, much less you, because you are so wonderful and soooooo undeserving of such horror.... See, I always wonder about this. On one hand, it's a nice feeling. That guy probably won't cheat on you. That guy has a moral compass! On the other hand, does he have friends? Has he ever seen a movie? Does he have eyes? For centuries the advice industry has been hung up on perpetuating this bad boy/good guy partisan structure, mainly because a lot of girls simply fall for guys who treat them badly because, you know, they treat them badly. (What's wrong with them? If they can reform them they can feel superior to every inferior woman who was screwed over before!) But, you know, guess what! Human nature=nuanced! I say this a lot, but still. Anyway, I am not quite sure where I was going with this, but...

Oh yes, you. You broke up with a dude, EIGHT MONTHS ago. Why are you dating again? You are not over the dude with whom you allegedly shared so many "common interests", an "adventurous lifestyle" and "hot sexual chemistry" — or else i might have occurred to you that he is probably still pursuing those interests, and that lifestyle, and that chemistry. While you are pursuing a husband! Why? When you date someone who exposes you to new shit — books, ideas, travel, pastimes — the whole point of being single again is piecing together whatever it was you actually liked. Were you really into Zizek? Could you somehow reclaim for yourself that P.J. Harvey song you really loved? Because you should do all this and probably spend like six weeks crying about how worthless and empty and robbed of your identity you are. The dude will understand. He's "emotionally mature"!

The guy I'm seeing is incredibly well-endowed. I'm really nervous about sleeping with him; I'm afraid it will hurt. Should I say something about my fears?

Um, my first inclination is that if you tell this dude you are afraid of his dick you are going to be reenacting that scenario "Ohhhh I'm so scared your massive portion of manmeat is gonna hurty wurty my tight little child-gina" six months from now. But wait a second, how big is it that you have seen it, and yet have not put it inside you? My guess is if you have gotten naked with him and haven't, you know, done anything with his "member" and he hasn't acted like this was, like, weird at all, he knows what you're thinking and will be gentle. So drinking-game those nerves away and get fucking. Keep lube at the ready, but if you need it to get started, you're just not that into him. Which is just the thing: you're wasting time by worrying about this problem now. Down the road, if he's as big as you say, you'll have to deal with the fact that you both hate using condoms and that to blow him defies the Geneva Convention. So you'd better make some happy amorous memories while the relationship is still young and wet.

Why Did He Give Me His Business Card?

I met this boy at a party, and he seemed to be into me. He asked if he could give me his number and handed me his business card! What's up with that?

Why Does He Claim Not To Remember Our One Night Together?

A few weeks ago, I got really drunk with my best male friend. He confessed that he was attracted to me, and we ended up having sex. Now he is claiming that he was wasted and doesn't remember what he said, and he's been avoiding me. I just want things to go back to normal. What do you think I should do?

Ugh, I hate this. For one thing, he is lying, because when a person truly doesn't remember what happened when he was drunk and fucked his "best friend", he doesn't go and avoid the best friend because he doesn't know there is any reason to avoid her. Of course, that's another good reason God invented the "I don't remember anything I was drunk" excuse; so that people can go about their relationships like normal without having to submit to romantic comedy-perpetuated cultural mores such as "Sleeping with a good friend while drunk probably means there are unresolved feelings of True Love between me and good friend that would be scary to confront." But lying to you about not remembering and avoiding you simultaneously means the worst thing: he expects that you have succumbed to said romantic comedy cultural norms and that you, against all rational logic, feel there must be unresolved feelings of True Love between yourself and Mr. "I Can't Remember Why I'm Avoiding You." What a little jerk. Why are you friends with him anyway? Nevermind. Pretend you don't remember.

Should I Join Him In Playing Video Games? He Likes Them More Than He Likes Me...

My boyfriend just bought a PSP. Now it seems like he's dating his video games instead of me! Should I try to join in on his new hobby or tell him how I'm feeling?