have a problem that I have to deal with and I don’t know who
else to turn to. My girlfriend and I have been toying with
the idea of marriage, but a few weeks ago I left the country,
and I got back yesterday. She told me that she cheated on
me twice with two different guys when I was away and that
she couldn’t really help it because she has cheated on almost
every one of her significant others. Now here comes my problem:
I don’t want to break it off with her. She is the most amazing
woman in the world! But she doubts that she could ever stop
cheating. I don’t know what I should do. She says she only
did it because I left and that she missed me and wanted to
feel special even if only for a moment, and I believe her.
Sorry this letter is disorganized and rambling, it’s been
a hard day. Please help me, Dan.
of all, that I-only-did-it-because-you-left-and-I-missed-you-and-wanted-to-feel-special-even-if-only-for-a-moment
line is a crock of shit. Christ, I hope you didn’t
fall for that.
As for the rest of your letter, here’s the problem: You love
this woman, she cheated on you, and she is going to cheat
on you again. To her credit, your girlfriend put all her cards
on the table: She’s messed around on every guy she’s been
with and, what’s more, she “doubts” she’ll ever be able to
stop cheating. Let’s read between the lines, shall we? When
she says she “doubts she’ll ever stop cheating,” what she
means is, “I like cheating, it turns me on, and I have no
intention of ever being faithful to you or any other man.”
Is she a terrible person? No. Should you dump her? Depends.
She leveled with you—which is more than most serial adulterers
ever do—and now you get to make an informed decision: Do you
want to be with the most amazing woman in the world, COD,
even if this amazing woman cheats on you with some regularity?
Or do you want to dump her and go find someone less amazing
but more faithful?
Reading your letter reminded me of a desperately sexy guy
I met last year when I was doing some research for my next
book. Zac—an amazingly good looking 28-year-old guy—was going
out with a girl named Megan, a 32-year-old lawyer. After they
had been dating for six months, Megan laid her cards on the
table: As much as she loved him, Megan could only be with
Zac if she could have sex with other guys once in a while—not
with tons of other guys (we’re not talking Catherine
M. numbers), but Megan would sleep with at least two or three
guys every year. But there was more: Despite the fact that
she had no intention of being faithful to Zac, she could only
be with him if he promised to be faithful to her. Was
Megan being unfair? Yes. Did Megan have a double standard?
You bet. Was she doing the right thing by Zac? Absolutely.
She told him the truth: Be with her and be cheated on, or
find someone else. Most men would’ve walked out the door (“She
can cheat on me but I can’t cheat on her? Fuck that!”), and
at first Zac was pretty upset by Megan’s ultimatum.
the shock wore off,” Zac told me, “I admitted to myself that
I didn’t really want to sleep with other women, so I told
her OK.” He doesn’t get jealous? “I did at first, but when
she did sleep with other guys, she would come home and tell
me about it, and I would get so fucking horny-slash-angry
that we would have the most amazing sex. Pretty soon I wasn’t
angry when she fucked around, just horny.”
It was a good thing that Zac was just horny by the time he
proposed to Megan a year after her ultimatum. She agreed on
one condition: The mutual friend who introduced them, a man
with whom Megan regularly “cheated” on Zac, would be Zac’s
best man and on their wedding night, Megan would
fuck the best man, and not the groom. “That Zac agreed
to it kind of sealed the deal for me,” Megan told me. “I knew
that he was the right guy for me.”
Ah, love.” Our deal is weird,” Zac told me when I called to
how things were going. “She has total sexual autonomy but
I don’t have any at all. I guess I’m submissive to her, even
if I don’t have to eat dinner out of a dog dish or anything
freaky. Guys who read this will think I’m a freak, but it
turns me on and it turns her on, so fuck what other people
So what’s the lesson here for you? If fidelity is important
to you, break up with this woman immediately. She may be amazing,
but she’ll never, ever be faithful. But if you’re crazy in
love with her, and you can stand the thought of sharing her,
well, fuck what other people think. And maybe with time and
reasonable safeguards, you guys can turn this amazing woman’s
need to cheat on you into something that enhances your shared
sex life, just as Zac and Megan have. Unlike Megan, however,
your girlfriend may agree to a co-equal, even-steven open
relationship; perhaps you could go to swinger’s parties together,
where she could screw around with other guys while you mess
around with other women. Or if swingers’ parties hold no appeal,
you would be free to cheat on her when you go out of town
since you know for a fact she’ll be cheating on you. Good
Dan! Whatever happened with the tighty
whities contest? Two weeks ago you said you were having trouble
contacting the winner and then no update since. What gives?
‘Em Tight and White
the winner is . . . Brent Clements of Miami, Fla.
For those of you who visited the tighty whitiesarehot.com
and voted, Brent was the guy in the white tank with the goofy
smile. His winning picture is up now at www.tightywhitiesare
Brent’s picture was entered in the contest by his boyfriend
without Brent’s consent. Brent and his boyfriend broke up
during the contest, which is too bad for Brent’s ex-boyfriend.
First, because Brent’s fucking hot, and second, because Brent’s
boyfriend won’t be going to Vegas with Brent.
get him a nice present,” Brent told me when I finally—finally!—got
him on the phone. “But I think it would be awkward if he came
Here are some fun Brent facts: Brent grew up on a dairy farm
in Wisconsin, he works in mergers and acquisitions, he’s gay
as a goose, he says he’s shy, and his big unrealized fantasies
are taking part in a safe orgy and getting tied up
sometime. Brent prefers TWs because boxers bunch up, and he
intends to wear TWs for as long as he’s thin. Brent got a
half a million votes, but he swears he didn’t cheat. “Someone
was stuffing the ballot box for me,” he says, “but it wasn’t
Finally, since Brent and his boyfriend broke up, Brent needs
a date for our trip to Las Vegas. That person could be you.
No, no, no: It’s not another contest. God fucking forbid.
If you want to be Brent’s date in Vegas, all you have to do
is e-mail your picture, a nice letter, and three references
to firstname.lastname@example.org. Brent will look through
the mail and pick someone to accompany him to Vegas. Good