Q: 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? —Love ’Em Tight and White
A: And the winner is... Brent Clements of Miami, Fla. For those of you who visited tightywhitiesarehot.com and voted, Brent was the guy in the white tank with the goofy smile. His winning picture is up now at the Web site. 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; second, because Brent’s boyfriend won’t be going to Vegas with Brent. “I’ll 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 along.”
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 500,000 votes — but he swears he didn’t cheat. “Someone was stuffing the ballot box for me,” he says, “but it wasn’t me!”
Finally, since Brent and his boyfriend broke up, Brent needs a date for our trip to Las Vegas. That person could be you. 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 email@example.com. Brent will look through the mail and pick someone to accompany him to Vegas. Good luck, guys.
Q: My girlfriend and I have been toying with the idea of marriage, but a few weeks ago I left the country and only 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. —Cheated-On Dude
A: First 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. 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 almost every guy she’s been with. 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 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, but Megan would sleep with at least two or three guys every year. 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!”) At first Zac was pretty upset by Megan’s ultimatum. “After 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. I would get so fucking horny and 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 — 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 see 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 think.”
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. If you’re crazy in love with her and you can stand the thought of sharing her, well, fuck what other people think. 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, 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 luck, COD.Contact Dan Savage at firstname.lastname@example.org