Archive for October, 2009

The Halloween Charity

This question comes from Aaron in Reno, NV.  He writes,88622754

QUESTION: I’m a single guy, and I go through this problem every year.  I like to go Halloween parties with some very attractive women, but I always choose a costume that wouldn’t help me get laid.  For example, last year I dressed up as Mike Vick, and all of the women thought I was an asshole.  The year before, I dressed up like a drag queen and everyone thought I was gay.  What should I dress up as this year?  There’s going to be a lot of hot single women at this party on Saturday night!

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Halloween in Los Angeles

This question comes from Shawn in Dallas, TX.  He writes,79319890

QUESTION:  I’m a Texan, and due to an unfortunate work-related business trip, I’m stuck in your cesspool of a city this weekend (editor’s note: he’s referring to Los Angeles).  I’m not at all happy about it, but I am looking forward to going to a Halloween party on Saturday night.  I want to wear a costume so offensive and over-the-top that it will totally piss everyone off at the party.  Any ideas?  Oh yeah, and don’t mess with Texas!

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The Halloween Hater

This question comes from Michelle in NYC.  She writes,yankee

QUESTION: My husband hates Halloween and absolutely loves the Yankees.  As I’m sure you know, the Game 3 of the World Series happens to be on the same night as the holiday.  The problem is that I have four year old twin girls who love Halloween and they really want to go trick-or-treating that night.  Normally, I’d just take them out myself - but I broke my leg in a skiing accident last weekend.  Because he’s a lazy jerk, my husband made it totally clear that he’s not missing the baseball game for any reason.  So it looks like I have two options: Either I drug my children so they sleep through Halloween, or I rent a wheelchair so I can roll through the neighborhood with them.  What should I do?

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Degrees of Hotness

This question comes from Andrew in San Diego.  He writes,86542408

QUESTION: Trey, I need your advice on something.  One of my buddies just started dating this girl a couple of weeks ago, and she keeps talking about how “hot” she is.  I met her for the first time during happy hour this past Tuesday, and I don’t know if I’d say she’s “hot”…actually, I don’t know what I’d call her.  She’s definitely not ugly, but I need to know how to categorize her.  My buddies have been texting me to ask for a description, and I’ve got nothing for them.  Can you help?  Read the rest of this entry »

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How Do You Like Your Salad?

This question comes from Michael in Santa Monica, CA. He writes,medfrd0630

QUESTION: Hey Trey, here’s an interesting one for you: I met a girl a few weeks ago that is pretty freaky (definitely more freaky than that chick from the “Talk Dirty to Me” column from last week), and the other night she asked me to toss her salad. I’m usually down for anything, but I don’t think I could do that.  How should I handle it?

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The Long Road to Stardom

This question comes from Kathy in Wichita, KS.  She writes,85861571

QUESTION: Hi Trey. I know you live in Los Angeles and achieved some stardom there, and I’m thinking that I could move to LA to get a career in modeling. I’m 22, cute, funny, and I’m thinking I should move before the end of 2009. Should I do it?

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Talk Dirty to Me

This question comes from Larry in Los Angeles.  He writes,81783079

 QUESTION: Love your column, Trey.   I just started dating this girl a little while ago, and we finally started having sex.  The odd thing about her is that she says she can’t have an orgasm unless the guy she’s with talks dirty to her.  I guess I’m old-school, but I have no idea what to say to her without sounding like a complete fool.  Any ideas?

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Have a Gay Ol’ Time

This question comes from Jason in Boston.  He writes,57441602

QUESTION: Trey, I know that this story will be hard to believe for your readers, but I’m going to share it anyway.  I have a job with a boss that I absolutely hate.  He’s a total jerk with a raging Napoleon-complex.  Anyhow, I was about to head out to a party at a local nightclub last Friday night, but I forgot the tickets in my office so I drove there around 9:30pm to pick them up.  I couldn’t believe what I saw when I got there…

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The Other Swine Flu

This question comes from Phil in New Jersey.  He writes,88676250

QUESTION:  A friend of mine has the swine flu, and I’m concerned that it’s contagious.  I was planning on going to the Phillies NLCS game with him this weekend, and I don’t know if I should sell my tickets instead.  Any advice for me?

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Cheating 101

This question comes from Tony in Las Vegas.  He writes,sb10064861z-001

QUESTION: Can you define cheating for me?  I have two friends who are on the opposite end of the spectrum on this.  My boy Mike thinks cheating is anything that his wife does without clearing it with him first (talking on the phone, going to dinner with friends, etc.).  My boy Pete thinks it’s only cheating if you ejaculate inside of the woman.  For example, if you cum on the woman (her face, belly, etc.) it is not cheating.  Obviously, both of my friends are completely insane, but maybe you can you settle this once and for all.

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A Big Problem

This question comes from Ann in Los Angeles.  She writes,84951151

QUESTION:  I’ve been dating a guy for about 3 weeks now.  He’s amazing and I’ve found myself falling for him fast.  The problem is, I’m a prude.  I’m 29, and I’ve only had sex with one guy – and that was after dating him for over a year.  For some reason, I really want to have sex with my boyfriend, but I’m really worried about something.  When we were messing around last weekend, I saw his penis for the first time and it is absolutely HUGE.  I’m scared to death to have that thing inside of me, but I really like him and I know that he’ll be gentle.  Do you have any advice on how to take a large penis?

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Black Ice

This question comes from Jeff in Brooklyn.  He writes,hockey

QUESTION: I’m a black man and I met a beautiful black woman over Labor Day weekend.  We’ve been dating about a month now, and I found out something very disturbing about her.  She’s a die-hard hockey fan.  I mean, she LOVES it.  Have you ever heard of such a thing?  A black woman who likes hockey??  She’s been begging me to go to a NY Rangers game, and I think I might just break up with her instead.  What do you think?

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Make Love to My Wife

This question comes from Bill in Houston, TX.  He writes,IS098R7XB

QUESTION:  Trey, I need your opinion on something.  My wife and I are trying to find ways to spice up our marriage.  We’ve been together for about 9 years, and things have gotten kinda stale…especially in the “sex” department.  We are a white conservative couple in our 40′s, but whenever we watch sports together, she tends to find black guys very attractive (Terrell Owens, Allen Iverson, etc.).  So here’s my question:  I was thinking about opening up our relationship by watching a young black guy have sex with my wife.  There is a guy who plays basketball at the park near our house and I think he’d go for it if I paid him.  I think it would be exciting for both of us, and surprisingly my wife is totally for it.  Should I do it?

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Weekly Douche – Volume I

TREY SAY: From this point forward, I’m going to add the Weekly Douche section to my column.  Basically, it’s a description of the various douche bags I’ve had the pleasure of running into during my week in LA.  It’s my way of venting, and it’s therapeutic for me – so you’ll just have to deal with it.douchebag

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Man Up

This question comes from Matt in Upstate NY.  He writes,sb10065285bk-001

QUESTION: I have a 7-year old son who has come home crying almost every day from school for the past week or so.  He never wanted to talk to me about it, so all I know is that one of his classmates is bullying him.  His mother won’t get involved, so one day I decided to make a surprise visit to his school to see what’s going on.  To make a long story short, I found out that his “bully” is a 6-year old girl who calls him “stinky-face.”  I asked myself WWTD (what would Trey do?) and decided to ground him indefinitely until he “mans the hell up.”  I’m trying to decide what he can do to prove his worth as a man.  Your suggestions are welcomed.

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