Archive for September, 2009

This question comes from Kate in Orange County, CA.  She writes,

QUESTION:  Hi Trey, I need your help with something.  I’m a 19-year old white girl and I’ve been dating my boyfriend for about 4 months now.  My family is ultra-conservative when it comes to everything (politics, sex, etc.), and I don’t know how I’m going to break the news to them that I’m dating a 26-year old black man.  He’s a great guy, but he’s very urban (he did some time in jail, has numerous tattoos, works at a supermarket but is an aspiring rapper, etc.).  My parents’ 25^th wedding anniversary party is going to be held at the local Country Club on Saturday, and they want me to bring my boyfriend (they don’t know that he’s black).  They are so closed-minded, and I know they’d kill me if I brought him along.  What should I do?  Read the rest of this entry »

This question comes from Mike in Los Angeles.  He writes,

QUESTION: My girlfriend used to have no boobs whatsoever.  Since I have a lot money, I always used to tell her that I’d finance her breast implants.  Finally, after about a few weeks of me asking – she took me up on the offer and got some large C cups.  She looks amazing, but the problem is she broke up with me as soon as she recovered from the surgery and is dating someone else.  Should I sue her for the cost of the surgery?  Should I beat up the dude who stole her from me?  I demand advice! 

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This question comes from J.D. in Denver.  He writes,

QUESTION: I’ve been dating an exotic entertainer for 4 months.  She’s 30, beautiful, and I think that she loves me, but her quirky trait of undressing for men bothers me.  I’m going to introduce her to my parents this weekend, and I think I’m going to ask for her hand in marriage shortly thereafter.  What do you think?

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This question comes from Debbie in Los Angeles.  She writes,

QUESTION: I’ve been dating a really good-looking guy (he looks like the Wal-mart version of Vin Diesel) about for about 6 weeks now.  He says that he’s a really good basketball player who was once offered a scholarship to play at Cal State Fullerton, but decided against it in order to focus on 100% on academics.  Anyway, he started playing in a men’s basketball league a couple of weeks ago, and I always ask if I could watch him – but he keeps saying no.  His excuses are lame, too – like “there will be no place for you to sit” or “it gets really hot and stuffy in the gym, and you’ll be uncomfortable.”  One day, I just decided to show up at one of his games without him knowing.  All I can say was it wasn’t pretty. .. Read the rest of this entry »

This question comes from Andrea in Los Angeles.  She writes,

QUESTION: I went on a blind date with a guy over the holiday weekend.  We had a wonderful dinner together, took a romantic walk down the Santa Monica pier, and he gave me a nice good-night kiss.  So what’s the problem?  Well, after the kiss he said “I think I’m in love with you.”  What the hell?  Who does that??  I only knew him for 3 hours at that point.  Some of my girlfriends think it’s cute.  Anyway, he’s called me 15 times since the weekend, and he’s not taking the hint that I’m not interested anymore.  Help!

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This question comes from Patty in San Francisco.  She writes,

QUESTION: I am writing to you for advice on this issue because first and foremost, you are brilliant, and you are the only person who can help me through this hell hole that I am in.  My boyfriend’s name is Ike. We’ve been in a quasi-relationship for a couple of years now.  I call it “quasi” because he has cheated on me a number of times, doesn’t have a job, and l take care of most of his financial needs.  He has slept with my mother, and my sister several times (and once, at the same time).  Believe it or not, it gets worse…much worse. Read the rest of this entry »

This question comes from Trisha in Santa Monica, CA.  She writes,

QUESTION: I’m a college student that met a really cool guy during a summer internship in LA.  Problem is that he lives in San Diego.  Yes, I know that LA and SD aren’t that far apart but we’re both too busy to see each other as often as we’d like to.  Anyway, lately he’s been asking me to send him some naughty pictures of myself to “tide him over” during those days that I’m not around.  I’m a little hesistant because he lives in a fraternity house with 25 guys, and I know how those boys can be.  What do you think I should do?  Do you think he’d show the pictures to his friends? Read the rest of this entry »

This question comes from Jenny in Philly.  She writes,

QUESTION: Can you help me to understand something?  What’s the big deal with Fantasy Football?  I think I’ve seen my boyfriend twice in the past 3 weeks.  When I do see him, his head is buried in his laptop looking at ESPN.com.  All he’s been talking about lately is if he should draft Mike Vick in the 3rd round.  I have no idea what the hell that means, but it sounds stupid.  Is this a guy thing?  Or is my man a complete idiot?

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This question comes from Ben in Atlanta.  He writes,

QUESTION:  I just broke up with my girlfriend about a month ago.  Now I can’t help but see her everywhere I turn.  She’s on Facebook and her profile picture is of her making out with some dude.  It’s killing me, and I think I want her back.  What should I do? Read the rest of this entry »