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20 Questions for Miss Howard TV

What’s your hometown and where do you live now?

My hometown is New Windsor, NY and recently I just moved back there after graduating college in Orlando, Florida.

What do you do from 9-5?

I’d like to be an on-air personality- so I mostly go to castings, auditions, shop, and run errands.

What do you do after that?

Well a few nights out of the week I work at a restaurant and the other nights I hang out with my boyfriend and go out with my girlfriends.

Congratulations, you are the first blonde Miss Howard TV. Do blondes really have more fun?

Being blonde is being apart of American Tradition.  I love being blonde and would never ever have a different color hair.  Blondes definitely without a doubt have more fun and I am so honored to be the first blonde Miss Howard TV!! 

Why do you like Howard Stern?

Howard is one of the hardest working men in this industry.  He started from nothing and worked his way to the top.  I graduated from college with a degree in Radio/Television and I admire his ambition, drive, and fearlessness in an industry which is very hard to make it in.

What do you find sexy in a man?

I’m very attracted to guys who are hardworking and calm.  I also tend to fall for bad boys and guys with dark hair (like my boyfriend).

If you could have sex with someone on the Howard Stern Show, who would it be and why?

I don’t believe in having a relationship with someone you work with and don’t have any feelings toward anyone on the show, but I do have a special place in my heart for Benjy J.

What’s the best way for a guy to pick up a hot chick like you?

There’s really no right or wrong way.  Just be yourself and don’t be shy.

What are some things that instantly turn you off about a guy?  Give us some tips…

One thing that turns me off INSTANTLY is when a guy starts talking about all the money he has or how successful he is.  I’ve been a lot of places and seen amazing things and contrary to what a lot of people may think nothing materialistic impresses me.  I also don’t like guys who are over-stimulating and very in your face.

Where’s the strangest place you’ve ever done it?

Well considering I’ve had a long term boyfriend…you could only imagine the places.

Have you ever had a lesbian experience?  Please explain…

No, and I’m not really into that.

Would you date a really nerdy guy… like J.D. from the Stern Show?

Maybe… just as long as he didn’t talk about money.

Howard TV viewers may recognize you as Benjy’s choice for the Hottest Regular Chick contest, where we found out you are Tommy Hilfiger’s niece.  What are some of the advantages or disadvantages of having a very recognizable name and a famous uncle?

Unfortunately the disadvantages balance out the advantages.  On the positive side, I get invited to amazing parties and get taken on fabulous vacations.  Also I have a really great extended family with lots of fun cousins.  On the negative side, a lot of people just refer to me as Tommy’s niece or “Hilfiger”.  Also, people think the only reason why I have nice things is because Tommy buys them for me when in reality my dad supports our family and works hard to give me those things.  The biggest disadvantage is when people are shocked that I’m working a normal job and can’t believe that I don’t get things handed to me.

What’s your best physical feature?  Why?

I like my eyes.  I’ve always been complemented on them ever since I was little and everyone always thinks I’m wearing colored contacts.

Are bigger boobs in your future?  Why or why not?

As of right now everything seems to be going pretty good for me considering what I have.  As for the future, you never know what it holds for you.

Have you ever had a threesome?  If so, tell us about it…

Nope.

Where do you see yourself in 20 years?

Hopefully successful in the entertainment industry, happily married with kids, and healthy.  Also I want to be a hot M.I.L.F.

Do you think being a hot chick makes life easier? 

It definitely doesn’t make life harder.

What’s your worst vice?

I would have to say it is being a perfectionist.  Also I’m a bit of a neat-freak which I’m sure my roommate can vouch for.

What’s your underwear of choice…thongs, bikinis or boy shorts?  Please… tell us why.

Nothing.  If I had the choice I wouldn’t wear any underwear and I usually don’t. 

Miss Howard TV Blog

Being Miss Howard TV for August 2007 has been one of the best experiences of my life so far.  Ever since I graduated college in May everything in my life has been happening so fast.  Here’s how it all started… 

At the beginning of June I was going into a restaurant in Times Square to apply for a job.  Outside of the restaurant Benjy approached me and asked me to appear on The Howard Stern Show as his contestant for The Hottest Regular Chick Contest.  I immediately jumped at the chance since I’ve been a fan of Howard since I was 12 years old!  So a few days later I ended up going on the show and it was a huge success.   

After the show was done taping and all the other girls were packing up their things to go home, I was approached by Doug Goodstein - the Executive producer of Howard TV, who asked me if I would be interested in being Miss Howard TV!  Of course I accepted the offer and a few days later I met with the rest of the Howard TV team to go over the details. 

When I arrived at the Sirius Office I didn’t even know what I was getting myself into.  I was nervous, anxious, but mostly excited.  I wasn’t even in the green room for 10 minutes and they were calling me into the studio to talk to Howard on the air.  I couldn’t wait to get in there but when I actually did I was really nervous.  Once Howard and the rest of the crew started complementing me, it put me at ease and I was a little more relaxed. 

Howard and the rest of the gang were still stuck on the fact that I was Tommy Hilfiger’s niece but then finally got over it and started drilling me about my boyfriend.  After answering around 50 questions about our relationship, Howard approved and said my guy was “a manly man.”  Howard said that he was happy that I was happy but I think Artie was still a little upset I wasn’t single. 

Once Howard found out that I didn’t have a specific outfit chosen for the taping he asked me to try on the sexiest one I brought.  Of course I tried on this pretty pink satin corset with black ribbons and a matching black lace skirt.  Howard said “it was hotter than any bikini” and my decision was made. 

I had some time to kill before we started taping so I went back in the green room to chill out and read over my script.  When I was in there I got a visit from my good friend Benjy which was really nice because I hadn’t seen him since the contest.  We were taping a segment together so we were both really excited about that.  After Benjy left I got a phone call from one of my best friends and sorority sister Danielle.  She was just calling to wish me good luck and find out what I was wearing!  It was great talking to her and very relaxing before we started taping. 

Before I knew it Isaac Mark, the senior producer (who’s also the coolest guy in the world) came in and said they were ready for me.  He took me back on set and we were ready to roll.  The first segment we taped was the one with Benjy.  It was so much fun and I got to find out some of my friend’s amazing talents.  It’s definitely cute when he flexes his calves and wiggles his ears!  Isaac said he was really impressed by how smoothly everything was going and how we were making really good time.  I did have a little problem after each segment I kept looking at Isaac’s cute face instead of looking at the camera like I was supposed to…oopps 

We took a quick break for lunch and shortly after we were ready to start taping again.  Everything went by really fast and before I knew it we were done.  After the taping we did a photo shoot of me doing various things around the set.  I’m so thankful that I was able to have this experience and I hope I could do many more things for Howard TV in the future.  Well, I hope you all enjoy the month of August!  I know I will because August is my birthday month!   

XOXO, 

Jaimie Hilfiger