Jen Winklepleck

Bartender, Karaoke Diva, Reality TV Star and fearless Adventuress

"Try everything once, and sometimes twice... die broke and full of experiences, and make sure to bring as many people on your journey with you!!"



    1. What is the most adventurous thing you’ve ever done?

    The most adventurous thing I've ever done would have to be when I moved to Vail, CO. I packed a couple suitcases, my snowboard, and the drive and ambition to do something daring. I didn't know a single person when I went out there. By the time I left, I knew practically the whole town, and I got to experience new things I would never have tried otherwise (snow shoeing, moon light snowboarding, riding ski bikes, late night hikes thru colorado, hot springs in the winter...) The entire experience was truly life changing. I met a gaggle of friends from other countries, which sparked my desire to become well travelled (have now been to over a dozen different countries and don't plan on stopping any time soon). Oohh!  I finally tried surfing!  That's adventurous and exciting!


    1.  Is it an adventure being a female bartender? Why?

    It is ABSOLUTELY an adventure being a bartender!  I get to meet so many different people and so many different kinds of people. The more people you meet, the more potential there is to be exposed to something new and different. I've had many friendships flourish and develop because of bartending. In fact, I'm in Hawaii this very moment because of bartending. The greatest part: super flexible schedule which leaves me lots of room to go out and enjoy the things I love doing. 


    1. What makes a good bartender?

    A good bartender is more than just knowing how to make drinks. In fact, that's the part that CAN be taught. You can't teach "personality" or the ability to read people. One thing people don't understand about bartenders:  we're there as an outlet for so many kinds of people. Someone breaks up with their significant other, well, I've got a drink for that and a pair of great ears to listen to their story. First date?  I'll help ya with breaking the ice and loosening up a little. So I'm in charge of being a different role for handfuls of people...usually all simultaneously. Not only that, in Oregon, we have incredibly strict liquor laws...so I'm responsible for my customers when they get hammered. As bartender you're doing a million things at once (making drinks, chatting with new people, listening to someone about how their dog pooped in their shoe, making sure drunk Tommy is safe enough to get home, taking in deliveries from purveyors, making sure that obnoxious guy stops bothering the poor gal that just wants to finish some leftover work stuff...) Just a random example of what could be going on for me at any given moment. So cut your bartender some slack when you walk in on a Friday night while we're arms full and four rows of people deep at the bar...yelling at me because I couldn't get you your Jäger bomb INSTANTLY isn't going to make your drink appear any faster...


    1. Would you recommend it to other adventurous women?

    I love bartending, but it is definitely NOT for just anyone...


    1. Do you really get to hear a lot of fun “stories?” Is being a bartender mean also mean being part psychologist?

    I hear some crazy stuff when I'm bartending.  I have my own, unspoken, bartender/customer confidentiality agreement...I'm not gonna run off and tell other people your private stuff...but then again, I'm a rare bartender.  Now...I've SEEN some crazy stuff, too....there's enough of that to fill an entire book.  People are funny when they're drunk.  You get to see a side of them that not many people get to see.

    6.  Best tippers: men or women?

    Neither men nor women tip best.  I treat everyone the same, no matter what you look

    like.  If I'm doing my job properly, they tips will show.  If not, that shows, too...I'm in

    direct control of my income, but I don't look at it as a per scenario thing...plus, the

    money flow changes through the year, so I try not to get hooked up in it.   Like I said, if

    I'm doing my job correctly, the $$ will be there.

    7.  What is your favorite holiday drink and how do you make it?

    My favorite holiday drink to make is an eggnog that I won the People's Choice award for during the Northwest Annual Eggnog competition.  It's called "Wakey, Wakey, Eggs and Bakey."  The eggnog itself was prepared in a tradition eggnog style, using both Zaya (aged dark rum) and Captain Morgan (spiced rum), pure and true maple syrup, and the kicker was the bacon flavored whipped cream to top it all off.  It was like having french toast breakfast in a cup...adult style.  Soooo delicious...slightly time consuming, so not the "friendliest" of at-home cocktails.  A good and simple holiday beverage is called a Peppermint Patty.  Simply take your favorite peppermint schnapps (i love Rumpleminz) and add it to some hot cocoa.  Crumble a few candy canes over the top and you have a quick, easy, and festive looking holiday cocktail!!

    8.  You do karaoke at your bar, too. Where do you find the courage to get on stage?

    We don't actually have "karaoke" at my bar.  We have a live dueling piano show that I

    get to be a part of!  It's a legit band...pianos, guitars, drums...we have regular band

    rehearsals and everything.  Karaoke is walking into a bar, picking a song out of a book,

    and reading the usually incorrect lyrics off a screen...  I sporadically jump on top of my

    bar and sing random top hits as needed.  Myself and one other bartender are they only

    two that work and perform at the same time. 
    Finding the courage to get on stage is something that has taken me years to perfect.  I

    am STILL always watching other performers and trying to pick up new tricks to help

    enhance my own performance.  But it's all about hours on the stage...the more you do

    it, the more comfortable you eventually become.  It's still nerve wracking every

    time...but that's also half the fun.  :o)  I also am in a couple other bands.  One of them I

    actually play guitar in.  :o)

    9.  What is your funniest karaoke moment?

    My funniest karaoke moment??  There have been many....I've done an amazing

    rendition of Lionel Richie's "Hello" but in my silly asian voice and sang it "Herro."  There

    was auto tune involved as well.  It was comical.  My funniest moment on stage in

    general?  There was a time I was watching a friend's band play...I had been drinking a

    little and I was called onto stage to perform a song with everyone.  I maybe had a couple

    drinks too many, but let's just say I do an AMAZING Eminem...you just had to be there. 

    Everyone that was, still mocks me to this day.

    10.  We love your bungee jumping video in a skirt! Was it as terrifying as it looks?

    Bungee jumping is BY FAR the scariest thing I've ever done in my entire life.  Somehow I managed to do it FOUR TIMES!!  I have no idea what I was thinking, but I'm pretty sure I'm good in the bungee department for a long time.  I'm deathly afraid of heights...I try to not let it rule my world, but it made that experience THAT MUCH more scary...I am DEFINITELY and GENUINELY scared out of my mind in that video...skydiving on the other hand...THAT'S a fun adventure!!

    11. What are you afraid to do?

    I'm afraid to fall in love.  It's scary and you're always vulnerable!  It's an amazing feeling

    when you find it, but it's scary...

    12.  Where you an adventurous girl? How did you become so fearless?

    I was not an adventurous girl growing up.  My mother was extremely strict with us.  We weren't allowed to leave the house, even to play with neighbor kids.  As soon as I was old enough to be on my own, my world was opened up to all of these endless possibilities.  I am as crazy and extreme as I am cuz I've got some makin' up to do!!  All those years stuck indoors??  Never again!  :o)

    13.  Who is your heroine?

    1. I can't say I have one single heroine.  I admire so many women.  Snowboarding:  Gretchen Bleiler KILLS it...and she's incredibly INCREDIBLY beautiful...I wanna be her.  :o)  Musically, there are so many amazing women out there...cheesy as it is, Sara Bareilles is who I've been admiring lately.  Look up her version of "Sittin' On The Dock of The Bay"...it's beautiful.  All of the girls I met on Wanted II (Reality TV Show) are all admirable women that anyone could look up to!  I have a huge appreciation for any strong woman that can think for herself and tries to go out and dominate life!  We're not on this planet for a very long time...why just sit and watch the world pass you by when you be out there filling your time with experiences???  Get out and try something new!!

      14.  What was the best advice your Mom ever gave you?

    The one piece of advice my mom gave me was just to never give up.  I know that

    everyone's parents say that to you, but whether you truly do it is the difference.  I have

    some of the most amazing and talented friends in the world...I see them struggle

    regularly, but they when they have that "it" moment, all of the hard work and struggle

    has paid off.  I want to influence people in the world in the way that my friends have

    influenced me.  I'm jealous of some of their successes, but only because I want that

    same thing.  That jealousy inspires me tremendously!  Hard work pays off...it's that

    simple.  There's no special formula...no man behind the curtain...you get results

    comparable to the work and effort you put into what you do.

    15.  What adventurous thing is on your Bucket List for 2012?

    The most adventurous this on my 2012 bucket list??  Hmmm....I'm gonna self-publish my book.  That's scary and adventurous!!  Also, I just bought a ukulele...I'm gonna start playing it on stage!!  I'm excited!!

    16.  What is your life motto?

    My life's motto is, "Try everything once, and sometimes twice...die broke and full of experiences, and make sure to bring as many people on your journey with you!!"

    My website: (though not entirely complete) http://www.jensaysdotcom.ne; My blog is there, with my bungee video and some other random stuff.