If there was a problem, yo Will solve it.

William Elliott Whitmore is an American treasure, and he’s here to answer your questions and life problems.  Check out Will’s advice to three Postcard Elba readers below.

Dear William,

This isn’t so much a personal problem that I need fixed as it is a regular question for you.  Hope that’s ok.

I was playing Red Dead Redemption and heard a song by you on the soundtrack.  Made me wonder – what’s your favorite western movie?  And if I can ask a second question – what’s your favorite video game?

Big Gamer

Dear Big Gamer,
There’s dozens of great films of the Western genre that I appreciate,  but one of my favorites has always been  “The Outlaw”.   It was made back in the 1940’s by none other than Howard Hughes.  Check out Jane Russell’s “acting talent”.    I don’t really know much about video games,  but I’ve always thought there should be a “Banjo Hero”.


Hey Will!

There’s a girl who lives across the street from me that I want to ask out.  We’ve never even talked before, just sort of nodded heads at one another whenever we’re both outside at the same time.  I don’t even know her name.  What’s the best way to approach her and ask her out?

Coveting My Neighbor

Dear Coveting My Neighbor,
The fact that you’ve seen each other numerous times outside is good.   I’ve always thought the direct approach to be best.  Next time you see her outside,  go and talk to her.  Ask her name.  Keep it light and make the first meeting short and non-creepy.  Try to end the encounter on a high note.   This will make you both happy and your hearts will sing as you go through the rest of your day.   Do this with increasing regularity and duration until it feels right to ask something like,  “Hey, one of my favorite bands is playing tonight,  you want to go have a drink and hear some music?  It might be fun and lord knows we could use some distraction from this oil spill nonsense.”    If she says no,  accept it graciously and start leaving weird stuff on her doorstep.  If she has a boyfriend,  you’ll have to settle for admiring her from afar with quiet longing.

Dear William Elliott Whitmore,

I am a young person out of college faced with a Career Problem. On the one hand, I have a pretty good job as a secretarial type that I am completely bored with, but some new freelance work is helping that a bit. On the other hand, I am faced with the possibility of taking on a new job, but it presents its own challenges. Basically, I’d be working with autistic students to help them manage various tasks. I am sure this would not be boring, but I am afraid that it might also not be something I can handle. So do I stay put where I know things are alright, hoping to gradually decrease my secretarial hours and take on more freelance work, or do I try out this new job and hope that I can handle it?

—Should I Stay Or Should I Go?

Dear Should I stay or should I Go,
Career choices are never easy.  The advantages you have at the moment are your youth and vigor.    Although it will be challenging,  the option of helping autistic students sounds like an adventure.  Just think,  you could make a real tangible difference in someone’s life and meanwhile feel a sense of reward that not many people get to feel.  Everyone that I know who has a similar job loves it.   Give it a try at least,  let it enlarge your soul.

Need Will’s help sorting out your life?  Send your question to postcardeditor@gmail.com with WWWEWD? in the subject line.

William Elliott Whitmore is “America’s greatest living songwriter” according to the Pogues’ own Spider Stacey.  His latest album “Animals in the Dark” is available from Anti-Records.

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