Valentine's Day Advice from Jay Cutler

We know that Jay Cutler is a hopeless romantic, as evidenced by his marriage proposal via text and mailing of the ring to fiance Kristin Cavallari.  So we’ve decided to do a simulated dating advice column with the Bears quarterback.  Let’s call the segment

Scoring… with Jay Cutler

Dear Jay,

With Valentine’s Day coming up, what do you suggest is the perfect night out to let a girl know that I really like her?  What can I do to impress her on a first date?

Thanks and Bear Down!

Johnny from Melrose Park


Thanks for writing.  I know it’s tough to sometimes show that special girl how you really feel.  Don’t worry, I’ve got you covered.  First of all, send that special girl a tweet to ask her out.  You don’t want to come off as desperate plus you don’t want to waste time yapping on the phone with her, so a quick tweet should get the message across without coming off as needy or clingy.

Next, make sure you get yourself together.  Make sure your ‘Soldier Field’ is properly ‘landscaped’ if you know what I mean.  You don’t want to be in the victory formation later in the night and have a poor playing surface.  Throw on a pair of jeans and a button down or if you really want to impress her, get yourself a sweet pair of salmon colored pants.  Chicks dig dudes that aren’t afraid to wear pink pants.

A lot of guys might make the mistake of trying to pick some fancy steakhouse for a first date.  DON’T DO IT.  You can’t set the bar too high too early.   Take her to Portillo’s drive-thru but be classy and order for her.  Chicks like a guy who takes charge like that.  Order her a Chicago style hot dog – no ketchup of course – and if she gripes about it, she might not be the right girl for you.  Make sure you order with no onions ’cause you don’t want to taste that crap when you’re sucking face later in the night.  Watch how she handles the dog and if she’s squeamish, she could be riding the bench before the night is over.

A lot of guys will try to take the girl to see a movie at the theater.  That’s another big mistake that you should avoid.  How are you supposed to make your move in a crowed theater?  Instead, take her back to your place for a movie on the couch.  If you’re like me, your bachelor pad is fully equipped to handle this.  Don’t do some cheesy rom com, instead, watch a good action movie to help get your juices flowing.

By the time the movie is over, you should be ready to close the deal.  If she’s not ready to go no-huddle, it might be time to call an audible and call one of your backup groupies up before it’s too late, but assuming the girl you invited out is ready to roll, make sure you’re hitting the gridiron with your helmet on.  Protect your blindside better than J’Webb protects mine or you could end up stuck with a little rug rat and washed up reality star keeping you from hitting the free agent market.  Most importantly, if things go south, don’t be afraid to scramble.

Hit me up for more advice so I can help you score in love and in life.

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