February 13th, 2010 by The Barefoot Blogger: Laura Kleinbaum

Valentine’s Day is on its way and there are countess ways to spend it.  We all know what that means: countless shoe possibilities.  Whether you’re in a 20-year marriage, single in the city, or something else in between, there’s a way to celebrate and corresponding footwear.  A disclaimer: by celebrate I mean acknowledge the “holiday” at all.  We all know it’s sort of made up and definitely hyped up.  But hey, one thing’s for sure-it’s gotta be more fun than New Years.

The ‘Putting some spice back into the relationship’ Romantic Evening: As per your subtle hints over the past month and a half, your significant other of who-knows-how-long-it’s-been has booked a couple’s massage and the presidential suite.  Room service and matching white robes are going to be involved.  He might have also hidden a little blue box in his overnight bag, so you’re probably going to want to put out.

The Single Girls’ ‘Burn Your Ex’s Stuff’ Party: After getting together for brunch and subsequently going to see Valentine’s Day, (Who am I kidding?  Everybody’s seeing that.) you and your girls will gather at someone’s apartment, ex’s stuff in hand, and  fueled by heartache, rage, and white wine, you’ll climb out onto the fire escape and burn a bunch of boxers, teddy bears, and probably a retainer.  By the time the firemen and your very angry super have left, you’ll feel ready for dancing.  Dress for that.   You’ll be making out with someone else’s ex in a dark club in no time.

The ‘I can’t believe he asked me out on Valentine’s Day’ Date: This is new, real new.  You’ve hung out a couple times and now he’s asked you out on this day of all days?  You may very well be too distracted analyzing his every move, word, and past text to enjoy your pre-fixe meal and the second least expensive wine on the list.  So at least feel confident in your shoes, beautiful but not too dressy.  And then come on, he did ask you out on V-Day after all.  He’s into you-enjoy it.

Hint: Don’t stress if you can’t return the sentiment.  There will plenty of time for meeting your single friends for dancing later.  They’re already wasted and smell like fire-they’ll be out all night.

The ‘Creative Boyfriend’ Date: He planned a surprise and you can bet it’s not just going to a restaurant.  Wear comfortable but very attractive flats, the kind that can transition from day to night.  Just remember to try and take a break from staring into each other’s eyes and petting long enough to enjoy the activity.  God, you’re so cute it’s making everyone else gag. Who even cares what you wear?!

The Shoes:  The All Black for BFT Crosstoe II, The Madden Girl Century, The All Black for BFT Quilted Flat, The Delman Anouk (All available at Barefoot Tess)