Slash Coleman M.A.Ed.

Slash Coleman M.A.Ed.

Bohemian Love Diaries

Five Awkward First Dates You Probably Want to Avoid

Front Line Dating Tips: Awkward to Amazing in 5 Easy Steps

Posted Aug 09, 2013

Five months ago, at the height of my New York City dating orbit, I found myself locked in the equivalent of the Star Wars cantina closet. I couldn’t get out. I checked the door. It wouldn't open. Deciding my relationship rocket was in need of repair, I decided to take it into the shop and go on a dating hiatus.  

"What is pride? A rocket that emulates the stars." - William Wordsworth

I chose five months because that’s when my book, “The Bohemian Love Dairies” (my memoir of failed love relationships) would be published. I saw the publication date as a symbol notched into my love karma. From that point forward, I’d be able to not only start a new chapter but I’d be able to start a new chapter in a new book, one in which I’d no longer be my own worst enemy who, like a bossy pants older sister, kept locking me in the Star Wars cantina closet.  

In my quest to start afresh, I began to scour the interwebs for dating advice. 

Imagine my utter delight when I met Amy Neswald on Twitter (@50_dates) - a self-proclaimed experienced adventure-dater and exquisite wordsmith. She’s not only been on over fifty dates in 17 of the United States (with a 95% success rate at securing an offer for a second date), but she’s on her own dating quest - in the process of going on fifty dates in fifty states which is the equivalent of writing "Eat, Pray, Love" without the eating, praying, loving....or a pen. (>check her adventure out here)

A good example of 10 awkward first dates. If the cars contained married couples, they would've been hidden in the gulch.

As I prepare my rocket ship for take off this week, I plan to tape her guest post on the instrument panel console right above the fuel gauge. It’s good. It’s written in a language I can understand. And so, I hope you’ll tape it above your fuel gauge as well. 

1. The Mutter Museum, Philadelphia, or any museum of medical oddities.

It’s enticing. A museum that houses the corpse of a woman who turned into soap, busts of conjoined twins, and slices of Albert Einstein’s brain. It seems like the perfect place to meet a promising stranger for the first time. And when you walk through the regal, Ivy League doors of one

To the untrained eye this is a vintage oddity. To an eccentric Bohemian like me, photos like this really get my heart racing.

A better alternative: Stew Leonard’s, where you can watch machines pour milk into cartons while a giant animated celery sings about being a piece of produce. Later, you can hold hands with your date while petting an anemic-looking goat in the petting zoo. 

2. Any Dog Park, Anywhere, USA

You both have dogs. And that’s a good sign because you’ll both have something to talk about even though you have nothing in common. But moving too fast on a dog date can be detrimental to a potential love-match.

Things are terrific when you meet Mr. Might-Be-Right and his five year-old, high energy, husky mix. They’re like the rugged, wild-west version of you and your little doe eyed Pomeranian, Precious, who fits in your purse.

At the dog park, alone in front of the tv, at your wedding... it's always a different story when it comes to dogs.

A better alternative: pet puppies at a puppy store.

3. A Theatrical Performance You Know Nothing About

You’re multi-tasking. You’ve scheduled a date the night before you have a theatrical magazine review due. It’s an off-off Broadway play you know nothing about, but you have an extra ticket. Prior to the show, you and that long, tall, sensitive drink of water share a promising glass of wine and some light conversation, but since your recent break-up and his life-altering surgery, you don’t want to give away too much, or let things to move too fast.

Sitting in a dark black box where you don’t have to talk, can’t come soon enough...

Cue the man with the beard. The audience will watch the man watching the audience watch the man.

A better alternative: a park with a movie night. There’s free entertainment and you don’t have to talk. Plus, you can set up your own two-for-one drink special with a thermos or two...or three.

4. Any Physical Activity That Involves Balls, Yoga, or Water

He’s a guy who never was into sports. He’s been beaned in the head by far too many whiffle balls to consider playing with balls ‘fun.’ You discover this when you find him crying behind the bleachers at the competitive dodge ball meet-up you invited him to. You’re out of Kleenex and offer him your sleeve. Oh, well.

“I’m in good shape. That shape is round.
” ― Jarod Kintz

Still, you persevere. Neither you nor your next date have been stand-up paddling, but it sounds fun! Until you realize, just a little too late, that the only bathing suit you own has a padded bra and a skirted bottom. To top it off, your legs are pasty white and you forgot to shave. You’re balancing on a surf-board in the middle of the Hudson, where it's been rumored that the water will eat your skin, praying that you don’t fall in... It doesn’t matter who suggested this. Someone asked and someone else said yes.

Also off the list: competitive IQ tests, trivia, and scrabble. You never know when a competitive sport will release your date’s deep-seated traumatic childhood memories.

A better alternative: play a game of chance. Like bingo. Or spin-the-bottle.

5. Any Dunkin’ Donuts or Starbucks Kiosk Located Inside a Mall

I make it a rule not to date at chain restaurants, but one of my first dates met one of his first dates at a Dunkin’ Donuts at a Wal-Mart in Vermont.  Here’s what happened:

“I should’ve known. She was twenty years older than the picture she had online, and fifty pounds heavier. But that didn’t matter. It was when she started talking about how she loved being pulled into the fourth dimension but could never remember where the portal was that threw me. You can tell a lot about a person by where they choose to meet.”

Did you get the memo. Everything in the 4th dimension is Hello Kitty.

What did he and I do on our first date? We searched for a defunct auto-repair shop deep in the bowels of Chinatown.

A better alternative: almost anything. Except the Mutter Museum.


Join guest blogger Amy Neswald (a New York based writer, filmmaker and blogger at "50 Dates in 50 States" which chronicles her attempts to date across the country while holding down a full-time job) at, @50_date or

Join Slash Coleman, the author of this blog, on all of his mischievous adventures at Twitter:Slashcoleman - Facebook: slashtiphercoleman - Pinterest: slashcoleman - Website: - Instagram: fishoranges