Dating Chronicles

While I may not live the most out-of-this-world interesting life, I do have to say that my dating life is pretty amusing.  Being single (and picky) for over four years now, I’ve had more than my share of unsuccessful, hilarious, and bizarre dates.  Below I’ve listed and summarized them by publication date, so have at it.  Oh, and since I’m judging all these guys, feel free to judge me back and leave comments, ask questions, give suggestions, whatevs.


Ten Inches of Disappointment

If you are going to talk the talk, then you better bet that I am going to make you walk the walk.
Bedroom Embarrassment, Stage 5 Clinger 

that's right

No Strings Attached

The first time I’ve ever had a consistent hookup where I had virtually zero emotions invested.
Hang Outs, Kinda Catfish

immediately regret

Bumble, Booze, & Breakups

Two guys, five dates, and a whole lot of alcohol.
Juan Pablo Syndrome

it's a miracle

50 Shades of Chris

Guys named Chris may be the cure to my pickiness… if only my experiences with them would actually work out for once.
Girl-ish Tendencies

not again

The Aussie Who Was Headed Back Down Under

Not much to say other than he wasn’t going to be here much longer… and he is the reason I have any recent bad karma.

i'm a grown woman

Because I’m a Grown-Ass Woman, That’s Why

Tequila and Uber were all I needed to make use of those expiring condoms next to my bed. (Part 2 of 2)

im right youre wrong

This Year’s Version of the Attractive Pompous Douchebag

If you aren’t familiar with the original Attractive Pompous Douchebag, then scroll down and read about my dates with him first.  It’s unfortunate how similar they are.  (Part 1 of 2)
Juan Pablo Syndrome, Pompous, Judge Judy

you are welcome

The Virgin to Online Dating (& How I Set the Bar Way Too High)

Making first date dreams come true, one online dating newbie at a time.

wtf bro

Moving & Grinding Never Go Well Together

If you are permanently leaving the state and put your crotch on girls when you dance, then things will not work out well between us.
Inconvenience, Work Obsessed

you shall not pass

Delayed Update on My happn Dating Spree

Five months delayed, but better late than never.

may the odds be ever in your favor

New Year, New Apps, New Date, New Letdowns

If you don’t like guac, you’re automatically out.
Inconvenience, Just Strange


OKCupid Asks, “Would You Dump Someone Simply Because They Weren’t Good at Sex?”


watch law and order

More Mediocre Back-to-Back Dates

At least I got a free comedy show out of it.
Dull, Bad Body Language, Male-on-Male Tendencies, Judge Judy

adrian grenier lookalike

Adrian Grenier’s Doppelgänger

A typical asexual dating tale from the Picky Dater.

too hot foodPicky Dater Meets Picky Eater

And I thought I used to be a picky eater.
Kinda Catfish, Food Compatibility, Dull

stacy clinton shockingThe Moccasin-Wearing Admirer of Sidewalks

This hipster thoroughly enjoyed what most people don’t notice. And moccasins.
WTF Are You Wearing, Just Strange

dont go

The Movie-Referencing, Touchy-Feely Subway Kissing Stalker

This guy just really liked movies and kissing girls in subways
Pompous, First Date Check, Bad Kisser

evil laugh

Serial Dating in Cuffing Season

Lots of dates in a short amount of time

staring squintingDoctors & Kissing (A Public Service Announcement)

We need to raise awareness about the fact that too many doctors can’t kiss
Kinda Catfish, Speak Up!, Bad Kisser

this is happening…Until You Realize You Have the Same Tainted Goods You Discarded in the First Place

Here’s what happens when he doesn’t tell you he is IN the wedding he invited you to and nobody knows who you are. Parents included.
Inconvenience, The Total Stranger, Fade Away

you change your mindRecycling Seems Like a Great Idea at First…

Recycling for sex? All fine and good.  Recycling for relationships? Not so much.
Hang Outs, First Date Check, Hot and Cold

aint nobody got time for thatDon’t Settle for Less Than You Need

How to evaluate what you want and need and how to go about getting it

ignore youFrom Dating to Hooking Up & Everything In Between

The background story of the hookup guy that eventually came back in my life two years later

thumbs upMy First Awkward First Date

The med student that I just didn’t have much in common with

screaming yesThe Land Down Under

The Australian that made me stop being attracted to Australian accents
TMI, Bad Kisser, Bedroom Embarrassment

cheers to wineBooze Bag Criterion

The guy who sounded like Sean Connery and didn’t drink

cher trying for attentionSex at Dawn without a Kiss

Only thing worse than the first date with the pompous douchebag was the second date
Debate Team Champion, Judge Judy, Bad Body Language

rudeHow to Do Everything Wrong & Get a Second Date (Pizza)

Aftermath of the first date with the pompous douchebag
No Basic Manners

reallyThe Attractive Pompous Douchebag

One of my favorite bad date stories (part 1)
Inconvenience, Kinda Catfish, Pompous, First Date Check

want it nowIt’s Not You… It’s Me

The hilarious guy that I wish was my best friend

there is no one that can do what i doImpromptu Letdown

The Steve Urkel-sounding guy who asked to give me a bad kiss
Work Obsessed, Bad Kisser

catfishDating Déjà Vu

The guy who saw me on a date with someone else last week
Kinda Catfish, Juan Pablo Syndrome, Chronic Swearer

you are really seriousOverbooked and Caught Red-Handed with OKCupid

When next week’s date saw me out with this week’s date
Juan Pablo Syndrome, Total Bro, Dull, Inconvenience, First Date Check

help me im poorSo Much for My New Year’s Resolution

The guy who tried to convince me to be Atheist
TMI, Debate Team Champion

sarcastic good jobGetting Back on the Hinge Horse

The guy with the most confusing body language ever
Juan Pablo Syndrome, Work Obsessed, Bad Body Language

best date everThat Time I Was a Contestant on The Bachelor

The first guy I really liked via online dating
Hang Outs

dull boredWhat a Good Kiss Can’t Do

At least the guy I asked out was a good kisser

total bro fist pumpThe Time I Picked Up a Guy at a Bar

The guy that was good looking enough from far away to make me ask him out via napkin at the bar
Total Bro

judge judyOne Drink Wonder

The swearing, judgmental, self-centered guy
Chronic Swearer, Juan Pablo Syndrome, Judge Judy

bad kisserAnesthesiologist: Round Two

The boring anesthesiologist bro who can’t kiss
Dull, Bad Kisser


The First Time That Coffee Met Bagel

The anesthesiologist bro
Total Bro, Juan Pablo Syndrome

sad hug

Final Attempt at Tinder Dating

The over-sharing Stage-5 Clinger fresh out of a bad breakup
TMI, Juan Pablo Syndrome, Stage 5 Clinger

throwing headsetExpanding My Horizons to the Online Dating World

He showed up with his stethoscope & couldn’t parallel park
Inconvenience, WTF Are You Wearing, Male-on-Male Tendencies

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