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
No Strings Attached
The first time I’ve ever had a consistent hookup where I had virtually zero emotions invested.
Hang Outs, Kinda Catfish
Bumble, Booze, & Breakups
Two guys, five dates, and a whole lot of alcohol.
Juan Pablo Syndrome
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.
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.
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)
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
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.
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
Delayed Update on My happn Dating Spree
Five months delayed, but better late than never.
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?”
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’s Doppelgänger
A typical asexual dating tale from the Picky Dater.
Picky Dater Meets Picky Eater
And I thought I used to be a picky eater.
Kinda Catfish, Food Compatibility, Dull
The Moccasin-Wearing Admirer of Sidewalks
This hipster thoroughly enjoyed what most people don’t notice. And moccasins.
WTF Are You Wearing, Just Strange
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
Serial Dating in Cuffing Season
Lots of dates in a short amount of time
Doctors & 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
…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
Recycling 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
Don’t Settle for Less Than You Need
How to evaluate what you want and need and how to go about getting it
From Dating to Hooking Up & Everything In Between
The background story of the hookup guy that eventually came back in my life two years later
My First Awkward First Date
The med student that I just didn’t have much in common with
The Land Down Under
The Australian that made me stop being attracted to Australian accents
TMI, Bad Kisser, Bedroom Embarrassment
Booze Bag Criterion
The guy who sounded like Sean Connery and didn’t drink
Sex 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
How to Do Everything Wrong & Get a Second Date (Pizza)
Aftermath of the first date with the pompous douchebag
No Basic Manners
The Attractive Pompous Douchebag
One of my favorite bad date stories (part 1)
Inconvenience, Kinda Catfish, Pompous, First Date Check
It’s Not You… It’s Me
The hilarious guy that I wish was my best friend
The Steve Urkel-sounding guy who asked to give me a bad kiss
Work Obsessed, Bad Kisser
Dating Déjà Vu
The guy who saw me on a date with someone else last week
Kinda Catfish, Juan Pablo Syndrome, Chronic Swearer
Overbooked 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
So Much for My New Year’s Resolution
The guy who tried to convince me to be Atheist
TMI, Debate Team Champion
Getting Back on the Hinge Horse
The guy with the most confusing body language ever
Juan Pablo Syndrome, Work Obsessed, Bad Body Language
That Time I Was a Contestant on The Bachelor
The first guy I really liked via online dating
What a Good Kiss Can’t Do
At least the guy I asked out was a good kisser
The 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
One Drink Wonder
The swearing, judgmental, self-centered guy
Chronic Swearer, Juan Pablo Syndrome, Judge Judy
Anesthesiologist: 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
Final Attempt at Tinder Dating
The over-sharing Stage-5 Clinger fresh out of a bad breakup
TMI, Juan Pablo Syndrome, Stage 5 Clinger
Expanding 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