As a new feature, I’m reliving the stories of my top 5 worst/funniest/best-date-story stories. Here’s the absolute worst date I have ever been on and is simultaneously the best story to tell…drumroll please…#1: Jessie’s Girl!!

Setting: Jalapeno’s Restaurant, Peru, IL, 2008

As many of you can imagine and some of you can attest to, the dating scene in Ottawa is not exactly jumpin’ jumpin’. Unbeknownst to many of you previous to my #5 worst date, I dabbled in the online dating world while living in O-Town, a few weeks on OKCupid, a few on Match. Not much came of the then-modern technology except for a few awkward dates that I immediately wanted to leave right after arriving and a few really great first date stories; in fact, my first ever worst first date story brewed from this initial experiment in online dating. I’d like to divulge said story not only to incite laughter, but to relive the glory days of grand ol’ Ottawa.

Continue reading #1: Jessie’s Girl →

As a new feature, I’m reliving the stories of my top 5 worst/funniest/best-date-story stories. Here’s #2:

In Hong Kong, I mostly had great first dates…except for Ear Licker. Here’s what I wrote in May 2011 about this wild date:

“I recently went on a first date with a random guy that I had met out one night. The night I met Pierre (names have been changed to protect the guilty), I was with Shelley in LKF, trying out new bars in town. Pierre asked Shelley if he could have my phone number and Shelley, being the good friend that she is, interrogated him about his personal life before giving the go-ahead: Are you married? Do you have a girlfriend? Do you have children? (actually, that was me chiming in in the background) Will you actually call her? He answered appropriately for each question, so my number was given, but with low expectation and even lower hopes that he’d call.

Continue reading #2: Ear Licker →

As a new feature, I’m reliving the stories of my top 5 worst/funniest/best-date-story stories. Here’s #3:

Exactly two years ago, I was taking my first foray into the rabbit hole that is Tinder. One mutual “love” was a 26 year old Puerto Rican military guy. We chatted on the app, exchanged phone numbers after an appropriate amount of commonalities, proceeded to text, then talk on the phone. We agreed to meet over drinks after work.

Right off the bat, in rapid-style, he gave me a 15-question inquisition about my job, my family, my hobbies. Tired from all the answering, lightning fire, I threw the question: What do you do for a living? at him. After a few moments of silence, he answered that he’s trying to think of a way to not scare me. Mafia? Mob? Hit man? I guessed.

I probed a bit further, “Can you tell me in like a summary? Just a few words?”

“I’m thinking!” he screeched.

Continue reading #3: The Yeller →

As a new feature, I’m reliving the stories of my top 5 worst/funniest/best-date-story stories. Here’s #4:

It was a sunny and beautiful day in Chicago just a few short weeks ago. I had forsaken online dating months previous and was letting the dating gods take me where they wished. During my lunch break, I was taking a stroll in the loop getting a few errands checked off my list and up in front of me walked a beautiful, tall man. I decided to let my I’m-so-goddamn-single-auras flow while I quickened my pace to get in front of him and his two friends. As I passed the beautiful man, I heard, “Can you tell me where Jimmy John’s is?” in a vaguely familiar foreign accent.

Oh my. It couldn’t be Mr. Handsome, could it?! As I looked over, his friend was talking to me. Apparently my auras were working, but with the wrong man. I decided to run with it anyway. He was foreign, so I should help them, right?! The group must be visiting from another country and have no phone data, it’s the least I can do to help out Handsome and his friends find a delicious, fresh lunch. It turns out Handsome’s friend lived and worked in Chicago, and hailed from Turkey originally.

After I directed the trio to the nearest JJ’s, Señor Questions (not the cutie, mind you) started chatting me up: where do you work, why are you so gorgeous (juuuuuusst kidding…), and would I like to get coffee with him sometime. My goodness was my aura in sync that day! I agreed, thinking what’s the worst that could happen? And when we did get drinks, nothing bad did happen! It was rather nice actually. He even walked me to my office and right on the spot asked me to hang out again. Who doesn’t love a man with cajones, amiright, ladies??

The next night, we met for drinks of the alcoholic variety. BUT the entire vibe had changed. He had turned the creep factor up to 10. He asked to meet my parents. He requested that I take him to visit N.I.U. since that’s where he got his masters and because my parents live so close. He insisted that we were a match made in heaven because we lived in three of the same cities. At one point, he grabbed my hand in order to “help me cross the street like a gentleman.” I yelped that I was quite capable of walking with my own two feet and my own two hands, thank-you-very-much.

Continue reading #4: Mr. Let’s Get Married…Tomorrow →

As a new feature, I’m reliving the stories of my top 5 worst/funniest/best-date-story stories. Here’s #5:

Approximately 7 years ago, I had my first bout of online dating. This was when going online to find a date was a combination of secrecy, exhilaration, and creepiness. I met exactly 4 guys in the 4 months I drank the match.com Kool-Aid. This is a story about one of the few men that actually went online looking for a date in LaSalle County.

Steve was a nice enough fellow. We met for ice cream on our first date and decided that it was “good enough” for a follow-up meeting. The new Batman movie was coming out and, while going to the movies is a terrible second date idea, Batman is my favorite superhero.

Going to the movies on a date is strange since there’s no time to talk and get to know one another…unless you’re Steve. Steve decided to talk the entire time the previews were playing and play a little game I like to call “get to know my fresh and new date with 20 questions while the previews are playing in a very full theater of people.” This included such gems as what’s your favorite flavor of ice cream, why did you travel to China in college, and do you have any siblings. If you’ve ever seen a movie with me, you know that I hate to be late to movies because I LOVE the previews. They are like their own little movies and the only words I want to say/hear during this 20-minute prelude is: “That looks terrible” and “I can’t wait to see that!”

Continue reading #5: Batman →