Rah-Rah-Ah-Ah-Aha…Roma, Roma-ma…GaGa, ooh-la-la! Just like GaGa, we wanted your bad romance and you gave it to us. We always knew dating can be scary - but your stories make that claim reach a whole other level. Thank you to everyone who sent in their stories we wish we could give everyone a prize to help heal your dating wounds, but there could only be 1 winner. “Advice From a Jerrk” columnist Jerrod chose his favorite bad romance story (Congratulations to Cara!), and the PLRG team chose some other quality stories to share with you. May they make your Valentine’s Day week seem a little bit brighter…
Winning Entry - “Mr. Most Wanted”
Last year on my birthday, my insane friends treated me to a night on the town. I couldn’t tell you where we went, all I know is that we ended the night at Barleycorn in Wrigley. I ended up meeting some guy and apparently gave him my number. I woke up the next morning on my couch in my dress from the night before with a million texts from this guy (should of been the first red flag). I couldn’t remember his name or what he looked like (the girls told me from what they remembered, he was a good looking guy). I agreed to go out with Mr. Barleycorn and gave him the head’s up that I was a strict vegetarian. A week later I met up with him for our date. He takes me to Shaw’s Crabhouse- where I think the only thing on the menu without meat is a side salad, orders a bottle of wine and begins to tell me about himself….here’s what I learned or what I remembered the most- he was 10 years older than me (really not that big of a deal) and still lived with mom and dad. Dinner continues and so does his drinking. I had a glass of wine and switched to water. He finished the wine and switched to dirty martinis (5 martinis). After dinner he asked if I wanted to head to a bar for another drink- at this point I should of said no, but I didn’t. We go to Harry Caray’s and I continue to drink water. He had 5 more mixed drinks. He started getting all touchy feely with me and when I asked him to stop he wouldn’t. I politely asked him to respect the fact that I said to stop and his reply was “You don’t think I respect women? The last time I had sex was 3 years ago.” At this point it was time to go home. We hop in a cab and he asked the driver to take him to his car so he could drive me home. I told him he would not be driving me anywhere (the cabbie also yelled at him for even thinking to drive at his level of intoxication). I had the cab driver drop me off at the corner, thanked him and started to get out. He then asks if he gets to come with me. I politely say no and he that really pissed hm off. At this point I just say sorry and leave. For the next hour I got texts from him that said things like “well I guess I will just sleep in my car,” “Thanks for nothing bitch,” etc. I ignore the texts and go to bed. Fast forward to Monday, just when we thought it couldn’t get any better, while bored at work I google search Mr. Barleycorn. His name pops up under “Indiana’s Most Wanted.” Intrigued, I click on the site. Up pops his mug shot. Luckily, he was only (I say this lightly) wanted for a re-arrest to failure to appear in court for too many DUI charges….imagine that. So that’s my horrible date. Great story to tell the grandkids.
-Cara
And the runner-ups…
So here I am excited to jump back into the world of dating after my relationship of six years falls apart, and I agree to be set up through a mutual friend to catch a movie with this guy. I’m dressed and ready to go when I get a text message from my date saying he’s running a few minutes late, but when I call him back to clarify how late he informs me that he hasn’t yet left his house (he lives almost an hour away). He suggests that I drive and meet him at the theatre, so I finish getting my things together when I get another text- this time, saying he’s pressed for cash and asking if I would cover him for the movie tonight. Let me be clear, I have no problem paying for a date, but he could not have made a worse first impression! Tardiness, frugality, and the general lack of courtesy to actually call with his little updates were too much for me to handle. This time it was my turn to text back and say something had come up. What a prince charming.
-Anna
My worst was many years back, like 20 year ago, I was 17 and working at the Walgreens on Lawrence and Pulaski in the city. It snowed really bad that day, I mean really bad. I was determined to see my boyfriend and bring him his card that I bought him. So I trudged, yes trudged through snow that was higher than my ankles from Lawrence and Pulaski to Montrose and Kimball. I walked all that way and when I got to his house I found him in nothing but biking shorts and wiping sweat of of his chest and the blonde friend from across the street. He told him they had just been working out. Yeah I bet!
-Candice
My dating disaster starts off as anything but. I met a nice looking gentleman the previous weekend at our local watering hotel. Handsome good looks? Check. Ability to carry on a conversation without putting me to sleep? Check. Left finger sans ring? Check. Lack of obnoxious, rude, drunk friends gallivanting around him? Check and ah how rare! All systems were a go and when he suggested we go to a music/food festival the following weekend I couldn’t help but be excited. The date started off pretty well but I couldn’t help thinking the guy was a bit of a bore. (Was I that hammered when I met him that he seemed funny; and was he that boring sober that he needed to drink in order to have a personality?) When we got to the wine tasting booth he seemed to come out of his shell and really hit it off with the woman pouring the drinks. As we walked back to our high top table nearby he told me that he “sorta used to date” her. Feeling a bit off guard I excused myself to the restroom to redo my pout. When I returned I found the wine girl, my date and lots of laughter at our small high top table. I put on the biggest smile I could muster and said “Hi, I’m Molly,” and extended my hand. She said, “Hi I am Katy, Jason’s girlfriend.” I looked at Jason in utter disbelief and confusion, to which he replied: “Um, we decided to give things another go while you were in the bathroom.” With that, I gracefully walked back to the wine bar and downed a flight of reds
-Molly
If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.
Give back while throwing down with the 
