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Flirting Archives

Groupon sets the new Guinness World Records title for speed dating (and I was there)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Last night Groupon set the new Guinness World Records title for speed dating at the Paris Club in River North. The original record was 313 daters at an even in Hoboken, New Jersey. In Chicago, there were 414 total daters at the event who participated in at least 20 three-minute-long dates. And I was lucky bachelorette number 166.
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Guest post: Oh the weather outside is frightful...

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

A few weeks ago I wrote a guest post for a website called Cupid's Pulse. Well, I am super excited because one of their very awesome writers has so graciously volunteered to guest post for my blog as well. This post comes from Erika Mionis who is a staff writer at Cupid's Pulse. Erika is a student in Arizona who hopes to pursue a career in journalism. 

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In defense of the shy guy

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

Man in boxers crouching

Recently I made a new friend. I kind of use the term friend loosely here as I have been engaging in a little flirtation with him. Read that as I have been flirting my ass off. He knows it and it seems to be pretty mutual.

Anyway, upon getting to know this guy, he has openly admitted to me on more than one occasion that he is a really shy guy - actually to be technical here he is a shy guy who is also on the clean cut side. This is generally the kind of guy that I have a really hard time meshing with and I know it's a problem for other women too.

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Date Night Challenge Week 3: Things haven't gone the way I planned (yet)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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So it's week three of the Date Night Challenge. And this week I actually had a date lined up. I say that like I am a little school girl or something but I was actually pretty excited. Frankly, there has been a shortage of really awesome guys asking me out on dates lately - I am not sure why that is.

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