Jess Downey

Q: What inspired you to start “All The Single Ladies” which features on ChicagoNow.com?

I kind of just fell into writing “All The Single Ladies.” I have always loved to write and I have been single for what seems like forever. Every time I had a crazy bad date story my friends would tell me that I needed to write about it and that I should submit it to some publication somewhere. I also kind of wanted to offer my own perspective on dating. For the longest time, I kind of felt alone because I always seemed to have really bad luck with dating and it all seemed so much easier for most of my friends. Over time I realized that when it comes to dating it doesn’t work the same for everyone and there is nothing wrong with that. So I started writing for Examiner.com and then I found ChicagoNow.com.


Q: What’s the one thing that sets singles in Chicago apart from others throughout the country?
It’s a pretty common idea that Midwesterners are “nice” and that we have those typical Midwestern values. I think in Chicago you get the city but you still get a certain flavor of that. Even though it’s the city I still see those sorts of values here. For example, I still have plenty of guys that actually come to my place to pick me up on a date. Not that it never happens any place else, but that’s something a lot of my friends in other cities complain about.


Q: Winters in the Windy City can be brutal on a person’s social life. Any tips for staying motivated to meet, mix and mingle?
If you live in Chicago, then you know how cold it gets here and you also know how to combat that. Personally I say just get out there and do it, don’t really even think about the cold. I mean, we brave the cold for everything else, so why not dating? Plus, winter is a pretty romantic season. Nothing beats cuddling up on the couch with a blanket and your crush. You can light tons of candles and watch movies all night. Candles are not nearly as fun in the summer.


Q: Any special singles events or groups that we should know about?
Chicago offers a ton of really fun speed dating events that people should always be on the look out for. For example, Drink Deck just helped to sponsor a speed dating shopping event which I thought was a really fun idea. Also, I am going to shamelessly promote myself here, I am in the early stages of planning another event which takes place in late Winter/early Spring.

Q: You’ve recently gotten involved with Project for Awesome. Can you tell us a little bit more about the organization and what led you to start volunteering?
I got involved with Project For Awesome because a fellow ChicagoNow blogger asked me to be a part of it and I was extremely excited when he did. It’s such a great thing. I chose to write about Deborah’s Place (http://www.deborahsplace.org/ ) which has been around for the past 25 years. It's a place that provides housing exclusively for women in Chicago and also aims to break the cycle of homelessness for women as well. Their goal is to provide supportive services to help women succeed in goals of stable housing, sustainable income and greater self-determination. I was inspired to volunteer partially from a fellow blogger friend, Bianca Marks, who writes about turning bad dates into good deeds (http://singleforgood.blogspot.com/) but then hearing about Project For Awesome has inspired me even more. I volunteered a ton when I was in college and always loved it. It’s my goal in 2011 to do it far more so I can give something back to society.


Q: How do you think Oprah has empowered single women, particularly those living in Chicago?
She’s a good example of how you can do all the things you want to do and still be single. She’s also a huge advocate for being happy and successful in life. But she encourages women to just be themselves and doesn’t make it seem like they have to be a certain way to gain that success and happiness. I would say Oprah definitely empowers single women to be happy and content and to not settle for less than what they deserve.


Q: Have you ever had a big oh-no moment?
I can actually think of a couple of oh-no moments and they have actually helped me to be a little more comfortable with who I am, which is kind of funny to me. One would actually be using my full real name while blogging which is something that I never really thought about. That was until I started talking to this one guy on OkCupid. He seemed very nice and we were both interested in each other. I told him a little about the blog and through simple googling he found me and my blog (it is so easy to find and apparently obvious it is me). I guess the blog kind of psyched him out and made him think I was this super expert dater who only wanted to be single so he refused to meet me. Now I realize that if a person can’t deal with the blog or at least ask me questions to get to know more about the blog then he probably isn’t for me.


Q: What’s the most important resolution for singles in 2011?
I would say the most important resolution for 2011 for any single person is to love yourself, maybe even vow to do something special for yourself every month or more often if you would like. I often feel that singles are the most hard on themselves especially after a really bad date. It’s important to love yourself so take a little time out to let yourself know that.

You can get the "dish" from Jessica by clicking on  All the Single Ladies!