Hey, Chicago Daters: Enter the “Woo the Wingman” Contest and Win a Hot Date!

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Editor’s note: This is a guest post from our friends at RedEye Chicago Dating, powered by HowAboutWe.

Friends, it’s getting crappy out there. I’m a single man and sometimes when the weather sucks, you just want a good cuddle, you know? So I signed up for our new dating service and thought it might be fun to do a little contest to make my experience interesting. Here’s how it’ll work.

1. Sign up for an account and get a feel for how it works. (Unlike regular dating sites, on RedEye Dating you pick the actual date you want to do.)

2. Check out my profile and come up with a date idea you think we’d both like to go on.

3. Propose a date for us to go on! You have to include #wingman after the date idea (i.e. How about we…go to a wine tasting at Webster Wine Bar #wingman).

That’s it! The winner gets to go out on a date with me and a dating prize pack (3-month membership for RedEye Dating, $50 Lettuce Entertain You gift card, $25 AMC Theatre gift card and 2 tickets to Zanies Comedy Club). Also, there might be that “deeply emotional soulmate connection” thing.

Sound good? Start submitting dates!

(If you need contest rules because you’re a boring person, you can find those here.)

Ernest Wilkins enjoys a good party. As social media/events producer for Chicago’s RedEye newspaper, it’s kind of his job. Voted one of the top singles in 2011 by Today’s Chicago Woman magazine and one of’s “11 Hot Chicago bachelors you need to meet”, he’s always in search of a good time (or a good story to tell the next day). A native Chicagoan, Ernest attended Florida State University and is willing to talk football whenever you’d like. Or not, that’s cool too.