Are you interested in maximum snuggling on a blustery November morning? Do you want a date to hang with in the corner and rip shots at your office Christmas party? Are you going to shut down your aunt's crap at Thanksgiving about whether you're "seeing someone"?
If you answered yes to any of these, this column is for you! Yes friends, it's time for your 2012 Cuffing Season preview. Allow me to take you through all the majesty and splendor of your aggressive attempts to lock down—or "cuff"—someone to cuddle with when it gets cold.
As you know, Cuffing Season—aka the Home Stretch—is the final two months of the Chicago dating season (which lasts from St. Patrick's Day until Halloween). Look at it like the playoffs: You've been doing some serious flirting all summer—but now? It's a whole new ballgame. After studying hours of film, I've got five tips to get you in the game.
1. Remain confident
Like so many blows to the head in football will lead to a concussion, so many "#ThisIsWhyImSingle" social media posts and negative self-talk will put you down for the count. It's simple: You deserve someone who makes you happy. Yes, you. Attack the world with enthusiasm. That's your mantra for the rest of the season. Know how we all have that super-dope version of ourselves in our minds? Be that person! You already are! Sorry to get all Steve Harvey on you, but it's true.
2. Your initials are DFW
Down. For. Whatever. Get out of your house and get to meeting people. College friend is in town at a bar? Go. Roommate is taking a trip back to his alma mater for a football game? Go. Bunch of people eating weed cookies in a co-worker's backyard? Don't go. Marijuana is illegal! You shouldn't be around those types.
3. Don't whine like Drake
This is a game of forward advancement. How many times have you seen friends keep that burlap sack of an ex around for when they're feeling lonely? That's an amateur move. If you're that person, get a backbone and move on. There's no reason for you to be calling or texting "Hey, How r u?" at 2:30 a.m, you sad human being, you.
4. Stay on offense
I can't tell you how many multiple-degreed people I know who act like second-graders when it comes to dating. "Oh, I've got to wait for the third time we Gchat each other before I can talk about going on a second date." What kind of backwater folk tale did your parents lay on you? You wanna go on a date? ASK TO GO ON A DATE! That goes for ladies, too. Any tightwad who would be turned off by you asking him out probably is a terrible lay. If you want to hang out? Say, "I want to hang out with you. What is your schedule?"
5. Be OK with singlehood
Dan Marino never won the big one. Neither did Charles Barkley. They're both still legendary. If you aren't finding suitable options out here, then sit the rest of the season out. Nothing is wrong with you ... that is, unless you've put up some sort of ridiculously high standard for yourself as a security blanket to avoid being hurt. What, are you Linus? Go read tip one again.
It's a long road until the end of the season. Keep your head together and you'll be a dating all-star by Halloween!
Ernest Wilkins is Chicago's wingman. email@example.com
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