If you can’t seal the deal after this date, something must have gone seriously wrong (let’s hope it wasn’t your art).
There is perhaps no easier winter date than at one of Chicago's fine tiki bars: immediately fun, warm, and cozy, the only way you can screw this up is to start talking politics.
Take your date to the next level with either a day trip to a local ski “resort” like Villa Olivia or the newly renovated Wilmot Mountain, or test your relationship with an overnight trip a bit further afield somewhere like Devil’s Head or Cascade Mountain.
We recommend Boyne Mountain for some of the best skiing in the area.
This may be a pricier option, but the real question is: Can you really handle 10 hours in the car together?
If your ideal date involves demonstrating what a stable genius you are, show off your deep base of useless knowledge at one of the many bar trivia nights around town.
As tempting as it may be to host a date in your apartment in the comforts of your (super-sexy) Cubs Snuggie, the dating world doesn’t go on hold just because the thermometers dip below zero.