
Whiskey and Cupcakes. Check out I Wish... for details on class dates and locations for when you and your sweetie can pop in for a beginner's guide on different varieties of whiskey and learn how it's made and aged. This one is an obvious win/win. Whiskey...and cupcakes...paired. Need I go on?
Rev his engine. What's more romantic than walking around looking at cars all day? Sigh. But if you're strategic about your approach and timing, the Chicago Auto Show is quite the social event. Check out their event schedule and plan accordingly.
Sweet tooth. We all know that the words "chocolate" and "valentine" are basically synonymous, but for some reason you can't talk your guy into doing the Chicago chocolate tour. What's a girl to do? Fergie said it best: Tell him to meet you half way. Order up some of Truffle Truffle's guy-friendly sweets including beer & pretzel flavored truffles, and maple bacon or bourbon pecan caramels.
If you need the romance (and if you're a high roller). Check out the "Be Mine" package at The Trump. For $575 per night, cozy up in one of the Trump's lavish hotel rooms, along with a few perks including: a bottle of Veuve, house-made truffles and in-room breakfast. While you're there, why not splurge on an in-room couple's massage? He's worth it...right?
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