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There’s still enough time to plan the perfect Valentine’s Day so you can skip the usual dinner and drinks and try something new. Dapper Man offers three unforgettable dates you’ll both love.


Maybe your Manhattan or Old Fashioned taste just fine, but wouldn’t it be great if it were better than just fine? Taking a mixology class is the perfect way to do that, and then your partner can be a pro at making them too. Like most classes, you two will be given a chance to learn something new and bond over it together, but most importantly you’ll both be able to impress the next time you host a dinner party. Or maybe challenge each other to see who can make the best mixed drink.

Try: The Violet Hour | (773) 252-1500

Whenever there’s alcohol involved there’s always a risk of things getting messy so keep it casual with some dark fitted jeans and a simple button up. Make sure to wear some comfortable shoes since you’ll likely be standing for a long time. A nice pair of boots will do the trick.


Men are starting to embrace the spa life more and more and it’s no wonder. You’ll both have a chance to unwind and relax so grab a day pass and get side-by-side massages, try a facial, and hit the sauna. You two can enjoy each other’s company while unplugging from the rest of the world and revel in the peace.

Try: Red Square Spa | (773) 227-2284

Most spas will offer complimentary robes for your stay but if you aren’t too into all that freedom feel free to keep your underwear on, just avoid bathing shorts.The spa is all about being comfortable and they often encourage you to wear nonrestrictive clothing so joggers and a T-shirt will be enough for your trip there but pack a fresh set of clothes for the trip home since no one likes the feel of worn-in clothes after all that pampering.


If you really want to impress, a helicopter tour of the city will definitely do the trick. Aim for a tour around sunset to still see all the details of the city but then be dazzled by the bright lights as well. It’s a great opportunity to point out all the different locations around town that hold significant meaning for your relationship and to see everything from a new angle. After the tour you can end the night at a classy restaurant

Try: Chicago Helicopter Experience | (312) 967-8687 OR  Celeste | (312) 828-9000

You’ll want to dress to impress for this romantic date. When you’re that high above nothing will make you feel more striking than a well fitted suit. Keep it relaxed and cozy with a turtleneck. Try out our Date Night suit for the right look.

Book an appointmentfor the look today.


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