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Great Winter Date Ideas

Dr. Jess     
Heat up your love life even in the coolest temperatures with these expert dating tips.

As the cold weather creeps in, you may feel enticed to stay at home under the covers all day. However, if you have a big date coming up or want to reignite the spark with your lover, impress them with a creative activity, rather than the inside of your apartment.

I chatted with dating experts Carmelia Ray and Deanna Cobden to get inspired with some great winter date ideas!

Can you suggest some ideas for fun, economically-friendly dates?

"Ice Skating is a classic but still very romantic. There’s something about holding hands while skating that can melt a girl’s heart. Don’t forget to bring along a thermos of hot chocolate to warm you up after. Staying in can be fun too; light some candles, get a bottle of wine, add snacks, snuggle up under a blanket and have a winter-themed movie marathon." - Deanna

What are some indoor date ideas you would suggest for the winter season?

"Many cities offer Paint Nights, usually held at a wine bar or lounge, and they include all art supplies and canvases. You don’t have to be an artist, just show up ready to drink some wine, be playful, and at the end of the night you have a cool souvenir of your date to take home with you." - Deanna

"Volunteer at an animal shelter, homeless shelter or soup kitchen to spend time helping the less fortunate. It's amazing how the act of giving as a couple can create a closer bond and memorable experience." - Carmelia 

"Taste Test Date - Choose a random cocktail that you’re both into, like a Whiskey Sour or Sidecar and go to three different places to see which you like best. If you aren’t into drinking you can substitute it with something else, like cupcakes or holiday cookies from three different bakeries." - Deanna

It’s a beautiful Winter day. Any fun outdoor winter activities you could take your date on?

"Have an outdoor campfire (with an outdoor fireplace you can purchase at a Home Depot or Rona) and make s'mores! This type of date allows the couple to really get close to one another and provides an opportunity to cuddle if it gets chilly." - Carmelia

"If you’re near the mountains, snowshoeing and fondue are fun options. Fresh mountain air, a workout and warming up in the lodge after with a glass of wine and fondue or hot chocolate is hard to beat." - Deanna

Deanna Cobden is a dating and relationships expert for Carmelia Ray is an online dating and matchmaking expert at

Dr. Jess

"An award-winning speaker, Jess has worked with thousands of couples from all corners of the globe to transform their relationships via her wildly successful Marriage As A Business program. From Prague and Istanbul to Albuquerque and New York City, her relationship retreats receive rave reviews from some of the most powerful couples in the world who are drawn to her enthusiastic, practical and no-nonsense approach to happily ever after. Jess's doctoral research focused on sexual health and relationship education and she is passionate about accessible, classroom-based education. When she isn't globetrotting for speaking engagements, she volunteers with students, teachers and social service organizations to empower young people to embrace healthy, happy relationships. As a global ambassador for several brands, Jess contributes regularly to the biggest names in international media. You'll find her advice weekly in the likes of Women's Health, Men's Fitness, Cosmopolitan, SELF, Showtime and The Movie Network. Her insights into couple' issues reaches millions of homes across America as the host of the hit reality series Swing, which just capped its fifth season on PlayboyTV. Canadian-born and Chinese-Jamaican and Irish by descent, Dr. Jess loves ultimate frisbee, crab, airplane turbulence, cheese and red wine. Makes perfect sense, right?"
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