If weather conditions permit, going sledding or tobogganing is the perfect way to establish physical contact without crossing too many personal boundaries. It is also great exercise, and it may take the damper out of an otherwise bleak winter afternoon. Plus, it is way more exciting than the typical "coffee date!"
Build a snowman
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Sound silly? Consider that there’s something about reliving childhood activities that tends to conjure up feelings of nostalgia, comfort, playfulness, and warmth—all of which go a long way in alleviating dating fatigue or dread. If you find yourself having too much fun and don’t want the date to end, consider grabbing some soup afterwards to warm up and carry on some good conversation.
Visit a bakery and then spread some holiday cheer
My favorite date begins with stopping at your local bakery or coffee shop to purchase some hot chocolate and donuts to give away. Before doing so, set a reasonable budget (perhaps $20 between the two of you). Then step outside to whatever Winter Wonderland awaits you and share your goodies with strangers, the homeless, neighboring retailers, or whoever you know is in need. It’s a great way to observe your date’s social skills, and it’s a relatively selfless, pay-it-forward endeavor. This activity also takes some of the pressure and focus off of you and your date so you’re not stuck staring at each other across the table!
Assuming it’s a blustery winter day and going outside just isn’t an option, try picking out some new or unusual recipes and then make them together. There’s nothing like enjoying good comfort food on a cold winter’s night, and then snuggling up in front of a movie to digest.
Recreate your first (or pivotal) date, if you met during the winter
If your partner planned it the first time, perhaps you can plan it the second time. Be sure to add a few touches that demonstrate how the relationship has grown or how that first date was so instrumental in allowing the relationship to evolve.
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Volunteer together at a soup kitchen or homeless shelter
This activity not only allows you both to give back to your community, but you’re doing a good deed while getting to spend time with each other. It’s a win-win.
Keep in mind, this list just scratches the surface. There are endless possibilities when it comes to planning a winter date. Just don’t let them slip by!