Date Ideas for Cuffing Season


Feel that chill? Winter is here and along with it is baking, decorations, and the growing temptation to stay in bed all day. Ideally with a special someone. 

Love it or hate it, cuffing season is upon us. From instagram hard launches to couples walking down the street, there’s no denying it: the summer flings are morphing into serious relationships. Maybe it’s the urge to bring someone to meet the parents for the holidays. Maybe a people just want a warmer bed. Or maybe everyone is having great couple costume ideas they want to try. Who knows? All we know is around October the dating attitude shifts in a wholesome, relationship-oriented direction.

The busy summer months offered many date options: concerts, picnics, beach days. When the weather is nice even a walk in the city park with some coffee is romantic. 

However, with the encroaching sweater weather, singles— on dating apps and elsewhere— are craving wholesome, seasonal, and weather-appropriate dates. While these dates may be more effort, that doesn’t mean less enjoyable. 

Read below for our top-tier cuffing season date ideas. Do one on it’s own or combine a few to make a whole day out of it. 


Gingerbread House Making


This delicious activity is a perfect way to bond. You can buy inexpensive gingerbread house sets from most grocery stores, or if you’re a go-getter (and want to spend more time with your date) you can try making the cookie sheets from scratch. Using icing, candies, and sprinkles, let the creativity (and conversation) flow. You can build one together and connect over the struggle, or raise the tension with some flirty competition. It smells good, looks good, and if you’re the impatient type, tastes good. 


Halloween//Christmas Decoration Drive


Wether it’s an organized park light show or just a cruising through a nice neighborhood, holiday decorations are a guaranteed romantic setting. Go the extra mile by planning an on-theme playlist ahead of time. Preferably with songs you can both sing along to. It’s an activity that’s passive but not boring, and you can chit-chat choosing which decorations are your favorites. Driving around is also a nice balance of having some privacy to talk before going to each other’s homes. 


Hot Chocolate


Anything warm and sweet is sure to please this time of year. Hot chocolate is something easy to make and easier to customize. It doesn’t have to be basic either. There’s tons of hot chocolate recipes that even the worst chef can manage. Stock up on flavors, marshmallows, and  toppings. Once your treats are ready, you can cheers and sip while watching a movie, playing a board game, or any other activity on this list. 


Scary Movie Marathon


Also possible with Christmas movies for the faint-hearted among us, curling up on the couch while the cold wind blows outside is unbeatable. Make sure to vet your movie choices, as well as your dates comfort level to avoid any extreme frights. With a warm drink and a soft blanket, this can be a great 3rd or 4th date idea once you have had the first getting-to-know-each-other conversations. 


Pumpkin Carving


You can’t beat a classic. Pumpkin-carving is fun, challenging, and you both end up with a great souvenir. Even if you’ve never done it before, once you have the pumpkin gutted it’s easy to let your  creativity run wild. You can help each other with the hard parts and have fun doing it. As a post-game treat you can easily roast up the pumpkin seeds in some salt and oil.


Ice Skating


If you want to live out your Hallmark-movie dreams, look up your nearest ice-rink and get two tickets. If one of you is a novice, the other can help you learn as an excuse to hold hands while doing your best not to fall down. This may be the most active date idea on the list, so it may be best to pair it with something more low-key before or after.


Board Games


If you’re escaping the cold but want something more engaging than sitting with a coffee, a board game night is a perfect solution. Pick the right board games that you think will prompt conversation and connection. This can be a perfect way to break the tension and spend time together without any initial awkwardness. 


S’more Making


Enjoy the warmth of a fireplace or bonfire as well as one of the best treats in the form of graham crackers, marshmallows and chocolate. Putting these together is an activity all on it’s own, and it’s impossible not to giggle while trying to eat them without making a mess. Something this fun is a great way to break the tension and feel more comfortable around each other in the early dating stages.


There you have eight great date ideas for cuffing season. Yes, a large percentage of them are food-based, but what is winter for if not indulging? Happy cuffing season, and best of luck!


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