Cupid shoots its arrow in the air every year, signaling to couples from all walks of life that February 14 is the day of love. Traditionally, Valentine’s Day is the day when men express their gratitude and appreciation for the women in their lives; whether they be a mother, sister, aunt, or romantic partner. The Day of Red Roses and Pink Hearts is dedicated to making the divine feminine feel special; however, there hasn’t been a time (outside of Father’s Day) when the divine masculine was celebrated in high regard — until now. Although the concept of Sweetest Day is fairly new, it has given women the opportunity to display romanticism towards their masculine other half; an act that men aren’t so privy to experiencing. 

What is Sweetest Day?

Sweetest Day is a holiday that is celebrated primarily in the Midwestern and Northeastern parts of the U.S. on the third Saturday in October. It is a day to share romantic deeds or expressions, and acts of charity and kindness for friends, family, and lovers. The holiday, which originated in Cleveland, Ohio in 1922, was planned by several candy makers who set out to distribute over 20,000 boxes of candy to “newsboys, orphans, old folks, and the poor” in the city. Since then, the holiday has spread to specific states in America such as Illinois, Detroit, Indiana, New York, Wisconsin, and Florida. 

No one truly knows how men became such a focal point in a holiday dedicated to showing love and affection to all genders, but the skepticism hasn’t discouraged anyone from celebrating their man of choice. 

Since becoming popularized in the Midwest, Sweetest Day and National Boyfriend Day (usually observed on October 3) have become the same. In the region, Sweetest Day is celebrated by women who treat the men in their lives with candies, gifts, and other thoughtful gestures. 

The holiday is celebrated annually on the third Saturday in October. This year, it falls on Saturday, Oct. 19.

In honor of Sweetest Day, here are some cute date ideas to partake in with your sweetie:

Sip & Paint at Home

Grab some small easels, a paintbrush set, and some wine glasses to get ready for a night in with your significant other. There’s no better time to have a nice, intimate conversation with your partner than a moment filled with creativity and a little beverage to set the mood. 

Shopping Spree

Women aren’t the only ones who enjoy looking good. Take your guy out on a nice little shopping trip. Allow him to pick out his favorite shoes, jogging suit, or cologne (all within your preferred budget of course). Nothing says “I love you” more than a new Nike Tech suit. 

Sports Event Date

Football season is unfortunately amongst us ladies — but this isn’t entirely the end of the world. Now is your chance to purchase those Cubs tickets your husband has been keeping his eyes on for the past few days. You may not necessarily want to attend the game, but he would appreciate the thought of you participating in such an activity with him.

Plan a Weekend Getaway

If your significant other has been hinting at needing a vacation, Sweetest Day would be the perfect occasion to pack your bags and head to the airport. Airfare prices tend to surge drastically during the holiday season, and since Sweetest Day is a month before, it’s best to book that trip to Arizona or the Virgin Islands pretty soon. Romantic, ocean-view getaways? Sounds like the perfect Sweetest Day gift ever. 

Whichever way you decide to celebrate your significant other, remember to make sure the gesture is coming from the heart and that they feel the most important on such a romantic occasion.