Valentine’s Day Do’s & Don’ts When You’re Not Quite a Couple

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Valentine’s Day is for couples in love, but what if you’re not a couple yet? Here are some do’s and don’ts for handling the holiday when you’re in the early stages of a relationship. 

DO… Ask Them Out For The Big Day

If you see long-term potential for the two of you, straight up ask them out for Valentine’s Day. Love is already in the chilly February air, so tap into it. See it as a chance to get closer to your potential soulmate. 

DON’T… Get Stressed

The 14this just a day on a calendar. It doesn’t have to be awkward or stressful. If you decide that a date on V-day is not a big deal, then it won’t be a big deal to the other person, and you’ll both enjoy it more. 

DO… Ask Them Out The “Right” Way

Frame it as a Friday night date that just happens to fall on Valentine’s. And when you ask, add some humor to set the right tone and defuse potential awkwardness. Say something like, “Hey, let’s get together on Friday. It happens to be Valentine’s Day, but don’t worry—I won’t pop the question till our NEXT date.” 

DON’T… Overdo It

No lavish dinners. No romantic strolls. Instead, suggest an activity: ping-pong or karaoke or shooting pool. You’ll have way more fun than those couples stuck in stuffy, white-tablecloth restaurants being tormented by violin music. 

Candy HeartsDO… Go Out With A Group

If a one-on-one date feels too pressure-packed for you, do something with a larger group, such as pub trivia, board games with friends, or a double date. The group dynamic will ease tension and help you feel more relaxed and confident.  

DON’T… Bring Chocolates 

Avoid giving clichéd gifts like boxes of chocolates, roses, or Hallmark cards. 

DO… Bring Something Sweet

Homemade baked goods (brownies, cookies, cupcakes) make sweet surprises at this stage of dating. If you want to play it safe, pick up a decorated cupcake or cookie from your favorite neighborhood bakery or hand your new squeeze a tiny box of candy hearts. Anything you would have given your crush back in sixth grade makes a downright adorable gift today. 

DON’T… Quote Romantic Poetry

Want a better idea? You and your date can use this love-poem generator to craft a funny, intentionally flowery sonnet worthy of Shakespeare himself.  

Connell Barrett is a dating coach for The League and the founder of Follow him on Instagram at @datingtransformation.

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