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Five Ways to Make the First Move Before Valentine’s Day

By Lydia Gregovic

It’s natural to have love on the brain around this time of year. But the days leading up to February 14 can make even the most confident dater nervous thanks to the pressures often associated with the holiday, none of which set the tone for low-key dating. 

Instead of waiting to make the first move until after Cupid’s made his rounds, embrace the spirit of the season in a light-hearted way that takes the focus off candy and flowers and puts it back on what matters — the connections you’re making.

We know, we know. It’s easier said than done. To help ease anxieties, we’ve compiled some foolproof Valentine’s-themed first moves, designed to help you get the date you want without any of the unnecessary stress.

The Poetic Intro

“Roses are red, violets are blue
How about some drinks, and maybe dinner too?”

Talk about timeless! This cute twist on a classic valentine strikes the perfect chord between funny and sweet. Try our interpretation, or come up with your own; the possibilities are endless, especially if you’re the creative type. 

The No-nonsense Invitation

“So, what does your February 14th look like?”
“I’m looking for my Valentine, and you might be it!”

You can’t always get what you want, but you definitely don’t stand a chance if you don’t ask. While this method may seem a little bold to some, a direct question gets straight to the point, cutting out days of back-and-forth messages that lead nowhere. Expect to attract a guy or gal who’s up for an adventure, and who, like you, isn’t here to play games.

The Old-School Card

Love isn’t always serious, and Valentine’s Day shouldn’t have to be either. Kick off your convo with a pop-culture pun that’s not only sure to get a laugh a match but attract a potential partner who appreciates your offbeat sense of humor.

The “Would You Rather” Game

“Valentine’s Day: Overrated or romantic?”
“Candlelit dinner or laid-back movie night?”

Leading with a question is a great way to help ensure a match responds, but it also lets you get to know the person behind the profile. With slight adjustments, a tried-and-true icebreaker can spark an energetic conversation while helping you discover any common interests you and your future date may share.

The Hollywood Heavy-Hitter

“You had me at hello!” – Jerry Maguire
“Hey, how about…oh, how about some coffee or, you know, drinks or dinner or a movie…for as long as we both shall live?” – You’ve Got Mail

Having a hard time coming up with your own memorable one-liner? Borrow someone else’s! Hollywood is full of iconic quotes about love and romance, although you may want to hold off on sending Noah’s speech from ‘The Notebook’ until at least the second date. For best results, pick a flirty line from your favorite movie and test your match’s pop-culture knowledge.

And once you’re ready to ask your match out, here are our top tips. Good luck!