Sending The First Message: 5 Flirty Texts To Kick Off A Chat With A Match

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Blog Article: Texting

In dating, why does it always feel difficult to figure out what to say or text? We tend to get shoved in our heads before sending that first text message. Why? We try too hard to be witty or clever. Wit is wonderful, but that opening text message doesn’t have to be brilliant. You don’t need to be Shakespeare. You just need to be playful and clear. Clarity is huge. It’s important to let the other person know you’re interested. Clever is overrated, and clarity is underrated. Lower the bar for how funny, witty, or perfect your opener has to be. This will in turn relax you and unlock your most charming self.

If you have just matched on The League and are nervous about sending that first message, here are five flirty first texts to get you started. 

1. Foodie Flirt

FLIRTY FIRST TEXT: “I need to ask you a very deep, serious question, and your answer will have huge consequences for both of us… Thin-crust or deep-dish? 🍕”

WHY IT’S GOOD: “This silly, subversive text creates tension. Your crush thinks you’re about to ask a serious question, but you then release that tension by asking about pizza. It will make them laugh while leading to a fun topic.

2. #GoodDay  

FLIRTY FIRST TEXT: “Wow, this was shaping up to be just another [day of the week]—and then I matched with you. #GoodDay”

WHY IT’S GOOD: Being funny or witty is great, but sometimes vulnerability is the best way to make an impression. This text lets you “put yourself out there,” which is very attractive.

3. Personal Q & A

FLIRTY FIRST TEXT: “I see that you’re into [hobby/interest]. What do you love most about it?”

WHY IT’S GOOD: This is a great first message on a dating-app because everyone’s favorite subject is themselves. We all love to talk about our passions and hobbies, so it’s very likely to kick-start a stimulating conversation. It also shows that you took the time to look at their bio and are genuinely interested in getting to know them. 

4. Green Light

FLIRTY FIRST TEXT: “Should I make the first move, or would you prefer to wait for inspiration?”

WHY IT’S GOOD: “This lets your new crush know you’re interested, but you also give them the gift of taking the lead. Some people need a signal that they should ask you out, and this gives them that green light.”

5. Pop Quiz

FLIRTY FIRST TEXT: “Pop quiz! I’m texting you because… a) you’re adorable b) just saying hello c) all of the above.”

WHY IT’S GOOD: Everyone loves quizzes, and this text lets you be both flirty and engaging.

Connell Barrett is a dating coach with The League, founder of Dating Transformation, and author of the forthcoming book, Dating Sucks But You Don’t: The Modern Guy’s Guide to Total Confidence, Romantic Connection, and Finding the Perfect Partner.

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