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How to Casually Text a Guy: No Pressure Ways to Reach Out to Him for the First Time

Sarah stared at her phone. Her fingers hovered over the keyboard. For weeks, she’d wanted to message Michael – that cute artist friend on Facebook. His paintings captured beauty in every stroke. Their posts showed they had so much in common – nature, offbeat movies, even quirky puns.

But sending that first text felt more daunting than climbing a mountain. What if he didn’t respond or wasn’t interested? The possibility of rejection made her chest tighten with anxiety. Sure, she’d matched with plenty of guys on dating apps. But messaging a digital friend she’d never met in-person? It felt higher stakes. Much higher stakes for someone she had an undeniable crush on.

When You're Trying to Play It Cool but Accidentally Send a Heart-Eyed Emoji Meme

Can you relate? You’re really not alone here. That first romantic text can feel weightier than it should. But don’t fret. I’ll share some low-pressure, natural ways to slide into their DMs and get a conversation flowing. With some tips and examples, you’ll make that opening move feeling cool and collected.

How to Send a Casual Message to a Guy

Mention a Mutual Friend

Bringing up a mutual friend is an easy icebreaker – “Hey, I ran into Taylor the other day. She mentioned you’ve been super busy with your new job. How’s that going?” It makes conversation feel natural and connected.

Follow Up on Something He Previously Mentioned

If they’ve posted about an event or interest, follow up – “I saw you went to that concert! How was it? I’m jealous, I heard they put on an amazing show.” Shows you were paying attention.

Point Out a Shared Interest

Having common ground gives you an instant topic to start a conversation. If you notice you’re both fans of the same band, author, game, etc. use that to break the ice. “No way, you’re obsessed with Elden Ring too? Who’s been your favorite boss to beat so far?” You’ve now established rapport over a mutual interest.

Initiate a Discussion About Current Events

Is there a buzzworthy news story, TV show premiere, or viral video you know he’d have thoughts on? Bring it up! “Ok I need your hot take – did you see that outrageous ending to the season finale last night?” Cultural topics make for fun, lighter discussions that open the way to a low-pressure conversation.

Seek Advice or Recommendations

If he’s an authority on a subject you’re interested in, ask his opinion to flatter his expertise. “You’ve been all over Europe, right? If you had to pick one city for me to visit for the first time, which would you recommend?” This is an easy way to keep things lighthearted while learning more about him.

Ask an Intriguing Question

Pose a fun, imaginative “what if” scenario related to his interests or passions. This gets his creative mental gears turning in an engaging way. For example, if he’s really into art, you could ask something like: “Quick, you’ve been appointed as the curator for a huge gallery exhibition – but you can only display pieces illustrating a single color. Which color do you choose and why?”

Send a Group Text

Having a few other friends included can help relieve some of the pressure in those first exchanges. Just make it low-key – ask for recommendations, share a funny meme, or coordinate making group plans. “My friends and I are trying to check out that new rock climbing place next week if you’re interested in joining!”

Give Him a Challenge

Keeping things playful with a lighthearted game or dare appeals to people’s innate sense of competition. “Ok I’m putting you on the spot – you have to decide between crunchy or smooth peanut butter. Go!” Or “I dare you to send me your best impersonation of a celebrity by the end of the day!”

Share an Inside Joke

If you already have some silly ongoing joke between you two, bring that up! This continues your friendly rapport. “Did you see they opened a new artisanal pickle store downtown? I know how excited you must be!” Those shared laughs make conversation feel easy.

Offer a Genuine Compliment

Provided you’re being authentically nice and not over-the-top, a well-placed compliment can be a warm way to start a chat. “I noticed you finished another of your paintings – the colors and textures you used are gorgeous! You’re so talented.” People love feeling appreciated.

Inquire About His Interests

If you notice him posting about a hobby, accomplishment, or activity, ask him for more details! “Your hiking photos are unreal. What’s been your favorite scenic trail so far?” This flatters his passions while allowing him to discuss something he’s excited about.

Extend an Invitation

Rather than seeming meticulously planned, you can make this sound spontaneous and casual. “Hey, I’m going to be grabbing coffee over by you in a little while if you’d want to join?” Now you’ve opened the door to spending time together without any awkwardness.

Tease Him a Little

Once some playful rapport has been established, you can try out some light flirtatious banter. “I see you finally got around to doing laundry… did you remember to separate your colors from your whites this time?” Just keep it good-natured and avoid anything too heavy-handed or uncomfortable.

Ask Him Out

When Your Crush Suggests Meeting Up but Your Introverted Side is Screaming Cancel Meme

Or, you can be more direct but casual: “I’ve really enjoyed getting to know you, and I think you’re great. Want to grab drinks this week?” A straightforward invitation done right.

Be Upfront

Similarly – “I’ve low-key had my eye on you for a while. Interested in grabbing dinner soon?” A breezy, sincere approach shows confidence.


From my professional experience as a relationship coach, let me give you a off-angled perspective. It’s already the digital age, sliding into someone’s DMs or messaging people you don’t know well is extremely typical behavior. Some people fully expect and are very used to being approached this way. It’s simply how many connections start nowadays – after all, it’s easy to say hi to anyone with just a few taps on your phone.

Sending Explicit Photos Web of Consequences Meme

So the good news is, there’s generally far less inherent pressure or awkwardness in reaching out over text than there used to be. Those fears and anxieties you might be feeling? For the most part, they’re just in your head. Shooting your shot via message is widely accepted as normal protocol these days.

However, the truth is the rejection rate when messaging someone new is still quite high. People can be skeptical of random texts. They may worry about intentions or even being catfished. An unfortunate reality, but don’t take it personally if you don’t get an enthusiastic response right away. Brush it off and try again another time with someone new.

The key is keeping your opener breezy, finding authentic common ground to bond over, and making the overall vibe feel light, casual and no-pressure – exactly what we covered with all those conversation starter examples. When you nail the tone and message someone with a warm, sincere approach, you’re far more likely to receive a warm response in kind and kick things off on the right foot.

So go ahead, be brave and make that first move! Whether mentioning a mutual friend, cracking an inside joke, or extending an invitation their way, you’ve got all the tools to slide into their DMs feeling calm and confident. Take a deep breath, channel your coolest self, and don’t psych yourself out beforehand. After all, you’ll never discover what could blossom from taking that first step if you don’t try.

Because who knows? That internal hurdle you’re struggling with today might become an afterthought once you look back on how your love story began. An initial text that felt intimidating at the time may end up being a hilarious anecdote you’ll laugh about together years down the line. All it takes is being bold enough to break the ice.

Have any other tried-and-true texting tips or success stories to share? I’d love to hear your experiences in the comments! And if this advice resonated, don’t forget to pass it along to any friends who could use a little messaging motivation and support themselves.

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