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Dating Apps Messaging & Tips Men & Women
Are you unsure how to text a woman on a dating app?
Knowing what to say, how to reply, and how to keep her interested can make the difference between a conversation that dies and one that leads to a date.
This guide shows real examples of texts with women, explains what works and what doesn’t, and teaches you how to text with confidence, playfulness, and respect.
Whether you want to start a conversation, create fun banter, or build trust step by step, these tips will help you text women effectively, stand out from other men, and get better results on dating apps.
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Example 1: “If I Win, You Owe Me a Date”
• The guy texts: “If I win, you owe me a date.”
• Many men make the mistake of treating women like the prize. They think a “win” is getting a date.
• Confident men focus on what they bring to the table and look for women who match their energy. They see both people as having value.
• When she replies “Smooth lol,” it is not real interest. She is giving a small compliment but hasn’t emotionally invested yet.
• A playful, unexpected line like “Julia sometimes it’s about thinking outside the box” moves the conversation forward. It shows confidence and playfulness and helps her feel open to a date.
Image credit: dude-hack.com
Example 2: Playful Challenge and Banter
“Have you tried ‘I’m not short, I’m vertically challenged?’”
• It is not the lightest opener, but challenging her playfully shows confidence and that you are not afraid of her reaction.
• Her “very smooth” is sarcastic. Do not apologise for your humour; if she does not like it, it is better to know early.
• Using playful role reversal like “Woah, woah this is moving too fast” makes the conversation fun and different from most guys.
• Even if she snaps or seems offended, using clever, confident banter shows intelligence and emotional grounding.
• If she is secure, she will laugh, feel comfortable, and be open to getting to know you better.
Image credit: dude-hack.com
Example 3: Avoid Overstepping and Build Trust
• Guy says: “That’ll probably drop to second after I’ve visited your place.”
• He is coming on too strong.
• Talking about intimacy too early makes most women feel unsafe.
• She probably already feels uncomfortable and may be annoyed.
• Hannah’s “Damn that was smooth” is not a real compliment. She is keeping things calm because she feels unsafe.
• Men often make the mistake of boasting about intimacy or “size.” Women hear this all the time on dating apps, and it makes you sound like every other guy.
• When she says “How are you this smooth,” she is pretending again — she has already lost interest.
• The right approach is to joke, banter, be different from most guys, and take it step by step.
• Build the connection gradually, getting to know each other step by step.
• Make sure she always feels safe.
• Once both of you feel comfortable, you can see if things should move forward naturally.
Image credit: dude-hack.com
Example 4: “How Short, Creative Messages Help You Stand Out on Dating Apps”
1. Keep your messages short.
The man did well by splitting his thought into two short messages instead of one long paragraph.
Share one clear point and then pause so she has space to respond.
2. Send one or two messages, then wait. If she doesn’t reply, avoid pushing the conversation.
Most of the time, no response simply means she’s not interested — and that’s okay. Notice it, learn from it, and move forward.
3. Creativity helps you stand out
Women receive repetitive messages constantly, so something light, fun, and respectful instantly feels different.
4. Her “eye roll” wasn’t rejection
Kat’s reaction meant: “Here we go again… but that was actually funny.”
It broke through her initial guard and made her laugh, which helped her feel more comfortable and open.
5. Her final emojis showed real comfort. Her laughing and shy emojis signalled that she relaxed and enjoyed the exchange.
When a woman feels safe and entertained, the conversation naturally moves in a better direction.
Image credit: dude-hack.com
Example 5: “Confidence, Curiosity & Secure Masculinity"
1. Don’t “Choose” Her Before You Know Her
Saying things like “I’m just saying I would date you” makes it seem like you’ve already decided she’s the one — based only on looks.
A better mindset:
“She seems interesting. I want to get to know her step by step and see how things unfold.”
2. Never Apologize for Being Bold
“Sorry if I’m too bold” reads as insecure.
Instead, keep it playful and confident:
“Too bold, eh? 😜”
Boldness isn’t a problem — insecurity is.
3. Don’t Make It All About Her Looks
Men are more visual. Attraction matters.
But secure men know:
Physical attraction gets your attention.
Her character earns your commitment.
Who she is matters more than how she looks.
Example 6: “How To End A Conversation On Dating Apps
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Asking “Wanna come over and watch a film” too early can feel rushed and make her uncomfortable.
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If she replies, “I’m working tonight lol,” that’s a clear signal to end the conversation. Do not send another message.
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Staying quiet won’t always bring her back. If she’s already showing low interest, she’s likely not a good match. Take it as a sign to move forward with someone more aligned.
Photo Credit: datingmetrics.com
Example 8: “Be Playful & Straight-Forward”
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Lyle messaged Jackie unexpectedly to ask her out for lunch. In dating, predictable moments create comfort, while unexpected moments increase excitement and passion.
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Jackie made it playful by replying, “This is her assistant. I’ll check Jackie’s schedule.”
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She then tested him with, “I may be busy with my chocolate-bearing suitors,” showing she liked him and wanted him to pass.
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Lyle handled it perfectly by joking, “Is there a place on your walking route we can get chocolate? I’m concerned about chain-of-custody issues if I buy it beforehand.”
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Jackie’s kiss emoji showed she appreciated how he made her feel and felt connected.
Photo Credit: thefemininewoman.com
Example 4: “How Short, Creative Messages Help You Stand Out on Dating Apps”
1. Keep your messages short.
The man did well by splitting his thought into two short messages instead of one long paragraph.
Share one clear point and then pause so she has space to respond.
2. Send one or two messages, then wait. If she doesn’t reply, avoid pushing the conversation.
Most of the time, no response simply means she’s not interested — and that’s okay. Notice it, learn from it, and move forward.
3. Creativity helps you stand out
Women receive repetitive messages constantly, so something light, fun, and respectful instantly feels different.
4. Her “eye roll” wasn’t rejection
Kat’s reaction meant: “Here we go again… but that was actually funny.”
It broke through her initial guard and made her laugh, which helped her feel more comfortable and open.
5. Her final emojis showed real comfort. Her laughing and shy emojis signalled that she relaxed and enjoyed the exchange.
When a woman feels safe and entertained, the conversation naturally moves in a better direction.
Image credit: dude-hack.com
Example 9: “How To Create Curiosity When Messaging a Woman You Want To Date”
11. A message like “The dog in your last pic reminded me of something!” isn’t perfect, but it still creates curiosity and feels light and different — which already makes you stand out from guys who say “hey” or “you’re beautiful.”
Curiosity works well in early messages because it’s playful without being pushy and invites her to lean in.
2. Avoid filler words like “Well,” which can sound unsure. Getting straight to the point feels more confident.
3. A stronger version would be:
“I had the EXACT same one when I was living in Italy! Mine loved the snow, especially in the Alps 🙂”
Photo Credit: road.dating/blog
Example 10: “Avoiding Neediness in Dating App Messages”
1. Using too many exclamation marks makes you look overly eager.
It can feel like you’re trying too hard for her approval.
2. Calling her job “cute” and jumping to a “magic kiss” comment is too intimate too soon.
This often makes women feel uncomfortable or unsafe.
3. He also puts himself in the position of hoping she’ll “give” him something with the "magic kiss" part.
That shows insecurity instead of confidence.
4. A better approach is simple:
Share a little, ask a little, and build connection step by step.
Show that you bring value too.
Photo Credit: roast.datingblogtinder-texting-guide
Example 11: “Jokingly Teasing”
1. : "It's flipping dope yea!"
Shows excitement for his own life, not trying to impress her.
2. "Can't say I don't like mountains!"
She’s smiling and engaging, showing interest in his world.
3. "You're more into skiing or snowboarding?"
Focuses on her in a calm, chill way. Using “You're” instead of “Are you” keeps it relaxed.
4. "Skiing for sure!"
She shows interest and is joining in.
5. He jokes: "Ah sorry, can't work between us. Snowboard team here."
Playful selectivity makes him appear confident. Always keep it light so she feels safe.
6. She responds: "Noo! I can snowboard though!"
It’s fun to see a woman playfully chase the man, creating connection and energy.
Photo Credit: roast.datingblogtinder-texting-guide
Example 13: “Too Eager Messaging A Woman You Want To Date?”
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This guy wrote way too much.
Keep messages short.
One point at a time, and wait for her reply.
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He got intimate too soon.
Talking about height, confidence, and “excitement” is too much for early messaging.
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He acted like he’ll be whatever she needs.
You offer what you offer — you’re not her server.
If you start this way, the dynamic will stay that way.
Keep it simple, confident, and steady.
Example 13: “Dating Text Analysis & Tips: Not Holding His Own”
He thanks her for letting him know she got home — sounds like she did him a favour.
Better: “All in one piece? 😜”
“I HOPE you had a good time” — don’t hope they like you, focus on your own experience.
“I’d love to see you again if you’re down” — using “LOVE” and “if you’re down” adds pressure.
Try playful alternatives or wait for her to suggest the next date.
Set the next in-person date at the end of the current one: “When are you free again?”
Keep texting minimal until then.
“I appreciate you coming down to meet up” — putting her on a pedestal signals low confidence.
Stay playful, light, and value yourself.
