7 Things Women Don't Realize They Do When They Text That Make Men Feel Weird

Here's how to save that awkward text conversation.

Woman texting man. Kaboompics.com | Canva
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Do you struggle with how to start conversations on dating apps or online dating? This isn’t brain surgery, yet so many singles find it hard to create a fun exchange. No matter what your age is, texting can be a fun introduction to someone new — if you know how to do it. One of my clients always started texting by asking about a man’s job, how his week was going, or where he grew up.

These uninspired openers didn’t do much to get the conversation going. These types of questions are not engaging, won’t get a man’s attention, and often result in one-word answers. If you want more men to respond, be attracted, and inspire your conversation to go beyond a few texts to get a date, you need to spice up your game. If you find your texts leave you with sporadic texting that trails off, no dates, and frustrated, you're probably making some serious texting mistakes. 

Here are things women don't realize they do when they text that make men feel weird:

1. You attempt to "qualify" a man via text

women who attempt to qualify a man via text makes men feel weird MART PRODUCTION | Pexels

The point of texting is to create a fun exchange that makes the man want to meet you. That will never happen if you try to vet him through your initial texts.

Don’t ask him where he went to school, what kind of job he has, or where he lives. That’s not entertaining.

Stop investigating, and instead have a little fun. Be curious about him and find out how he spends his free time. When you keep it light and fun, you’ll entice a man to want to know more about you, talk on the phone, and then meet.

2015 research suggests that women might benefit from keeping text conversations light and positive, particularly in the early stages of dating or when building rapport. This approach can foster a more approachable and friendly image, reduce the potential for misinterpretations, and generally create a more positive dynamic in the interaction.

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2. You text brief or one-word answers back to him

women who text brief one word answers or simple questions make men feel weird Michael Burrows | Pexels

If you want to get a conversation going, you need to engage the other person. Your short greetings or responses won’t cut it.

Take the question, “How’s your week going?” for example. What can he say but “good”? That kind of inquiry doesn’t lead anywhere.

It also helps to finish your response to him by asking another question. Make it easy for the guy to keep chatting because he might not know what to text either.

Research does not definitively state that women should not ask simple questions through text. However, a 2018 study found that some perspectives suggest that doing so can sometimes be perceived as less assertive or could lead to misunderstandings due to the lack of nonverbal cues in text communication. This can impact how a message is interpreted, regardless of gender. 

RELATED: 18 Texts Men Send Women — And What They Really Mean

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3. You lead with generic greetings

women who lead with generic greetings make men feel weird Charlotte May | Pexels

Don’t start a texting chain with “What’s up?” You end up sounding unimaginative and just like everybody else.

Push yourself to come up with something different or interesting. With online dating, you can ask a question from something in his profile.   On the apps, be sure to look at all the photos of each guy — there may be one showing activity or a funny face he made that you can ask about.

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4. Your questions are uninspired

women who ask questions that are uninspired make men feel weird MART PRODUCTION | Pexels

If you want to have fun exchanges, don’t talk about work. You can ask, but don’t start there or linger long. Get to more fun topics like what’s his favorite food or pizza, or what is he watching on TV.

What does he like to read? What’s his favorite movie or the last movie he saw? What kind of music does he listen to? Ask about his hobbies or how he spends his free time. These are texts that can start a conversation!

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5. You don't let your sense of humor shine

women who don't lend their sense of humor shine make men feel weird Laura Tancredi | Pexels

Please lighten up and stop being so serious. Even though everyone might not be funny, a good sense of humor goes a long way with texting. 

If you can be clever or quick-witted, use that to your advantage. When you are entertaining, he’ll naturally want to know more about you.

RELATED: 8 Ways To Be Incredibly Charming Over Text, And 8 Mistakes To Avoid At All Costs

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6. You ask awkward questions that prompt awkward answers (or none at all)

women who ask awkward questions make men feel weird Photo By: Kaboompics.com | Pexels

Do not ask him about his weekend plans. If he's got plans with other women, either he’ll be vague or things could become awkward. Neither of you is interested in hearing him explain what he’s doing on dates with other women.

A 2020 survey by the Pew Research Center suggests that men often feel uncomfortable when asked overly personal or intrusive questions on dates, particularly early in the relationship. This can make them feel vulnerable and put on the spot, potentially leading to awkwardness and a perception of a lack of respect for personal boundaries. Societal expectations of masculinity can amplify this discomfort, which may discourage open sharing on specific topics. 

RELATED: 7 Signs Of Toxic Texting + Examples Of Toxic Texts You Do Not Want To Send

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7. You use the same opening line on every single man

women who use the same opening line on every man make men feel weird Sam Lion | Pexels

There is no “one size fits all” texting solution. Be creative, and whenever possible, tailor your message to something specific about the man who caught your attention. This is how you’ll stand out from other women he may be texting or has been texting in the past. 

2015 research suggests that in the early stages of a relationship, good texting between a new couple involves maintaining a positive tone, being responsive, initiating conversation, aligning texting styles with your partner, and focusing on expressing interest and affection while avoiding overly demanding or negative messages. Essentially, they mirror each other's communication pace and create a sense of connection through thoughtful texts.

Here are some tips for good texting:

  • Try a compliment. You can mention eyes, biceps, or clothing to stay in the safe zone. A little flattery is fun and flirty.
  • Comment or ask a question about a photo showing an activity. That’s a great way to get a conversation going because you’ll be asking about something he enjoys.
  • If he is a Baby Boomer, you can always fall back on classic choices. For example “Coke or Pepsi?” “Beatles or Rolling Stones?” “Deep dish or NY-style pizza?” “Mountains or Ocean?”
  • Teasing is an old high school flirting trick that works at any age. You can always respond with something like, “Aw, I bet you say that to all the women.” Or “Stop making me think about you, I’m busy.” Use emoticons when teasing like a wink so he knows you’re kidding.
  • Keep it short for the best chance of getting a response.

Stop texting when the man makes no effort! Last but not least, if you’re texting with a guy who responds with one-word answers and never asks any questions, recognize that’s a sign.

He’s letting you know he’s not into you or he’s lazy. Either way, why keep texting him? Many of my clients want to know how to keep the texting going, but I don’t advise that.

The only reason you’re texting is that you hope to meet him and go on a date. After a few exchanges, drop a guy who doesn’t make any effort.

After seven days, if he hasn't asked to meet, you can ask him. If he puts you off or makes excuses, block him and move on if you are serious about finding love.

Why waste time texting a man who isn’t hot to meet you? Getting to the face-to-face date is what you are after — and what you deserve!

RELATED: If You Text A Guy Like This, He Probably Won't Take You Seriously

Ronnie Ann Ryan is an Intuitive Coach, Past Life Reader, and author of six books. She’s the creator of the free audio course How to Ask the Universe for a Sign and Get an Answer Within 24 Hours. She's been published on ABC, BBC, and NPR.

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