Just the Tips

How to Keep the Online Conversation Going

Woman Using Laptop on Bed

How would you rate your conversational skills with women? Are there usually long awkward silences? Are you unsure how to begin a dialogue?

When you meet women online, there is usually a week or so (maybe less, maybe much longer) where a woman will want to suss you out, make sure she feels comfortable and safe enough to meet you in person for a date or a hookup.

Beyond safety she also wants to know if there is a spark, enough chemistry to make it worth her while. And yes, you are likely trying to figure this out too. These back-and-forth messages often take place through a dating site, texting on your phone, or social media DMs.

If in-person conversations with women make you sweat, you may also have issues online. But sending messages through your computer or phone can be easier—she won’t see you sweating, your hands trembling, or that you need a good shave.

If you are genuinely interested in a trans woman you’ve met online, but your conversational skills suck, she probably won’t take you seriously. Let me share some tips that help to hold a woman’s attention and interest.

How to Keep the Online Conversation Going

Give her something to work with in your profile.

If there’s even going to be a conversation, you want to have a decent profile for her to relate to. It’s all she has to go on until she actually meets you, and if it’s just a couple of lines and one bathroom selfie, you can be sure things won’t go far.

Put the effort in to create a stand-out profile, and you might even get more first messages from women.

Start off on the right foot.

Truth is, men do send more first messages. But most of them suck and don’t even get a response. I can’t count how many boring, generic messages I’ve had over the years: “Sup?” or “How was your weekend?” or “Hi, beautiful!” Blech—nothing creative or thoughtful to pique any woman’s interest.

Read her entire profile and comment on something in it. For example: “I see you enjoy creative writing, have you taken any classes? What genre do you like to write in?”

Don’t be afraid to flirt, but keep it nonsexual.

Flirting online is challenging, especially if you haven’t met in person. Until you feel the conversation has become playful in tone, keep things chill and stay away from pet names, like “Honey” or “Sweetie.” Even if she’s the hottest trans woman you’ve ever encountered, you don’t need to focus on her looks—she knows she’s hot, believe me.

You can mention her appearance without being overt: “You look stunning in that picture by the waterfall. Where was that taken?”

Ask the right kind of questions.

I’ve engaged with many men on dating sites where the conversation is a one-way street that turns into a dead end. How? I keep asking questions that a man answers with a one-word response or a short phrase, without any questions back. This is tiresome and sends the message that you aren’t that interested. This one-way convo never lasts long.

Think of and ask her things that require more than just a “yes” or “no” response. She may be challenged about conversing online too, and if so, one of you needs to take the lead.

If you’re stuck, try changing the subject.

Until you know someone’s texting ability and style—keeping a bouncy conversation going for an hour, not answering for a day or two, preferring to talk on the phone or through video chat, using lots of emojis to express themselves—it will be hard to interpret subtleties.

Keep things easy going by asking about what she’s already revealed in her profile or in messaging thus far. If you’ve crossed a line you didn’t know was there, switch subjects quickly and apologize if necessary.

If you can keep her attention and interest, and make her feel comfortable, you may very well create the spark needed to garner that all-important first date.

How do you find communicating with women online before meeting? Is it challenging? Please share in the comments!

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