How to keep an online conversation going - Hey Saturday (2024)

Today, I’m delighted to say that our blog has been hijacked by the very cool dating expert, Claudia Cox. She is the author of ‘French Seduction Made Easy‘ and is passionate about sharing her expertise on communicating well in relationships especially via flirty texting. She runs the website textweapon.comwhere she makes the art of seduction look easy peasy. If you haven’t already, head over there and check it out. Over to Claudia for some savvy advice on how to keep that online chat going in the right direction.

Keeping an online conversation going

So you’ve passed the awkward “first contact” stage of online dating. You sent the first message, they replied – congratulations, everyone is onboard and ready to roll!

So, what now?

It can be hard to keep a conversation going with someone you don’t know YET, and who isn’t sitting across the table from you. You want to come off as fun, interesting and flirty, while also being considered serious, smart and trustworthy, right?

Aie, aie, aie… That’s quite a big task to accomplish using just a few messages to and fro! And you know what makes it even harder? Is that you don’t know what makes them tick yet – or even if it’s worth finding out…

If you find yourself stuck one message in, and you want some advice on how to spark up an interesting conversation that will tell you whether this person is worth getting offline for, read on.

1. Ask questions

Pretty much everyone loves talking about “numero uno” – so give your partner an opportunity to start gabbing away! Asking light, simple questions is a sure fire way to keep a conversation going online. The more they answer, the more fuel you’ve got for the conversation. Even better, you’ve just won some major points by flattering their ego (even if it’s just a little).

It’s also a good indicator for knowing if you have found a worthwhile match or not. “How so” you say? Well, if after asking them a mountain of questions, they still haven’t asked you the basics, you can be pretty darn sure they are self absorbed, and not the least bit interested in finding out what you’re all about. Time to move on, nothing to see here folks!

Keep it fun, it’s not a job interview – make your question a little quirky and different. This way you stand out from the rest of the “fishies” and get a better reaction – and please, don’t ask something they’ve already answered on their profile.

2. Get your flirt on

Flirting is fun, but when you’re doing it online you need to be slower about it than normal. Because your partner can’t see you, or the signals you’re sending, flirting too early in an online exchange can be a huge turn-off. Don’t immediately start talking about adult toys or send her a “selfie” at the gym all pumped up post workout. Make sure that you add just a lick of sass to your pre-meet up messages.

Going back to the good old questions, instead of asking him or her something dull such as “what did you eat for lunch?” give your questions a hint of spice. Ask “Why are you a cat person when everyone knows that dog people make better lovers?” Or poke fun at their answers in a flirty way (“Oh, you’re a Star Wars fan? Bet you’ve got Darth Vader pillowcases J”).

Make sure you don’t go overboard. Nothing kills a conversation early on like pushing boundaries waaaay too far (like being outright mean or vulgar).

3. Be honest

When you’re messaging almost anonymously, it can be easy to exaggerate or outright lie to make yourself look better. Don’t do it! One, because it will get awkward if you ever do meet up, and two, it’s human (and often endearing) to have flaws – embrace them, and your partner will too.

If you’re not proud of your height, say, “I’m short, but what I lack in height, I make up for in over-confidence.”

Make your flaws into a joke that you can both laugh about – they’ll be more likely to share theirs, so you don’t get any special surprises when you end up meeting.

4. Know when to take it off (line)

Even if you’re enjoying the online messages, don’t push your luck. Know when to take your virtual relationship offline before it fizzles out. After all, dating is about meeting up face-to-face, hearing their voice, drinking in their smell and feeling their touch.

In my experience, it’s best to meet up earlier rather than later – like before you know everything about each other, and you still both have an air of mystery about you. After all, you want your first date to feel like a first date, not a 10th wedding anniversary, right?

Online conversation debrief:

Before jumping straight into it with the great advice you’ve just received, commit to memory the following “do’s and don’ts” of online conversation:

For the ladies:

Don’t be negative. Opening up with “I’m so sick of online dating…” makes you seem unenthusiastic… and also like you’ve been doing this for way too long.

Do be complimentary about his photo. Don’t make any jokes about it being photo shopped, the male ego is an extremely sensitive thing!

For the Gents:

Don’t go there. Seriously, men are the worst offenders here – don’t talk about the size of ANYTHING until you at least know what her favorite drink is (and have bought her a few)!

Do keep it light and fun. Don’t write long essays about yourself, which seem extremely interesting to you, but might not be all that easy to reply to. Stick with light, flirty topics that keep engagement levels high.

Well, there you go! 4 tips for keeping the online conversation going like a champ until you meet up in the flesh. Happy online dating!

How to keep an online conversation going - Hey Saturday (2024)
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