Let’s Keep Things Interesting – How To Avoid Boring Your New Online Match by Frequent Dater

Dating blogger Frequent Dater provides his advice on how to keep things interesting while chatting to your new online dating match. 

Online dating is great isn’t it? On the whole anyway. I mean, what’s not to like about browsing, almost anonymously, at the opposite sex’s dating profiles and fiercely judging them as you go? Whilst this is great fun, and we all do it (yes, you as well if you’re honest), what happens when the mild-stalking turns into attraction and you pluck up the courage to get in touch? What then? You can’t hide forever and now you’ve made your lurking public you have to dive in with both feet.

But how?

Conversing online has its benefits and you should definitely use them to your advantage. How often do you meet someone in the bar and instantly have access to a raft of photographs showing you what they get up to in their spare time and where they took their last holiday? Not only that but how long would it take in “real life” to find out their favourite music and what they like to eat without simply blurting those specific questions out over a drink?

You see, the key to successfully traversing the online dating world is to make note of your surroundings, or in this case, your new interest’s online dating profile. Most people, and I mean most people that want any degree of success in their online dating pursuits, will fill out at least the basic personal information in their profile. If you’re really lucky, you’ll have their life story to digest and thing of witty questions from. And that is the key to striking up and maintaining great conversations online, look at what they’re into or they’ve done and use that as the core of your conversation topics.

Take these examples for instance;

If their photos show them on holiday somewhere… “That photo of you on the beach is amazing, where did you go?”

If you can see they have a pet… “Does having a <insert animal here> bag you more online matches?”

If they’re on a night out with friends… “What’s your favourite club in ______ (the area they’re from)?”

If they look particularly nice in a photo… “You look lovely in the photo where you are in the <insert outfit here>”

Hopefully you noticed the theme; find something that represents them and build a conversation around it. Not only does it show that you’re paying attention, it also displays your willingness to find out more about them. Keeping conversation on them will make things easier for you if you’re not particularly good at talking about yourself. I would however, encourage you to turn some of the above round to you and your experiences, for example;

“Is that a photo of Venice? I went there in 2015! How did you find it? What was the best thing about the trip?”

“Is that your <insert animal here>? I have one too, aren’t they great? What’s your pet’s name? Mine is <insert name here>.”

Ok, you get the point. Ask them about themselves, starting with what you know based on the information available to you and then conversation will naturally move towards other topics where you can get to know each other more.

If for any reason the conversation dries up at any stage, I always like to have a few random questions to throw into the mix, mainly for a bit of fun but also to reignite a dying chat!

“What three things would you take with you on a desert island and why?”

“What would you do if you won the lottery?”

“Do you have a party trick?”

“What’s the weirdest thing you’ve ever eaten?”

None of the above are very serious so it’ll lighten the mood when you’re both struggling with things to say. They also work well as 1st date ice breakers so make note!

Hopefully you feel more confident about striking up that conversation now, go ahead, what are you waiting for?!

If you want to hear what women want from their first interactions online then head on over to my recent post here (link to www.thefrequentdater.com/best-tinder-openers) where I asked a fellow blogger to tell me her thoughts on the matter.

About the Author

Mark is a 31-year-old singleton and dating blogger over at www.thefrequentdater.com where he covers a whole host of subjects ranging from great date ideas to knowing how many dates to wait before sleeping with your date. Why not head over and check out his blogger or follow him on Twitter (@frequentdater).


2 Comments Add yours

  1. revengestar says:

    that applies if the person is relatively inexperienced. For people like me who use online dating for quite some time now, we made those questions when we were 22.


    1. Thanks for your comment! We will pass your feedback on to Frequent Dater, our guest blogger on this post. We like to make sure we cover all levels of dating experience and this post was in response to another members comment. We will look to get some content up for the more experienced online daters soon – keep a look a look out for it! Thanks again for your interest in this post.

      Liked by 1 person

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