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To establish the background of the story, let me explain who is the flirt and what is the relationship between each other in my case.

I'm a 23 years old male and my flirt is also 23 years old but a female. Me and she are both open-minded about anything and we are funny. We always make jokes about sex, but we never done that.

So, we went the same highschool but had never talked back then. But last summer, I texted her somehow and we started chatting. After a while, we decided to meet. The meeting was pretty good actually since we are both selective when it comes to communication. After two or three meetings, we stopped talking because I'm a person who waits the initiation from opposite party. It seems like she is too...

Now the question part: Today we have started chatting again but the interesting part is we were being childish and funny again. But at the end the conversation went like this(I don't know any way to improve visual on this conversation if any, sorry):

She: I thought you were irritated because of me and because of this I also got irritated by you :D
Me: Wow, actually I didn't even think anything like that, why didn't you share that with me at least?
She: Do we need to tell this to other party in these kind of conversations, lol.
Me: Okey. (Me being on standby mode, waiting her to share her actual feelings, didn't work as you can see)
She: Okey...

What should I say in such situation to make her open her feelings? I know she is into me but I don't know the key or whatsoever. Conversations like this have occured to me way too much and I felt like I need to ask you about this.

closed as too broad by apaul, AndreiROM, Tycho's Nose, Catija Jan 19 '18 at 15:16

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

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She: Do we need to tell this to other party in these kind of conversations, lol.     
Me: Okey.
She: Okey...

What you did was to just accept what she said instead of asking a followup-question as you should have done. Something along the lines

No we don't have to, but I would like to know. So would you mind sharing that with me?

will continue the conversation. In case she doesn't want to tell you, you could continue the conversation by asking for the reason.

Yes it's all theoretical and hard to predict how it will keep going, but I hope it gives you an idea what you did wrong and how you could improve it.

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    Thank you! I will give this a try :) – HalilM Jan 19 '18 at 15:04
  • maybe you should wait for a few other approaches as well as comments. it might not be the best idea, but surely something you could try. (there might be better ideas out there. don't rush this) – XtremeBaumer Jan 19 '18 at 15:05
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What should I say in such situation to make her open her feelings? I know she is into me but I don't know the key or whatsoever.

In order to answer this thoroughly, we need to break it down in several points.

Let's start from that single specific conversation that undeniably left you both hanging. In order to unblock those types of hanging, even and especially considering that you two are funny prone-to-jokes people, I'd go with a

° ° ° Ping ° ° ° [smiling upside-down emoticon here] Your silence usually scares me. [big open-mouthed smile emoticon here] Alright, so, sorry for being awkward... [close-mouthed blushing smile here]

...after this "unblocking" line, try to IMMEDIATELY move out of the awkward zone with something along the line of

If you're not s_itting your pants, I'd like to go watch "The midnight man" at the movies tonight.

This is just a silly example. Use basically ANY activity you can suggest in a funny way in order to get out of the previous awkward situation and at the same time spend time with her.

Alright, so, done with the unblocking an awkward situation.

On the slightly longer run, as you know/suspect that she's into you on some levels, just go ahead and be straightforward (and, as always, funny), tell her in person. You seem to go along well so there should not be problems raising the issue, for example, with a

So, lissen, lemme do something I apparently can do pretty well, like making things awkward. I wanna tell you something... and I wanna tell you straight: what about us? Are we into each other? This has been milling around my mind for a while now.

Once your feelings toward each other are clear, everything will be easier imo.

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