Initiating texts with shy guy?

Hi. I want to open up dialogue with a guy I like, but he's not much of a "chaser". I initiated a conversation with him on messenger 3 days ago, it went well and he ended by saying "I'll talk to you later on!" I don't want to throw myself at him so I'm going to see if he's interested enough to start a conversation with me.
But I know this guy isn't the reach-out type, and it's very likely that he just considered it a friendly chat and went about his business. I'm aware that I may need to initiate the conversation a few times before he'll be comfortable enough to randomly drop me a line, let alone ask him to hang out.

So basically, what would be a sensible, un-needy time to wait for him to initiate a conversation before dropping him another line, and how many times would I do that before determining that he's actually not interested instead of just being introverted?


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What Guys Said 2

  • Personally, it takes about 2-5 times of the girl reaching out to me before I get comfortable enough to actually start a convo myself. It obviously depends on the person and the conversations themselves, but in my experience, girls who initiate contact often have to do it at least once more unless I see something that 100% relates to what we've been talking about earlier.

    Honestly, 3 days is a lot so I'd consider starting another one soon. Shy guys are often pretty happy that girls initiate conversations with them. Just don't overdo it, like you said, neediness isn't that great.

  • A couple of days is fine and I would keep it up for about 2/3 weeks to see if any connection develops


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