He’s definitely not shy, and it looks like he’s always flirting with me when we are together. I feel a strong chemistry and connection, we have a lot in common and our discussions are always great in person. He makes a lot of eye contact, he’s always smiling, and even though I’m very very shy I slowly started to find the courage to reciprocate this behaviour (and it’s pretty clear that I do that only with him and not with other friends of us).
It’s well known that I’m very shy and cold, but I’m different with him and everyone notices that.
He complimented me about my look, he always makes jokes about things I’ve said in the past, and other things.

He was the first to ask for my contacts, but I decided to text him first to demonstrate my interest. He wasn’t a fast replier (I got something like a reply a day), so I didn’t continue the chat.
That happened some other times: I always started the chat but he wasn’t engaged.
Since we meet barely two days a week (and we have little time to talk in those days), I’d like to hang out with him or at least text with him (we have beautiful discussions in person), but I’m really shy to ask, also because we are always surrounded by our friends in person.

I don’t get if I misinterpretate his behaviour… we have a very strong chemistry and it’s pretty evident. I’m very shy but it’s clear that I like him (I’m cold with everyone but I’m always smiling and blushing with him). If my interest is so obvious, why doesn’t he ask me out? And why does he never initiate texting? I’m too anxious to ask him… if he texted me I would try to ask him to hang out, but since he doesn’t I think that he’s just polite and that he’s not into me.

I just can’t explicitly ask him to be clear… what can I do? I feel pathetic about initiating texting with him again, but I really feel the need to take a step because I feel good with him and I really want to talk with him since we always have great conversations. What do you think?

3 comments
  1. Ask him out in person or over texts. I know you feel “pathetic” doing that but if you want to move forward you have to take the initiative. Stop trying to assume what he thinks of you based on subtle hints and behaviour. No way people on the internet who have never met him are going to know. He could like you or not and the only way to be sure is to ask.

    Or you could keep waiting until another woman takes the initiaitive and then all you will have is regret.

  2. I know you say you “can’t just explicitly ask him to be clear”, but that’s really the best way to way to get your answer. If you can’t muster up the courage to do that, I would expect to keep having to guess and wonder. And which is worse: the one time anxiety of asking one question, or the ongoing anxiety of never knowing?

    You say that it’s clear that you like him, but as a man let me clue you in on something: by and large, we’re oblivious idiots. It might be clear to *you*, and even to your friends group, but that doesn’t mean it’s clear to *him*.

    I would suggest a simple, non-threatening question (feel free to text it if face to face is too overwhelming) something like this: “Hey (person), I’ve noticed (behaviors you wonder about), but I’m kind of shy and unsure if that’s just you being friendly or if you’re flirting with me. I feel like we may have chemistry and was wondering if you’d be open to (casual date idea that fits your vibe – coffee or lunch or whatever) to talk more one-on-one and see if we click.”

    As someone that had to learn how to do this after his divorce, I know very well how scary it can be, but once you do it a few times, you’ll realize that it actually isn’t so bad, and you will (usually) get the direct answer you need (even if it may not necessarily be the answer you *wanted*)

  3. I mean, high school girls are asking out guys these days, he probably assumes if you’re interested that you’d do something about it…since you’re an adult.

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