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About me

I am a 16-year-old introverted boy and rarely talk to girls (if ever). I like math, awkward in any conversation 90% of the time, am Asian, not very good-looking.

Story

I go to the school library alone to do maths as usual and I used to walk past the same girl frequently. Then, I eventually started to like her.

She appears to be an introvert, likes reading (I think), a grade younger than me (year 10), respectful towards friends (i.e. stops what she's doing and gives her attention), she feels comfortable with her friends (ie.. does cute love hand gestures and quick dances), usually hangs out alone (from observation).

My problems

How can I approach/start a conversation with her? I just wanted to get to know her and develop our relationship from there. Maybe teach me how to maintain a conversation?

I'm asking because today I lost my greatest opportunity (i.e. library not crowded, she's alone, my friends are not present). I thought of saying (but didn't):

Hey, I know this is really really random, but um I saw you sitting here and I thought you are really cute and I just wanted to say hi. I am John.

  • 2
    How do you actually know she is introverted or geeky? Would your approach be different if she was one or neither of these things? – user8671 Feb 21 at 15:18
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Your approach might work if she has noticed you and is also interested in you. However, if she hasn't noticed you or she's noticed and isn't interested, then such a blunt approach is likely to make her uncomfortable, which will translate into her not wanting to continue the conversation.

What to do instead

A better way to approach is to find a less blunt conversation starter. Instead of just blurting out that you like her or that you think she's cute, start talking about something that she is interested in, such as the book she's reading, or another book from the same author, the music group/TV shows on the tee-shirt she wears, or the small dance she made. For example, if she was reading a book by an author you knew then you could say something like this.

Hey, I noticed you're reading [INSERT_BOOK_TITLE]. I think she's a fantastic author. How are you enjoying it so far?

You said in a comment that you don't read much and thus will be unlikely to know the books she has. That is perfectly fine. The important skill here is to make an observation about her that you can translate into a conversation that you know she will have some level of interest in.

What this accomplishes

I have a lot of experience (8 years of dating, 4 years as a professional consultant) with meeting new people and starting conversations. I've found that this is the best approach because it creates an active conversation for both parties. When you are attempting to meet someone that you like, it is especially important that they be actively engaged in the conversation, because if they aren't they'll likely get bored and move on.

This approach will be a lot more comfortable for her than simply walking up and telling her that you like her. Having someone that you've never met come up and express interest in you will take many people by surprise which instantly starts the conversation off at an imbalance (she'll be on her back foot so to speak because you've forced a romantic context into the conversation despite having never talked to her before). By starting with a neutral topic of conversation instead, there won't be an imbalance and she can be more relaxed and comfortable in the conversation.

This approach also has the added benefit of giving her the option to comfortably back out. As you converse, if she's not interested in continuing to talk, she can more easily end the conversation. My fiancee (also an introvert) has confirmed that it's much more comfortable to end a casual conversation than to turn down someone expressing interest.

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    If you don't have great book knowledge, you could try the other suggestions in the post (if her shirt has something interesting on it like a band or a movie, the dance that you mentioned seeing, etc.) The main point is to observe her, and pick a conversation starter based on something that you observe. I wouldn't offer to help with her books as a first conversation, unless she's very obviously struggling with them. – Rainbacon Feb 22 at 3:07
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    Just in case it doesn't go without saying, don't claim to like an author you're not familiar with, or one that you've recently made negative comments about where she could hear you or online. Recovering from being caught making objectively false claims is much harder than talking to someone new. People generally do not like being lied to, and there's no need to - there will be something you can talk about honestly with her. – Ed Grimm Feb 23 at 3:26
  • @EdGrimm Right thanks – Fred Weasley Feb 26 at 1:48

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