Am I scaring away shy girls? How can I tell if they are just shy?

[Jayce]

So this is a recent but I think ongoing problem that I've encountered. Last friday at another party I went to, I met a woman ( I've never met her before so it was a completely cold approach by me). Anyway we were talking but unfortunately she dosen't give me much material to work with. E.g Me: since its holidays and all, got any travelling ambitions? Her: I'm just working a lot.

Maybe she was not interested in me. But I noticed that throughout the night she only talked a little bit to her other friend who she knew (and it wasn't much). I noticed she made a couple of glances at me when I was meeting other strangers. I noticed the "stand at the corner of the party". I asked her if she knew anybody else at the party. Like me, she told me she only knew exactly three other people there. She didn't really go out of her way to go talk to strangers either. So there are all these signs pointing to that there is a decent possibility she was shy. What are the distinct differences between shy and uninterested anyway? I find that there is a lot of overlap.

Being a formely/ still sometimes shy person myself, I'm not good at pulling people out of their shells, and I'm not particularly good at directing/ controlling conversations. I've always socialised better with people when the conversation goes both ways. Shy people usually take up the listening role a lot, in my personal experience. I don't mind all this I just wished I could be more skilled in helping shy people I don't know feel more comfortable around me.
Any advice?

The few solutions I've comed up with and am willing to experiment:
Tell her " Um I'm kind of shy, but I want to tell you that I like you."
Improve conversation management skills. I'm already onto it.



Also maybe this is a false hunch, but I might be scary to shy women? Not as in creepy scary, but I make them feel nervous scary? I've never brought this up because me making a woman feel nervous cause I'm really attractive? That sounds way too good to be true. But there is some evidence pointing to this. Last Wednesday a woman walked up to me and kind of tried to mumble something. I thought she was trying to sell me something so I said oh I'm not interested in buying anything" smile, and I walked away cause I was going somewhere. As I was walking away already, her friend then shouts "she thought you were cute!". Last year when I first started to learn how to approach, I told a woman "Hey I think you're pretty". She said thanks and hid behind her book a bit. Today after my first game of dungeons and dragons I asked the woman in my party what her name was, since she was a regular player and I'll probably see her around. She squeaked to me with a mumble "It's a mystery". Three months ago I was talking to this new female co worker, getting to know her to see if I might want to date them (I don't think saying to her "I like your choice of purple colour for your clothes" counts as flirting. It did catch her offguard a but though. After work I was walking up to her to make more conversation and she just walks out the door. The other co worker who was school friends with her, told me she was shy after I asked him "is she usually a quiet person? She seems so".

Oh yeah forgot about this, during my time playing D&D today, she didn't talk much and had a very soft voice that was almost hard to hear. And the neutral looking clothes as well as not much eye contact. She definitely pings as stereotypically shy.

At the same party I was at, after my friend introduced me to his friend and told him we met in dance class, the guy's first words to me were "you look like a good dancer". Ok yes I am going for the overly assertive and trendy, conventionally fashionable look. Glad to know its working . But I'm not extremely conventionally attractive on most days if not all days, even when I do my hair and makeup, I still fall short of being on GQ magazine anytime soon. Nor do I ooze charisma all the time. I'm just willing to go out my comfort zone more often. So I'm probably not intimidating to shy women. I doubt anyone is going to look at me and think he's out of my league or whatever.

Making super warm approaches is not really possible since all the woman I meet these days are people I've never met before. The best I can do is a lukewarm approach.

[Caffeinated]

With shy people it can be really hard to tell how much of a lack of response is shyness and how much is wanting not to talk/interact with someone any more. I like your idea of straight up mentioning that you're a bit shy but want to tell her you like her.

If you're dressing in a trendy and fashionable way and meeting people in generally nerdier circles, you could indeed be intimidating them. Nerdy girls can have unpleasant histories of being bullied by the cool clique in high school, and if you ping on the radar as a cool clique type she might think you're looking to set her up for humiliation rather than actually liking her.

The response of the girl at the party about holiday plans reminds me of times when I've gone home after a social event and had the late night self-berating session where I can't believe I said something so lame, but got so tongue-tied in a conversation that I dropped the ball. If she's shy or socially awkward, she could be thinking exactly that and wondering why she couldn't have been smoother talking to you.

I'm also a little reminded of a recent Captain Awkward where there was a fascinating discussion in the comments about different conversational styles. Some people liked to ask questions and be asked questions in return, and other liked to tell anecdotes and be offered anecdotes in return, and both groups felt a little uncomfortable in conversation with the other. Here's the link: http://captainawkward.com/2014/11/24/648-on-dates-i-feel-like-i-am-making-all-the-conversational-efforts/

In light of that, maybe have a couple anecdotes to relate, in case that's her conversational style?

[eselle28]

You've described a few different situations, and I think some of them are best discussed separately:

- The woman at the party could have been shy, or could have been uninterested, or could have been having a bad night, or might just be unfriendly or a poor conversationalist. If she's given you that little to work with, does it really matter? I mean, what is there to like about her aside from her appearance? Sometimes you just have to let it go and not get too hung up on helping someone who may not even want to be helped.

- The woman who approached you was obviously interested but shy. The usual social script is that women invite or discourage approaches, men make them, and then women react to them. When things get flipped, both men and women are often pretty clumsy at playing the other gender's role because they don't have much practice at it. You can't necessarily make women more adept at approaching, but being more open to the possibility that they might be doing that rather than trying to sell something could take some of the tension out of the situation. If you could press the rewind button on that interaction and had some interest in the woman approaching, something basic like, "Hey there, I'm Jayce," might have kept the conversation going after the awkward mumbling bit.

- With your coworker and the woman with the book, you started the interaction with visual compliments. I'd strongly advise against this. They can be really awkward to respond to. I mean, what do you say in reply to a stranger telling you you're pretty beyond thanking him? Compliments from coworkers you don't know well can be awkward as well. Rather than starting out that way, I would instead suggest that you ask questions or make small talk about neutral topics. It might also help if you focus on context. A woman who's reading may very well not want to talk to anyone, let alone a stranger who thinks she's attractive, and a coworker who's on her way home might not want to stop and chat because she has things she needs to hurry off to do. I'd suggest directing your approaches in public to women who aren't engrossed in something and to make small talk with coworkers during relaxed times at work rather than at times when people might be heading off somewhere.

- The woman at your D&D group doesn't want to interact with you. Even shy people can tell others their names. I'd suggest leaving her alone as much as possible.

[Jayce]

You've described a few different situations, and I think some of them are best discussed separately:

- The woman at the party could have been shy, or could have been uninterested, or could have been having a bad night, or might just be unfriendly or a poor conversationalist. If she's given you that little to work with, does it really matter? I mean, what is there to like about her aside from her appearance? Sometimes you just have to let it go and not get too hung up on helping someone who may not even want to be helped.

Well she did tell me about the music she liked, and why she really liked them and asked me what I liked. And she expressed her love for boy bands and her interest in different cultures. The conversation just kept dying though cause I'm still not 100% used to being the dominant speaker, while having the other person listening most of the time. There was a brief time where the conversation died and she was just looking at me directly. I think it was a queue for me to start a new topic. But I couldn't think of anything so I just excused myself and went to meet other people. So there is a chance we kind of were getting somewhere, and maybe we were at least mutually interested in talking to each other a little bit. But the whole her listening and waiting for me to make every move, put me in a position I'm not particularly experienced with. It's kind of like being expected to be the dungeon master, you would totally love to be the dungeon master, but you've never been the dungeon master before, and you're not even familiar with all the rules of the game yet.

She also personally, came up to me and kind of did some kind of "hey, I'm heading off, bye" gesture to me when she left. Good news though,the party I was at is a recurring event that gets hold every two months or something, and she told me that she goes to this event frequently. And the community is also quite small, I might bump into her again.

- With your coworker and the woman with the book, you started the interaction with visual compliments. I'd strongly advise against this. They can be really awkward to respond to. I mean, what do you say in reply to a stranger telling you you're pretty beyond thanking him? Compliments from coworkers you don't know well can be awkward as well. Rather than starting out that way, I would instead suggest that you ask questions or make small talk about neutral topics. It might also help if you focus on context. A woman who's reading may very well not want to talk to anyone, let alone a stranger who thinks she's attractive, and a coworker who's on her way home might not want to stop and chat because she has things she needs to hurry off to do. I'd suggest directing your approaches in public to women who aren't engrossed in something and to make small talk with coworkers during relaxed times at work rather than at times when people might be heading off somewhere.

Well I don't approach people in public venues where people aren't expected to interact,  cause I don't like it, not really what I want to do, and its also extremely ineffective, that situation was all the way from last year where I only started to learn how dating actually worked. So I tried all sorts of strategies. But you are right, in the book situation I did start with the visual compliment which is hard to respond to. But in the co-worker situation I didn't start with a compliment, I actually started with "hey I can't believe we both went to the same high school, but we've never met!". And we talked about many things before I made her feel a bit caught off guard/uncomfortable with me noticing her wearing a lot of purple colours.

- The woman at your D&D group doesn't want to interact with you. Even shy people can tell others their names. I'd suggest leaving her alone as much as possible.

Definitely.

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