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How do I approach a shy guy and ask him out?

Tagged as: Crushes, Dating, Friends, Health, Trust issues<< Previous question   Next question >>
Question - (11 May 2015) 2 Answers - (Newest, 30 June 2015)
A female United States age 30-35, anonymous writes:

Dear Cupid

I broke up from a very long relationship few months back.

My ex is a very confident person which attracted me to him in the first place, but he is so confident that he can get any girl he wants, he treats me like shit all the time, ridicules me and I never got that secured feeling from him.

He always made me anxious, scared that he is gonna leave me.

I was in a very bad place and few of my good friends and my sister made me see how horrible he is treating me, long story short, I broke up and he never really cared and I'm kind of over him now, though I think about all good things we had time to time.

Due to my anxiety and self esteem issues I'm attending kind of a social meet up group, it is going well and I like there.

So I met a guy there, he is younger to me but I'm attracted to him, he is very shy and doesn't make eye contact and never really talks to me, he is totally opposite to my ex which I guess attracted me to him.

So how do I approach him, I don't want to come out as desperate and needy, I never really dated a shy introvert guys before.

I used to go out guys like my ex, the overconfident macho guys. Pls help me

View related questions: broke up, my ex, self esteem, shy

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A reader, anonymous, writes (30 June 2015):

nice, awesome to hear of a woman interesting in asking out a man for once.

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A male reader, WiseOwlE United States + , writes (11 May 2015):

First of all, I don't think you've had enough time in recovery and healing to be dealing with anyone in a romantic way.

You are feeling attraction out of rebound feelings. You just came out of a traumatic experience. You ARE in-fact, desperate and needy. Considering what you've been though.

Your attraction may be for someone who may be emotionally-fragile, and he just so happens to be within your recovery group. Sorry, but your issues with self-esteem and anxiety will not make you ready for dating just yet. You should be concentrating on these issues, not searching for someone to subject to your emotional problems which are a work in progress. Concentrate on healing and getting better first.

This isn't a good place or time for you, or for the person you're attracted to. It may be convenient that he's in close-proximity and visually available; but if he is shy, it may not be good to make him feel stressed or pressured in a place where he is seeking his healing. Feel free to be friendly and test his reaction to it. If he seems distant or withdrawn, leave him alone. He's not there searching for dating opportunities, he has issues to deal with.

Many support-groups have rules and guidelines about personal interaction between participants. Some groups discourage "dating" or making advances towards members who are under treatment and counseling. I think these are boundaries that are necessary, so members and participants can feel at ease; and not pressured by others with more outgoing personalities. If he hardly talks, there is a reason; and he's working on it.

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