I need some help/advice UPDATED

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I added this girl as a friend on Facebook. I would like to eventually ask her out, but I don't want it to be the first thing I say to her.
I would like to start with a nice hello and some small talk.

The only reason I know her is because she my friend's ex-girlfriend's sister. My friend and her sister were planning on getting married but broke up and then like two months later she married another guy.
I don't know if she even remembers me. I met her a few times a couple of years ago. I know her and her sister both have some really big emotional issues. She's pretty reserved and quiet, plus I don't think she has that many friends. I think that's why I want ask her out, because we both have our problems. I also know that her family is pretty conservative and she's not "easy", which is what I'm looking for. I am also a bit hesitant to do it because she's 18 and I'm 22. I don't really have a problem with it, but I know others might.
Any tips or advice would be really helpful

Last edited by werkinit on 19 Jan 2010, 11:12 pm, edited 2 times in total.

Prehaps, she is reserved and quiet and doesn't have many friends because she does have big emotional issues as you state.
Are you prepared to handle such big emotional issues in additional to what your problems may be?

Her family is conservative and "she is not easy"...so, it appears Mom and Dad have instilled a good value system in her. There is nothing wrong with having a high sense of moral and personal values.

As for her being age 18 and you are age 22, why would others have a problem with that? Most married couples today are similiar in age, the male being at least two years older than the female and oftentimes older. Why the actress, Demi Moore is in her mid-forties and married to Ashton Kutcher who is, probably, in his early 30s now. Age is just a number. Don't let that hold you back.

If you want to get to know this girl, send her an message on Facebook to "break the ice." Ask her about her likes and dislikes,
what things interest her. Ask her if she remembers you when you met her a couple of years ago. Once you get to know her a little better, ask her if she would like to meet you at the local MacDonalds (or someplace similiar) for coffee...

Just don't scare her off...have patience and take it slow.

Best of luck to you!

^ jupp, this.

(Don't stress her in any way, and if she has some emotional issues she might get frustrated if one shoots off 100 questions from the start. Other than that just be kind and funny, you can't go wrong with a little humor.)

Chat her up. Basically express a lot of interest in her and what she does. What is she doing these days? How is it going? What are her plans for college? Is she working, if so, what is she doing?

Once you get a decent rapport going, you can ask her questions about you like "does this picture make me look fat?"

After a few exchanges, ask her out for a date - but don't phrase it as a date. "Have you seen ...? Lets go on Friday!"

If that goes well, ask her out on a date. "Hey, I had a great time, would you like to go on a "date"? I have an idea of ..."

So i sent her a message pretty much saying hey whats up and she responded with stuff about school and work and what am I up to. But after I reply to that and ask her about school/work, what do I say? I suck at this stuff! and would really like to get to know her.
And how long 'til I ask her if she wants to hang out? I think she probably knows me intentions

Heh, no one's perfect at this stuff, all we can try to do is give you ideas

"Wow, that sounds interesting, what is _____ like?"
"Hey, I heard that's tough, is ____ really difficult to do/learn?"

Basically the idea is to make what she does sound entertaining and upbeat. You don't want to make it a downer to talk about things she's interested in and you want to express an interest in the things she does. Now if you follow the PUA guidelines, you'd throw in a few 'negs' about her and/or what she does. I personally think it's BS but hey, whatever floats your boat.

she seems to be at least mildly interested in me now. ( more than I thought she would) I really want to ask her to do something with her now. But I'm afraid that if ask her and she doesn't want to go out even as a friend, she won't want to talk to me anymore. She's real nice and I really like talking to her. I just like having someone different to talk to. But I'm also worried she's only trying to be nice
I hate how damn difficult it is for me to talk to people.

Hi it's useful information.