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Should I ask her out? Flirt?

Tagged as: Dating, Friends<< Previous question   Next question >>
Question - (17 March 2009) 2 Answers - (Newest, 19 March 2009)
A male Canada age 30-35, anonymous writes:

There's this girl that I like. She's one of the nicest person you can meet; she's a little shy, but once you warm up to her, fun to be around. Another thing is she had been extremely sheltered through out her life, so at times she seems a bit innocent. Somehow, I got close to her; probably through making the 'wrong moves'? I've given her a present for her birthday, treated her nicely, heck, even comforted her when she was sad.

In other words...I've never had much experience with women, so the first time I tried to get close to this girl I really liked, well, erm, I ended up in the friend zone. We're pretty close friends now, and I suspect that although she had mentioned (to others, not me) that she'd prefer to date friends, I'm not quite sure if she'd date me.

I'm generally a nice guy, which is probably why I ended up in this position in the first place. I've never really flirted with girls before, so I never really sent her any signals that I like her more than just a friend. I also like her as a friend; few people are as supporting and caring as her.

Another guy was flirting (teasing, etc) with her and she obviously flirted back (body language); they've been at it for a while now, and when I saw it it just broke my heart; I was depressed for small while (she noticed...'What's wrong? Why are you so sad?' lol...). A while back she got rejected by her crush, and I asked if she had someone else in mind and she said no. But I see them together, and they seem to have this chemistry going. The only bad point that I can think of about that guy is that he smokes (I found out quite accidentally and he tried to hide it from me...).

To help me manage and reflect on my feelings, I've decided I need to minimize (not cut off - that'd be impossible) my contact with her. After wards, I'll be off on a co-op/intern job for four months, so minimizing contact with her then is not too much of a problem. Sounds like I'm running away, but I need a little bit of time out before my emotions get better of me. I'm a very emotionally driven person, so I think this is the best course of action for me.

I've been debating whether or not to ask her out on a date...but how does one do it? Should I do it during the summer? I've been debating whether it's worth the risk or not to tell her about my feelings...but when is it appropriate to tell her? I've also been wondering, what exactly does it mean to flirt? How does one flirt with another?

Or would the four months of minimum contact be enough to 'reset' and start over again?

View related questions: crush, depressed, flirt, shy, smokes

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A reader, anonymous, writes (19 March 2009):

This is verified as being by the original poster of the question

first off, thanks for responding, it did give me some hope.

well the thing is...she's also put me into her 'family' (she does this with her close friends), and apparently i'm the brother of the family, while she and her friend are the sisters.

see the problem?

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A female reader, salvadda Canada +, writes (17 March 2009):

salvadda agony auntWow, I was quite intrigued by your letter. Honestly, it seems like you have done everything right. I don't believe you have made any wrong moves. Though when a girl has been sheltered, you're very right to assume that she can be a bit nieve. By the sounds of it, she is open to sugguestions. By this I mean maybe she can not read into you as you would like her too. She may very well only see you as a friend, a good friend. Which is a good thing, because from what I read you have already gained her trust in consoling her in her time of need. Also the fact that you did get her a gift for her birthday which shows that you gave her both caring and thoughtful feelings. Trust me she does know this. I assure you that she does remember it all, and was touched, both times.

I do sense by your letter that you suppress some restlessness over the fact that you might be a bit afraid to let her know how you feel about her. This is very understandable.

You have developed the closeness as a friend, which is a wonderful way to start a relationship. If possible at all can you ask her on casual date? I think it would be very good for both of you. By casual I mean something simple. Nothing that would come between your talking time, such as a movie, bar, ect. If you can find out what she likes other that the latter that would be very good for both of you. A walk in the mall, stop for a bite to eat. Maybe to the zoo, or a walking in the park. I know it might sound lame, but most girls such as this one you wrote about would enjoy this..believe me. I suggest these things only so you may both have time to talk, without distractions. To get close on a personal note. You sound like you are a very listner, and genuine, as I found your character to be as I read your letter.

I would not ask about other man in the conversation. It might give her the wrong idea. I would however stick to the topic of eachother, and see where it goes. By this I mean maybe you can start to tell her about personal things..not too private tho. Good things you can remeber as a child, with family, things you enjoyed ect. That will bring her close to you and aslo she might share with you. This would also be the time to find out what you both have in common..music, movies, pets, even tell her a joke..lol A sense of humor is very important. In the mids of things she will also see your serious side, thoughtfulness, at the idea of doing/sharing all this with her.

When you like someone it is not only in the now. When you share she will also find as she learns about you, what you were like. You already seem like a very likeable man. She might fancy some things in your past that might intrigue her. Arouse her curiosity in you, and it will also allow her to want to know more.

My opinion about taking a *respite* from her is not a good idea. This might give her reason miss you, and I'm sure she will. Also remember that there is another man, who you have been honest enough to say that his only fault is minimized to smoking, of which she might not like at all, but on the the other hand she may not care. Also for your sake I would not tell her, or say anything diverse regarding this other man. I would not even speak of him, for the sake of her thinking the wrong thing about you, such as putting him down. I don't believe he is a threat to you at this time. Don't give her a change to think that you are not interested in her by putting distance between the both of you. It might very well make her think you have lost interest in her.

I would not tell her about your feelings for her at this time. I might over whem her. If you think about what I said she will learn of your feelings for her. When you have spent some quality time with her, and you feel she is closer to you than now, then I believe you should. You sound like a very intelligent man and you will know when the time is right. You write VERY well, as time goes on maybe you can write her a letter to let her know also how you feel. You have a very good way of expressing yourself and I'm sure that you will touch her very deeply with a letter and give her something to reflect on also.

Flirting...it is a good way to break the ice. Flirting is really nothing more than teasing. If done in a good way *clean* I think there is nothing wrong with it. Flirting can be anything from teasing her about her quirks, to sexual. Though I would keep the sexual flirts out for now. It might be you like the way she laughs, smiles, talks ect. You can always find a nice way to flirt about things such as this.

Don't feel like it is a contest between you and this other person, try not to read too much into it. The chemistry you feel you saw between them might be she was being polite, or just being friendly in a real way. Try not to let it bring you down. Like I said in the beginning you sound like a very honest, good, caring, and intelligent man, keep this in mind, and own it. It will do no good for become negitive, and it might very well keep you from being yourself, or thinking possitive about yourself.

I found your letter to be very touching, real, honest, and caring..that is you. I do hope you will contect with this woman because I could tell how you feel for her. She is a very lucky woman I might add.

I don't know if this letter has helped you, but I do hope it will give you some encouragement, hope, and give you a sense of the person I believe you are from reading you.

Take care and I wish you the VERY BEST of luck...with the deepest respect....*s*

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