A
male
age
41-50,
*owerslam
writes:My friend's sister turned me down for a date after initially accepting a few days earlier. Anyway since then we've been out a lot in the same social circle and she's been sending some strong signals.She's kissed me on several occasions but always when drunk and at the end of the night. The other day she told me that she had hinted at her brother that she might like to date me and that he went crazy saying no way.Kind of insulting seeing as i'm a good friend of his.I got the feeling that she wants me to ask her out again.My question is should i ask after being rejected once seeing as it would probably make things awkward if she wasnt into it and also she is a little afraid of her brothers opinion. What to do?
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female
reader, Dorothy Dix  +, writes (2 December 2010):
Hi. I still think that you should try and get to talk alone to her on Saturday night at her brother's function. It probably shouldn't be too difficult to organise that, throughout the night.
In the end, the real decision to go out with you, should be made only by her - not her brother. Surely she knows her own mind enough and her gut instincts at 28, to know when she sees a decent young man and to be able to identify a man who would mistreat her.
Just by the way a man speaks to her - with respect, and to be genuinely interested in her and her life. Even when talking to a complete stranger, she could tell if he was a decent type or not.
It would seem that because she already knows you pretty well, that she should be a good judge of your character by now.
Anyway, just enjoy Saturday night, and be friendly and keep it light with her, and see how it goes.
Don't apply any pressure for her to go out with you, just stay friendly but nothing more.
A
male
reader, powerslam +, writes (2 December 2010):
powerslam is verified as being by the original poster of the questionThanks Dorothy for your advice. Very wise and helpful. I do think its unusual that a grown woman needs approval from her brother. The thing is i'm 30. he is 22. she is 28. I've been good friends with her brother since we starting working together 18 months ago. Me and him drink together every weekend and he always asks me for advice. He's critical of everything his 2 sisters do all the time. I think he's protective because of bad relationships they've had in the past. He's always negative about their intentions when they talk to others (outside of me and before i developed this crush).The thing is i know they both are afraid of his lectures. I had to hide the fact that one sister fell recently while out drinking because he'd assume she was very drunk when in fact she just slipped. To be honest i don't want to give up on something that may be there but i'm old enough to know that quitting is better then wasting your time on something that will never happen. The thing is for once i am totally confused about which route to take.Once again thanks for your advice, it was very insightful
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A
female
reader, Dorothy Dix +, writes (1 December 2010):
Hi. I think that she probably does have genuine plans to see her friends on Thursday nights, just like she said.
If she was making it up, she would have first hesitated (like she was thinking of what to say), then maybe said something like - "Ah, um, ..... no, I can't because I'm going out with my friends, which I always do on Thursday nights to catch up".
In any case, when a person is lying, there is usually some hesitation and calculated thinking - it always seems pretty clear. If she didn't hesitate and just came right out and said it right upfront, then you can be almost certain that she was telling the truth. That's a positive thing.
As you are seeing her on Saturday night for her brother's function, just let things ride and relax till then.
Once Saturday night arrives and you are there at the function, just be friendly and keep it light and just gauge how you think the night is going (how she is acting towards you), then and only then if it feels right to you, well then somehow ask her - when there's no-one else nearby to hear you - if you could talk. However, only do this if it does feel right and she seems to be sending you friendly signals.
Because whenever she sees you on a night out with all your friends, you said that she comes up to you at the end of the night and kisses you. Of course, that probably isn't the only time she comes up to you, surely. She must talk to you from time to time as well throughout the night.
The main thing is, she obviously likes you a lot as well, so it's not one-sided. The only thing standing in the way right now, is her brother's apparent non-approval.
Have you spoken to her brother about asking her out yet? You do need to do that, just to find out what his objections are. It will at least clarify things for you.
If you can speak to him before the function on Saturday night, all the better. You need to reassure him how you do feel about his sister, and that you don't want to hurt her or mistreat her. You could even mention the types of places you'd like to take her - such as the movies, a nice restaurant, a picnic, see a show etc.
I just thought of something that's important. Perhaps his sister has been in those relationships called - Friends With Benefits (FWB), where the guy only calls when he wants sex from the girl, but never bothers to take her out to nice places and spend money on her. In these hookups, a hookup is all it is. It's simply a case of the guy taking the girl for granted, just as long as she keeps on saying "yes" to him.
This is a common occurrence in today's society. If this has happened to her in the past, she's probably been upset by it, because she has wanted more than that and then she's been hurt by it. So maybe her brother is thinking about that. He's hoping that you aren't the type to treat a girl like that. Some men are, though.
If you can convince him that you will treat her well and with respect - and be genuine - then you might get his approval.
You haven't said her age, but how old is she? Is he the big brother?
It's unusual that a grown woman should need her brother's approval to date someone. Do you think that?
Is there more to this than you've said already?
Let me know, so I can help you more.
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A
female
reader, Dorothy Dix +, writes (1 December 2010):
Hi. I think that she probably does have genuine plans to see her friends on Thursday nights, just like she said.
If she was making it up, she would have first hesitated (like she was thinking of what to say), then maybe said something like - "Ah, um, ..... no, I can't because I'm going out with my friends, which I always do on Thursday nights to catch up".
In any case, when a person is lying, there is usually some hesitation and calculated thinking - it always seems pretty clear. If she didn't hesitate and just came right out and said it right upfront, then you can be almost certain that she was telling the truth. That's a positive thing.
As you are seeing her on Saturday night for her brother's function, just let things ride and relax till then.
Once Saturday night arrives and you are there at the function, just be friendly and keep it light and just gauge how you think the night is going (how she is acting towards you), then and only then if it feels right to you, well then somehow ask her - when there's no-one else nearby to hear you - if you could talk. However, only do this if it does feel right and she seems to be sending you friendly signals.
Because whenever she sees you on a night out with all your friends, you said that she comes up to you at the end of the night and kisses you. Of course, that probably isn't the only time she comes up to you, surely. She must talk to you from time to time as well throughout the night.
The main thing is, she obviously likes you a lot as well, so it's not one-sided. The only thing standing in the way right now, is her brother's apparent non-approval.
Have you spoken to her brother about asking her out yet? You do need to do that, just to find out what his objections are. It will at least clarify things for you.
If you can speak to him before the function on Saturday night, all the better. You need to reassure him how you do feel about his sister, and that you don't want to hurt her or mistreat her. You could even mention the types of places you'd like to take her - such as the movies, a nice restaurant, a picnic, see a show etc.
I just thought of something that's important. Perhaps his sister has been in those relationships called - Friends With Benefits (FWB), where the guy only calls when he wants sex from the girl, but never bothers to take her out to nice places and spend money on her. In these hookups, a hookup is all it is. It's simply a case of the guy taking the girl for granted, just as long as she keeps on saying "yes" to him.
This is a common occurrence in today's society. If this has happened to her in the past, she's probably been upset by it, because she has wanted more than that and then she's been hurt by it. So maybe her brother is thinking about that. He's hoping that you aren't the type to treat a girl like that. Some men are, though.
If you can convince him that you will treat her well and with respect - and be genuine - then you might get his approval.
You haven't said her age, but how old is she? Is he the big brother?
It's unusual that a grown woman should need her brother's approval to date someone. Do you think that?
Is there more to this than you've said already?
Let me know, so I can help you more.
...............................
A
male
reader, powerslam +, writes (1 December 2010):
powerslam is verified as being by the original poster of the questionThanks for both your advice. Anyhow i bit the bullet and rang her. We had a nice chat as we always do and then i asked her if she would like to go out tomorrow night. She declined nicely saying that she always goes to her friends on a Thursday for a catch up but that she would see me Saturday anyway at her brother's gig which is were we generally meet save for last Saturday night when she rang me to see where i was and came to meet me with her friend. I have to say she was a bit drunk but as soon as she came in she was kissing me and feeling me quite a bit.We then met on Sunday for lunch with her sister after she contacted me and went up to a friend of hers' house for a few hours.My question now is, was she politely letting me down or did she genuinely have plans. I.E: Should i clarify where we stand with her on Saturday night or does that just look desparate?
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A
female
reader, Dorothy Dix +, writes (30 November 2010):
Hi there. If she is giving you signals and at the end of the night has often kissed you (when she's had a few drinks), it seems as though she feels at least something for you. It seems obvious.
Because of this, perhaps you could somehow separate her from the group for a few minutes, to talk to her privately and simply ask her. When you're all standing fairly close in your group, you could even whisper quietly to her if you could speak to her alone.
When you do talk, let her know that her brother doesn't seem to approve of you asking her out, and see what she says about that.
If her brother is older than her, she might be influenced by his opinions a bit - out of respect.
Another thing you could do, is speak to her brother and ask him about his objection to your taking his sister out. Then, you hear it directly from him about his concerns.
The short answer to your question is, yes, I think you should ask her out again, but not before you speak to her brother and find out what's going on with him. He must have some reason.
He might just be watching out for her, because he doesn't want to see her get hurt. She's possibly been hurt by men before, this would make her very wary in future.
In any case, just take it slowly, and see how it all pans out over time. Don't pressure her too much to go out with you, just get to know her a bit more, and take an interest in her and her life, and treat her with respect and kindness.
When her and her brother both see that you seem to genuinely care about her, everything will eventually change and it will also flow a lot more smoothly.
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A
reader, anonymous, writes (30 November 2010): did you ever think that maybe the reason she turned you down the first time it was because her brother disapproved
i mean if she is sending strong signals now and was prolly the last time than all of a sudden you hear her brother say noway then it was prolly him the whole time cause i no i would never go out with a guy if my brother dissaproved of him
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