Older woman - do I ask her out or not?

Discussion in 'Does She Like Me?' started by cosmogramma, Sep 5, 2016.

  1. cosmogramma

    cosmogramma Member

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    I'm a long term follower of these boards but a first time poster, and I would massively appreciate any advice.
    Apologies for how long and painstakingly detailed this is going to be - I want to give a clear picture.

    I'm temporarily working in a shop between postgraduate degrees, and a few weeks ago a woman many years my senior came in and we got talking and immediately seemed to hit it off, talking openly like we had known each other forever. It turned out that she's the managing director of a company vaguely related to what I want to do, and that she had a friend who runs a company in exactly what I want to do. She offered to meet for coffee so that she could introduce us to one another with the possibility of me working for him. I texted her and she sent a friendly text back letting me know that she'd get back in touch about meeting up with her and this guy she was telling me about. The next day, she came into my work with her mum, saying to her mum "this is .... who I was telling you about", also acting nervous and telling me that "I'm surprised that you remember me". Prior to this I hadn't thought of her in a romantic sense, but I got the impression that she was attracted to me from this. The first time I had met her she also commented that my eyes were "lovely" and looked at me wistfully. I'm 99% she's gay from a whole host of factors about her demeanour and appearance.

    Anyway, after this I didn't hear from her for a while, so sent her a text about the meeting, which she didn't respond to. Eventually I emailed (she jotted down her work email address as well as her mobile number), and received a somewhat cold, concise professional email which she forwarded to her secretary asking her to try and arrange a time that would be convenient for her and the guy she wanted to introduce me to. I understand and appreciate that she is very busy and important, having an organisation to run, but it was a striking contrast from the warmth and openness that she exuded with me in person.

    Fast forward a couple of weeks and she eventually calls me to say she's sorted out a meeting between us and the guy. I immediately notice how awkward and shy and flustered we are with each other. After introducing us both and chatting for a while, she asks if we would like her to leave so that the guy and I can chat about me potentially working for him. I tell her that I'd like her to stay, that it's nice to see her, and lament the fact that she hasn't been into a shop for a while when I've been there. She shyly replies how good it is to see me too, and that she had been in the shop but that I wasn't there at the time. I notice her taking glances at me. She also told the guy "I met ... and was just incredibly impressed by her, and I walked out thinking that an encounter like that doesn't happen everyday". She also joked to him when I was talking that she "wanted to take me home". She kissed me on the cheek when I left and when I arrive, but I understand that this is just a friendly way of greeting somebody you're friendly with so shouldn't read too much into it. It was just how awkward/nervous she seemed around me, and I picked up sexual tension vibes between us. I texted her that evening thanking her for arranging the meeting, and telling her which days I would be in the shop later that week, that she should drop in and say hello if she got the chance. She didn't reply so I just thought I would leave it from then on.

    Anyway, a couple of days later she did drop into my work specifically to see me (she didn't buy anything). She called my name from the other side of the shop and gave me a big hug and kiss on the cheek when she saw me, and seemed genuinely thrilled to see me. We chatted for a few minutes before she said she'd better go because my boss was glaring at her for chatting too me for too long, and she was off to ride motorbikes with her friends (gay much - haha). So she left and I told her to text me. Now it is the evening after this encounter, and I want to text her to ask if she would like to go for a drink or a coffee with me sometime, without the guy. I really feel something between us and would like to get to know her better. The thing is, I feel that I'm getting mixed signals because she seems to either not reply to texts or reply in a purely professional manner, yet is very open and flirty and attentive with me in person. But I feel that there is a chance of something happening if we meet on our own.
    I know that she has an incredibly high pressured job which she lives and breathes, and so I don't want to pester her (and I'm also scared of her ignoring me and perceiving me as some annoying kid) but at the same time I really like her and get the strong impression that it's reciprocated. So do I ask her out or not?
    Sorry for the essay - thanks for sticking with me for this long if you read all of that!
     
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    Last edited: Sep 5, 2016
  2. Bluenote

    Bluenote Well-Known Member

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    When people give you a split impression like that, there is something - usually something not good - going on behind it.

    She is a take the initiative kind of woman, but she is intentionally keeping barriers between the two of you. There likely is some reason for it. No idea what the reason is - if she is kind of seeing someone, if she is not ready for anything serious, if she has reservations about your age. It could be lots of things. But clearly, she is keeping you at a bit of distance.

    It is one thing to meet someone and have an instant attraction. It is another thing for that attraction to be enough to carry a relationship - casual or serious. And it is yet another for the attraction to get people over social barriers, expectations and stigma about things like dating someone much younger, having a casual thing, etc...

    My guess is that she wants to go there, but is too disciplined to actual go there. Hence the blowing you off in text.

    I say be thankful for the career connection, but don't try to instigate anything romantic / sexual with her. If she wants that, she is the type who will initiate it.
     
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  3. cosmogramma

    cosmogramma Member

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    Thank you so much for your thoughtful advice. I agree with you that she seems to be purposefully holding back from me and I'm not too sure why. I can completely understand why she might find the age difference to be an issue.

    I sort of get the impression that she is somebody who thrives in a professional sense but perhaps at the expense of her personal life. Without wanting to sound big headed at all, I am generally considered conventionally attractive, and she seems fairly shy, so maybe she just thinks that I wouldn't be interested in her in a romantic sense. I also think that because she's older, maybe she doesn't feel comfortable approaching me romantically because she doesn't want to come across as a predator or whatever. But maybe this is just wishful thinking and I should leave it be. I just think it's a shame to waste such a strong connection without seeing what could happen.
     
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  4. Bluenote

    Bluenote Well-Known Member

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    Well, you have given her clear signals that you are 'open to more.' You have initiated texting, returned her hugs, been happy to see her. I think that takes away any 'well, maybe she isn't sure how to read me' argument.

    What is the age difference between you two?
     
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  5. cosmogramma

    cosmogramma Member

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    True. I'm in my mid-twenties and she's forty-ish. I've been in a relationship with a similar age gap and it wasn't an issue. But it might be an issue for her I suppose.
     
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  6. cosmogramma

    cosmogramma Member

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    It would be really good to hear other people's perspectives on this.
     
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  7. Spygirl

    Spygirl Well-Known Member

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    Being a 40-ish woman, I think my interest in someone who's in her mid-twenties would be based on the physical -- but I would quickly rule out any kind of relationship. We're just at two different stages of life....I'm past the bar hopping, settled financially, have my career in order. Very few people in their mid-twenties have their shit together, so-to-speak. And I don't mean this to sound like an insult to you at all....but the idea of visiting someone who might have a roommate or isn't settled in a career or financially is a bit off-putting.

    So...perhaps she does find you attractive.....but perhaps she recognizes the inherent difficulties a relationship with someone of your age would bring. And, there are exceptions to every rule..maybe you are, but the only way for her to know that would be to get to know you better.
     
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  8. Emm

    Emm Well-Known Member

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    I'm going against the grain here but...
    Throw caution to the wind, ask her out for coffee or something.
    You seem pretty level headed, you take your career progression seriously, you're between post grads, you've dated a similar age gap before so I'm guessing you have the maturity to make something work.

    Chance encounters that are meaningful to both parties aren't all that common, seize the momentum and see where it goes
     
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  9. cosmogramma

    cosmogramma Member

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    We're going out for a drink later on in the week, so I'll see how it goes. Hopefully I can get a better idea of whether she's interested or not.
     
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  10. BeckyFair

    BeckyFair New Member

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    Firstly good luck and hope when you meet for drinks, it all goes well!

    If I were you, when you meet up I would be very open and show a real interest in what she does outside of work.

    She has already spoken about an interest in motorcycles so why not start with that? If she's still not opening up at all then I think it might be time to let it go.

    I agree with other comments, it may well be that she was, and perhaps is still, attracted to you, but you are at very different stages of life. She may have simply made her mind up that because of that, a relationship just isn't something that she wants to pursue. You tried anyway at that stage, and you deserve for your attention to be focused on someone who truly appreciates it.
     
    #10
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  11. Eloise

    Eloise Well-Known Member

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    Just got here. How did things go when you met for a drink? I tend to think there's something there. Would be nice to know if anything becomes of this.
     
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