Horrible at reading women/dating etc, and want to try and ask this woman out, advice?

Ok so some background on me - 24, never had a girlfriend and never gone past a second date. I've asked a girl out once before - about a year and a half ago - and it still bothers me but its gotten better. Very low self esteem and confidence as well even though I'm happy with my appearance and happy with my personality when the social anxiety doesn't get in the way.

So there's this girl at work; I don't talk to her much because she is usually out doing field research. We are both pretty shy, but I'm even more shy (I have social anxiety disorder) - she's usually the one to start any conversations, say hi, that kind of stuff. I've tossed around the idea of asking her out for something for the past month or so now, and today its just driven me crazy all day - it was all I could think about. I guess that's because today she was at work for longer than usual and I had a chance to talk to her a bit more. She came up to the front desk to talk since we hadn't spoken in a few weeks and that was really my chance and I blew it. every time we talk I ask her what her plans are for the weekend she always tells me nothing really. So I've had my chances but I always bail and f*** things up...

My gut is telling me she is probably somewhat interested - but for whatever reason I just can't do it. there's always people around, its never just me and her. I'm not sure if she has a boyfriend as I Haven't spoken to her nearly enough - she hasn't gone home once this summer so I'm kind of thinking maybe she doesn't?. I'm absolutely terrified of asking a woman out who already has a boyfriend - its a huge fear of mine. Our last day at the job is Thursday but I'm away until Wednesday so I pretty much have 2 days (assuming I even see her). She also is going back home about 3 hours away so now I'm thinking what exactly is the point now? What am I trying to accomplish with all this?I don't know what do do at all, don't know how to ask, when, to do what - I don't really have a clue what I'm doing; I'm just worried that by next Friday I will have f***ed up yet another opportunity


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Most Helpful Guy

  • What is the point now? To establish a connection, maybe? To have shown your true feelings so she doesn't think it was just nothing, and you really did like her?

    And you have already said what you want to accomplish here, you wanted help with your A.D., and, more closely, you wanted to ask her out and show her you liked her. I can sympathize with your shyness, but you need find courage, to give yourself courage. Don't build on thoughts of fear of NOT doing it, build on thoughts of success and fulfillment of DOing it. It may be scary, hell, it can be worse than anything, but sometimes we need to risk that much for the reward it brings. We take that chance, knowing we may fall, but we remember the prize, and it give us courage, the courage to move, to take that leap into the social darkness, to ask and see, despite the fear.

    A wise person once said "Courage is not the absence of fear, but action in spite of it". So it's okay to be afraid, but courage to win though it.

    And I will now go through the obligatory "What's the worst that could happen" not knowing what things are truly like from your point of view.

    She says no. For whatever reason, that's not entirely important. But you know what's worse? Everyone will know. Everyone will know that you asked her out, and she turned you down.

    Or, wait... maybe it'll just be you and her. And she doesn't sound like a mean b*tch, (neither do you, btw)so maybe you won't be a laughingstock. Maybe, it'll just suck. And yeah it sucks, but you know what? She is not the only female you are ever going to be attracted to. But if you ask, no matter what she says, I think that's a victory, and huge victory. It mean's you're taking control of what you want to happen in your life. Even if she says no, sorry... you still made that step, and then it'll be all the easier to make that step with the girl who WILL say yes. Because trust me, there will be a woman, I don't know when, but there will be; Who will love you more deeply than you can conceive of right now.

    So have courage, in the face of your inner fear. If she's shy, she'll likely have noticed that you're shy too, so I'd bet she could sympathize with your predicament. You see her, you can say hey, if there's something to talk about, talk then ask, if not, just ask. Straight out. It's not a shameful thing to ask. Far from it. Everyone knows what it's like to ask someone out (well, most... you know what I mean), so it's not some freaky thing that only you do. Be straight, be cordial, and just ask "Hey, could we like... meet before you go?" or something like that. You just ask for what you would like to happen.

    Courage brother, and inner strength. The fear may be great, but it comes from within you, so with you must have courage to match it. Find that courage.

    And then make sweet remixes about it.

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    • Thank you for your response - courage is so hard for me to find because once I'm in the situation, my head just shuts down - the person will be talking to me and nothing will register. I always think about what I need to say not to screw things up, I always think about things I cannot control, my heart races and I almost lose my voice, further lowering my confidence. I know I need to do something to calm myself down and almost get myself excited instead of panic

What Girls Said 2

  • Aww, you poor thing! I find it terribly adorable how shy you are, and I'm sure the girl you like does too. Well, my advice is to just stop worrying about being rejected, her having a boyfriend, or any other doubts you might have and just ask. I know it seems like a huge task and there are many factors to consider, but once you've overcome the initial fear of asking her out - you're halfway there. What's the worst that she could say, really? Just find a time where you're both not too busy and look into her eyes, and gently say, "Since work's almost over, I was wondering if you would like to go out sometime. I'd like to get to know you better.." Then smile and await her reply. If she says no or has a boyfriend, then don't act scorned - just accept it and move on. You might want to get her number as well, if you already haven't so that you guys can keep in touch. :3 Hope this helps.

    @overthetop67: Oh, and I really liked your answer. This should help him a lot.

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    • Thanks for your kind words - I try and tell myself exactly this as much as I can but its like I don't trust myself. Maybe its because I felt the same way I do now with the last girl I asked out and was turned down

  • Just ask her out.

    You probably should get some help with that social anxiety.

    I'm also not sure why you knowing you have social anxiety don't try to work on it by asking out girls

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    • Ive gone through counselling, and I've been on antidepressants/anxiety meds for 3 years now. Counselling didn't help me, and I struggle sending emails to people, let alone asking them out on dates - if it was that easy for me to just go out and try I would have done that many many years ago.

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    • The thing is I know I'm not ready for a relationship, and believe me I feel like crap because I tell myself I'm going to burden them by asking them out - that goes through my head all the time and is partially why my confidence is so low. I guess I want to do this for personal development more than anything, but really I don't know.There's nothing else I can think of that can fix my anxiety issues

    • Try going for casual dates/hookups before going into anything serious.

What Guys Said 3

  • Work relationships are very delicate and explosive, this isn't a good idea for anyone, but especially someone who is shy and not very experienced. Especially if you're 'terrified' about it.

    How is it yu don't know if she has a boyfriend? Don't people at work know if she does or not?

    And there's nothing wrong with directly asking her that if you need to. Go ahead and ask her anything that will make you less terrified.

    But regardless of those questions, I'd advise you to try someone less problematic As you say, she'll also be far away soon..

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    • You're absolutely right about work relationships - however in this instance we are both temporary employees, probably not going to work there again. She does a lot of field work with a couple other people (whom I also don't talk to and have since left) and is rarely in the office - there's no one in the office that knows much about her. As I read through these answers, I'm starting to think that maybe I want to do this so badly for my own personal development since I've failed far too often already..

    • I'd still advise you to try someone without all these built-in obstacles!

  • me and you both pal, I'm almost 24 and still in the same boat because of Asperger Syndrome, I hate how people say that is not an excuse, that it is a problem you can overcome, you can't change genetics you know

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  • I can relate to you like you have no idea. All I can tell you is to work on you, work out hard, work on your hobbies, get out as much as you can with friends or whoever. Social anxiety will go away as your self esteem goes up.

    About the girl...ask her if she is seeing anyone...carefully look at her response...if she says she isn't seeing anyone and smiles at your or acts positively to you asking her that...then, imo, you have the green light to ask her out. When you ask her anything like that do it casually, don't make a big deal out of it- because it isnt.

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    • Asking a girl straight up if she's seeing anyone - for me - is more terrifying than actually asking her out. Its almost as if by doing that I'm prolonging the stress longer than it needs to be.

    • When I use to feel like that I just didn't bother trying to date...I just worked on myself until I felt a lot more comfortable with who I am...working through internal conflicts until largely resolving them and being at peace to some degree...only after doing lots of that did I feel confident enough to talk to girls with more ease. gl

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