Past Rejections Causing Problems

LegacyUser

So a bit of background. I'm a guy in my late 20s. In my early 20s, I've had rejections from every women I asked out (about 8 through the years). It pretty much caused me to loose confidence and retreat into my shell for most of my 20s and I've been single my whole life. Most of the time, I can deal with it in the sense that normality for me is life tainted by loneliness. Sometimes the loneliness bubbles to the top and then simmers back down again.

Now, I fully realise that a women isn't just magically going to knock on my door one day and I need to get out there and meet people. In every other aspect of my life (work, etc..) I'm a fairly confident guy but all the rejections in the past have seriously affected my ability to even attempt a situation where I might meet someone I like. I know some guys have a problem with talking to women, and I actually don't. I find it very easy to talk to women (actually easier than talking to men) but there is something about asking them on a date (even an informal drink) that brings back all the memories of past rejections and creates this horrible psychological barrier.

If I'm being honest with myself, I've always assumed by height had a big part to play in the past rejections - I'm very short for a guy. Looking at myself objectively, I'm pretty sure I have a great personality and I think my sense of humour is my best quality. On a day to day basis, I really don't care about my height, but once it comes to asking out a girl, I feel like it is big flashing neon sign about me. I feel really powerless and frustrated. If I was overweight, at least I can loose it, but there is nothing I can do about my height.

Sorry, that was a bit long for "background". So for the last 5 or so years, I've been able to live with being single and lonely and not forming relationships. About 4 months ago, I bumped into a colleague in the canteen. She works on a different floor and we rarely spoke before. Anyway, we started chatting and continued our chats over email. The chats got more and more informal and we now have great banter back and forth and she thinks I'm very funny. We share similar interests and I'm liking her the more I learn about her. I bought her a Christmas present which was very specific to her passion in life and she really appreciated it.

I'm sure my problem is obvious - I want to ask her out for a drink, but my confidence problem around this scenario is crippling me. In a way, I wish this whole thing would just go away. I didn't actively set out to flirt with this person, it just sort of naturally evolved but now I really like her.

Logically, I know that the worst that can happen is she will say no. It would be the first girl I'd have asked out in about 5 years and if she rejects me, especially after our good chemistry, it would just make my anxiety about my appearance even worse.

But I feel I've reached a stage where I have to ask her out because otherwise I will always think of it as a missed opportunity. Obviously, asking her out via email will be a little easier and it'll actually seem quite informal - just a way to see her outside of work. But I feel like I'm purposely going down a path of embarrassment, like intentionally stepping on a banana peel. It feels so obvious to me that it is not going to work out, yet I can't stop myself from asking her out despite my 99.9% certainly that it won't end well. It is a strange feeling.

Sorry for the long post, I was basically just typing my rambling thoughts. I'm not even sure what I'm asking here, just a way to unload, I suppose.

ShortyGotLow

I would remove the negativity from your mind before even thinking about asking her out, as women have ways of picking up on that even if it's not obvious to you. Get yourself into a positive state of mind first, and then maybe you could ask her out without actually asking her out. Like meeting for a cup of coffee, not technically a date but getting a better idea of the situation.

As for height, I have 2 male friends who are short (5'5" - 5'6") and they are both going out (1 married) to absolutely stunning, jaw-droppingly beautiful women. Why? They never let their height become an issue, they didn't even acknowledge to themselves that they were below average height. Most women these days are not that shallow and can look past something so trivial, imo - especially if you have an air of confidence that shows you are comfortable with who you are.

Best of luck!

RZoran

I would probably make sure you are not misinterpretating signals and that she really is also interested in you before making a move. No offence intended, and I have made the same mistake, but these things are normally blatantly clear for the most part. Especially if you have been talking for a while and feel like you got a good feel on the situation. The extended talking bit does sort of scream more of friendshippy type scenario to me and if mostly emails/texts then it becomes even harder unless the person really writes it out because electronic interpretation is never a good idea. Basically for no other reason than you work in the same location, and you already have problems with confidence, I would probably advise against it unless I was pretty sure the feelings were mutual. I would suggest getting used to asking for contact details or going for coffee etc. with people you won't necessarily ever see again if rejected or don't have anything/much invested in. Rejection is a part of dating so it would be good to get that monkey off your back and help build even a facade of confidence when it comes to this. As for height, I am tall and often thought I would like a bigger body type. Not exactly uncommon to have problems with ones self-image but just like there is girls that only like tall guys, there are plenty more that could either careless or actually have a preference for shorter.

LegacyUser

Thanks for your reply.

I know what you are saying but I really feel I have past a point of no return in regards to how I feel about this person. Asking her out is a big risk but don't I can move on without asking her out. If she says yes, great. If she says, at least I have tried and I can move on. I think at the moment, the uncertainty is the worst. I can't move on knowing there is a possibility there.

All I'm planning on doing is asking her to go for a drink after work as it would be great to talk face to face. If she says no outright, that is a pretty clear sign. If not, at least I will be face to face to I can better read the situation.

Obviously things would be easier if I didn't work with her, and I'm not going to lie, a rejection will hurt but I know I will get over it with time.

I know it sounds like I have already made up my mind, but I'm wondering if I am missing something obvious.

milli milli

OP I think you have your mind made up and I think you should go for it.
She could say yes or no, that's all. They're won't be earthquakes or referendums or anything dramatic like that! She'll just either say yes or no.

I really hope things turn out well for you. You sound like a nice guy and you deserve happiness with someone.
But try not to take it too personally if she says no.
I've turned down guys in the past - there was nothing wrong with them, they just weren't the right match for me.
Although please if she says no, take it graciously and don't go saying you weren't asking her out on a date. This happened to me recently with a friend and it was so awkward. I didn't want to stay friends with him after that.

LegacyUser

It sounds like you're going to ask her out either way. I'm not sure why though when you're 99% sure she will say no? Do you know is she single? About the height thing, all women are different, some it really matters to, some not so much. It's not about women being shallow, it's more you have to be with someone you're attracted to physically in one way or another. Is this girl taller than you? Most women will go for a man at least their own height. Not many will go for a guy who's shorter than them, but again it's down to their individual preference. If you really do like her then you're going to have to let her know you like her, if she's not already suspected it, and see if she reciprocates, maybe try and suss that out before asking her out because if she says no it will be awkward etc as you work at the same place.

LegacyUser

Again thanks for the replies.

She is the same height.

It is strange...I'm always switching between two perspectives. The logical side thinks I might have a chance. I mean I'll only be asking her to drinks one evening not marriage. It is mostly for her to get to know the non-email me and vice versa.

The other side thinks about how I've never been successful asking a girl out and it is difficult to shake that. My 99% certainty that she'll say no is not based on any real thing just my horrible anxiety about asking out a girl for the first time in years. As I said it isn't logical but that doesn't make it any less real.