How to/should I approach her,

[Bart83]

Not even sure asking this on here is a good idea, because I'm in my thirties and it feels a bit like mushy school-yard stuff.

I've been single for ages, partly because I am a fish out of water around women, and partly because I just haven't been that bothered about trying to find someone. I'm not the best looking guy in the world -- I don't think anyway -- cripplingly shy, a bit moody and over the last few years I have kind of stoppoed looking after myself. Put on weight, not really put much effort into how I look, etc...because I've not been that interested in meeting anyone. No one that I've met that I've been interested enough in to make the effort anyway, and being consistently rejected isn't worth the hassle anymore. Too upsetting. I'm not very confident and have very low self-esteem.

However, there's a woman who is a friend of some other friends whom I often see in the local village that I have become really interested in. I've never really spoken to her, except on the odd occasion when I have been invited by our mutual friends to sit at their table in the local bar. I get the impression she is single, but I'm not sure. There's just something about her that I really like -- she's extremely pretty, but also very quiet and kind of looks a bit moody and miserable all the time, but I really like that! Still waters run deep, as they say, and I'd love to know what goes on behind her gorgeous eyes. I just don't know how to even go up to her and approach her. I doubt she'd give me a second glance, and even if she did I think she might be bordering on being a bit too young (I'm 33 and I think she's 25/26). I'm also worried about embarrassing myself in front of our mutual friends, because it would be the talk of the village within a day. Not really said anything to them for the same reason. When I see her, it is usually in the bar at the weekend, and she is usually with her friends.

Not really sure what to do. I go out at the weekend and keep hoping to see her, think about her quite a bit etc...Thought about sending her anonymous flowers, but that might a) creep her out b) cause trouble for her if she's not single and c) would not really get me anywhere because she'd not know they were from me. On the other hand it might really make her day, even if it doesn't break the ice with her.

If I thought there was even a chance she wouldn't slap me down straight away I'd maybe just go for it, but I get rejected 99% of the time I've approached women in the past, hence why I've kind of given up on finding love. To be honest, I don't really like feeling like it anymore, because it's wishing for something that I just know will never happen, and it's not worth the dissapointment. Dunno what to do 🙁

[pcmaster]

I think you should just be ready to make a fool of yourself and go for it. Its a tricky situation but even if you fail then dont stop and come back better next time.
Flowers are good if you give them directly. Anonymous flowers are pointless.

I would say something unussual but it could help you learn from ussual guys mistakes. If you create a fake dating site account with a pretty female pic then you would get hundrets of messages from guys and you will see that most are ither too needy or too serious at the begining or too simple - Like saying Hi, or Hey and some random smiley. That kind of messages dont ussualy get responded.
But we are talking about real life. if you go on to her and talk with her like you really dont need anything from her then you could have a chance.
Like you could go to her and say like - I see you here often, would you like to communicate? or I see you hang here a lot, you must have like coffee they giving here. - You see something unneedy and simple. Also you should find out if you are person who looks better with smilling or without. If smile dont make you look prettier then dont smile.
Besides that also work on your style and looks.
Its hard for you to approach this girl because you like her, you think about her and you had negative experiences in the past so you might not want to ruin this one. But in order to become good with this girl you have to become good with girls in general. If you fail with 99% of girls then what is the chances you will be lucky with this one.
If you have like spare 4k then I suggest a boot camp for picking up girls. Good ones in UK are Sasha daygame and Kesia Noble bootcamps. You can look up these guys on youtube and see what they are all about. Basically just search Sasha daygame pickup or infield and then see how he talks with girls and how much information he extracts in short period of time. The goal is to get phone number or something that will help you get in touch with her later.
I want to help you so stick around and let me know how things going, I have much more advice and resources available.

P.S. You wont do everything right. Just start, make mistakes and learn from them.

[breathe123]

33 & 25 is a right age range, not too young for you. Ask common friends if she is single first before making any move. Do you feel is is a " the one " type for you? If so & she is single give it a good try & ask her out for dinner or coffee or even a movie.

No, don't send anything anon, that is creepy. Be upfront, people respect that.

[TheEvilJester]

Believe me.... I SO understand how you feel. I mean, cripes, your post basically could have come from me, that's how much you sound like me. For me, this has been a life-long struggle. Sometimes it feels hopeless to ever find love. The thing is... if you give up, then it IS over. It is worth it to keep trying. I would not wish my dark fate on anybody. If love is something you want, then do not give up on trying to find it. Honestly, sometimes asking women out IS 99% rejection. It's unfortunate, but true. Often times if you ask 10 girls out, you'll be luck if even one says yes. ....Or sometimes you will be lucky and won't even get to 10 because one will say yes before you do.

I think pc's suggestion is pretty good. If you feel like you aren't good at asking women out, maybe try a "boot camp" or class sort of thing to learn how to be better at it. Honestly, though, the bottom line is it just takes being more comfortable in your skin. Don't approach a gal like she is THE ONE. She could be, but you don't know that. Approach a girl as though you like her and want to ask her out (or else why would you bother) but that it wouldn't bother you one bit if she said no.

Believe me, nobody likes rejection. But, if you don't try out of fear of rejection, then you will just always psyche yourself out. And, believe me, I know all of this is so much easier said than done, but it really is true. You CAN do it. Believing in yourself is the first step. Then, you also need to realize that... as much as you feel you would be lucky if any particular girl said yes to you..... she really should feel just as lucky to get a chance to be with you. Any gal would be lucky to have a good guy like you, and any gal that can't see that or even give you a chance didn't deserve you anyway.

I am NOT suggestion you become a cocky jerk. I'm not suggesting you act like you are God's gift to women and they should be falling all over you. I'm just suggesting you realize that you are awesome. As the saying goes, don't put these women on a pedestal. They are just human beings as well.

Good luck to you. Sincerely. From somebody who has suffered from the same troubles in life, I sincerely wish you the best in finding your way to happiness.

[pcmaster]

Honestly like month ago I was at the point if I would have recieved one more rejection my dick would fall off. but I got lucky and got a chance with amazing girl that changed my life to a more positive note. So again, AGAIN(so many times it happened before) I realized that its not worth giving up that theres always a chances, always some amazing girls are out there for me to meet. And there are for you too guys. Just live like you can meet them, dont let yourself go, take care of your soul and body cause you will want that edge, that something that will help you get those amazing girls once you will encounter them and it will be all about who you are and how you lived till the moment till you met that girl.

[Bart83]

Thanks for the replies. I'm pleased I asked for advice before I did the flowers thing, because the consensus of opinion seems to be that it would have been a bad idea.

I'm not going to say she is the one, but there is something about her I find really intriguing and enchanting.

I can think of one of our mutual friends whom I'd feel comfortable asking if she's single. I don't know this friend very well, but I don't think she'd be judgemental or indiscreet if I casually asked after few beers. I could then dismiss my casual enquiry as me being drunk.

I wish I could believe that stuff about someone should feel lucky to be with me, or that I'm awesome, EvilJester; I just have no evidence to justify feeling that way.

[TheEvilJester]

Oh, believe me, I know that from a LIFETIME of experience. So, trust me, I know that is so much easier said than done. You'll get there, though. I think that is even more important than finding love... is finding love for yourself. I took me a LONG time. Honestly, basically until just recently. It's still a daily struggle and always will be, but I got there, and it was worth it. I'd still love to believe that fate will some day prove me wrong and I'll find that special someone.... but these days I am learning to be happy just with me. ...And you know what? IF some day I'm actually proven wrong and I DO find that special somebody.... It will be even THAT much better because I no longer NEED them.... but I still want them.

I may know exactly how you feel.... I may believe there is no hope for me, no chance to ever have a love life again..... but that doesn't mean I will give up. That doesn't mean I will stop being open to the possibility. And that doesn't mean I won't try if the opportunity actually does arise. I think it is so much more important to get there. Be happy with YOU.... but open to finding somebody. Believe me, I know that isn't easy, but it is worth it if you can get there.