How to transition from chit chat to asking somebody out.

[TheEvilJester]

I recently posted a thread sort of just musing about how I feel like guys all seem to have this innate, natural ability for the "cold approach." To just go up to a complete stranger and ask her out. I felt alone in that I just cannot do that because to me it just feels too unnatural and also kind of "icky," in a way. I was very pleasantly surprised to see that most peeps on this board are apparently not really all that fond of the cold approach either, and for a lot of the same reasons I am not.

To me, it is just so not in my nature to just ask a complete stranger out. I tend to like to know somebody a little before taking that plunge. Frankly, in the past I have been much too shy to take the plunge even then. These days, I am still pretty ridiculously shy... but I feel like I finally CAN force myself to start giving it a shot. I finally realize I'm not going to get over all that if I don't MAKE myself get over it, and I finally feel like I CAN do that......

Problem is, now these days I don't really have any "prospects" so to speak. I sort of hate to word it like that, because it almost sounds like a job search or something. LOL! Suffice it to say, though, I just don't have a lot of opportunity to meet new people, much less women these days. In your younger days, you meet people at school, work, through your friends, etc.

These days, what do I have? At work, I don't really meet many women outside of my own department, and even those I do somehow are already married or at least in a relationship. About the only places I see women these days otherwise are on my train, at the gym, when randomly out and about, etc. None of these are really terribly conducive environments to striking up a conversation with a complete stranger. But, I guess I have no choice. I will have to.

So, long story short (too late, I know) I am starting to think I have to learn to just approach random women and learn to start talking to them. That's daunting enough....

But here's the part that really throws me...

How do you make the transition from chatting to actually asking her out? From what folks said in my previous thread, it sounds like most of you agree with my aversion to just going straight up to a stranger and asking her out. Folks in that thread suggested instead chatting it up first.

So, how exactly do you make the transition? I feel like, me in my infinitely shy ways, I would just be hoping there would be some natural way I could transition, but that would probably never come. It's weird. I don't know why it seems so foreign to me, but I just feel so awkward about the idea of asking a gal out, which is part of how I wind up always psyching myself out.

Anybody have thoughts?

[Wakeup]

Start by participating in things that you are interested in. If you see women there then you have something in common to talk about. That's why I suggested that you join meetmarketadventures.com or meetup.com and pick an adventure that you like to do.

Get a dog... you will have women cold approaching you and your adorable puppy will help along the convo.

[solarion]

A stranger is just a potential friend you haven't gotten to know yet. You start out by just getting comfortable talking to people you've no reason to talk to and you build on it.

Get a dog... you will have women cold approaching you and your adorable puppy will help along the convo.

...or a niece or nephew. A friend's kidlette. Women often fawn over a guy with a youngling in tow and no matriarchal figure in the frame.

[Jffs24]

Got any party friends, you know the types ,they throw a big rager every weekend -- get yourself at one of those, there'll be girls a plenty around and you can chat up many and if you drink take a few for courage and just be friendly, amusing and go from there. Dress for the party too, you know what I mean by that. That to me is only way to break the ice if you have a big case of the - " I'm not comfortable" on cold approaches. Parties are the best way, drinks flow, convo is easy and great music and people looking to enjoy each others company. Good luck, dude.

[TheEvilJester]

Start by participating in things that you are interested in. If you see women there then you have something in common to talk about. That's why I suggested that you join meetmarketadventures.com or meetup.com and pick an adventure that you like to do.

Get a dog... you will have women cold approaching you and your adorable puppy will help along the convo.

Yeah, I do need to find time to sit down and check out that website you mentioned. I’ve been busy enough, both in my work and personal life, that I haven’t had the motivation to do so, but I should check it out soon.

I would so LOVE to have a dog. Unfortunately, I work in the city and work a 9 to 5 type of job, so I feel like it wouldn’t be fair to Evil Barkington McJester because I wouldn’t be home enough. Dogs aren’t like cats. They aren’t as independent and need an owner who can be around more.

A stranger is just a potential friend you haven't gotten to know yet. You start out by just getting comfortable talking to people you've no reason to talk to and you build on it.



...or a niece or nephew. A friend's kidlette. Women often fawn over a guy with a youngling in tow and no matriarchal figure in the frame.

LOL! I think that is part of the problem, solarion. I am not comfortable talking to somebody I have no reason to talk to in the first place. I have always been too shy to make that effort. Without some kind of reason to strike up a conversation (an ice breaker, if you will) I just do not know how even to go about it. I know the idea is to just go for it and not overthink it, but the problem is that wouldn’t really work for me. I know myself well enough to know if I do that, I won’t know what to say and I’ll just look like an idiot, or at least wind up feeling like I look like an idiot. That, I actually know from experience. I need to have SOME idea of what the heck to actually. Then, if the conversation could actually get rolling, I actually have enough confidence in myself to trust I could do well, and actually seem funny and charming. It’s just I really have no clue how to even get things started. At least not unless there IS a natural ice breaker somehow, but these days I just don’t have those opportunities.

I also do not have a niece or nephew at this point. Not really any of my close enough friends have children either. So, no wee one I can borrow temporarily. LOL!

I think part of my problem, too, is I sort of don’t WANT to just meet somebody at random like that anyway. I don’t necessarily like the idea of just meeting somebody and, at that same moment saying “Hey, you want to go out some time?” I prefer to know somebody before I make that decision. Problem is, these days I no longer seem to have much of an opportunity for that, so it seems I am going to have to just learn to do this.

Got any party friends, you know the types ,they throw a big rager every weekend -- get yourself at one of those, there'll be girls a plenty around and you can chat up many and if you drink take a few for courage and just be friendly, amusing and go from there. Dress for the party too, you know what I mean by that. That to me is only way to break the ice if you have a big case of the - " I'm not comfortable" on cold approaches. Parties are the best way, drinks flow, convo is easy and great music and people looking to enjoy each others company. Good luck, dude.

Unfortunately, I’m not a big fan of parties. A) They just aren’t my scene. B) I don’t drink. Honestly, parties succeed only in making me feel MORE isolated. I do try, but I just wind up feeling like everybody talks to each other and I just go mostly ignored like I am not even there. Which I realize is, in large part, my fault. I don’t really know how to socialize well with complete strangers. I do at least make the effort because I don’t want to be one of those people who looks like they are completely miserable to be there and people wonder why they even bothered to come. I’m not a party pooper, it’s just not really my scene, so to speak.

I guess part of what has had me thinking about this lately is that, on occasion, I do see a girl or girls who seems interesting to me for one reason or another. I mean, I can’t even always necessarily explain why. For me, it isn’t just about attractiveness. It isn’t like I go around “falling in love” with every attractive girl I see. But, sometimes, for reasons even I can’t explain, a particular girl catches my eye for some reason and I find myself thinking “I would really like to talk to her and actually get to know her better.” But, those encounters I have these days are just with random women in places/situations that don’t really seem the most conducive to chatting up a complete stranger. Like the examples I’ve mentioned, the train isn’t really the best place, nor when I am at the gym do I really feel like talking to somebody. I just want to get in my workout and go home.

Anyways, I appreciate all advice I have been given, and any more that will come. Please do not misunderstand and think that I do not listen. I absolutely do, and 100% intend to do my best to put all your kind and thoughtful advice to use. I don’t know if I will be able to bring myself to actually do so, but I 100% intend to do so. It all seems so daunting, and sometimes I even wonder why I bother…. But I know if I never put in any effort, then I’ll never get over all of this.

Thank you again.

[megvoh]

Did you try to find any trivia or book clubs to join? Check meet up groups in your area?
What about mates who are busy on the social scene hooking you up with a girl to go out with, even if you don't match up you can practice the chat chat banter with them, same for any of your female friends with single gfs?
I'd prefer suggestion of IRL over OLD life to you. Least you get to see them for who they really are right off the mark.

[solarion]

LOL! I think that is part of the problem, solarion. I am not comfortable talking to somebody I have no reason to talk to in the first place. I have always been too shy to make that effort. Without some kind of reason to strike up a conversation (an ice breaker, if you will) I just do not know how even to go about it. I know the idea is to just go for it and not overthink it, but the problem is that wouldn’t really work for me. I know myself well enough to know if I do that, I won’t know what to say and I’ll just look like an idiot, or at least wind up feeling like I look like an idiot.

You start by pushing the boundaries of your own comfort zone. You have to overcome your fears and just do it. I'm not talking about just prancing up to a hot chick in the produce section here, start small. Just make idle chit chat with some guy walking his poodle at the park. Chat it up with the bagger at the grocery store...the cashier. The point is to get used to initiating conversations so that you gain the confidence to approach anyone. Eventually worrying about saying something silly and not saying anything, will become a distant memory and even if you do say something that's off the wall, you'll learn to quickly cover it with some self-deprecating humor or tactful subject change. You have to practice these things to get better at them though.

[TheEvilJester]

Did you try to find any trivia or book clubs to join? Check meet up groups in your area?
What about mates who are busy on the social scene hooking you up with a girl to go out with, even if you don't match up you can practice the chat chat banter with them, same for any of your female friends with single gfs?
I'd prefer suggestion of IRL over OLD life to you. Least you get to see them for who they really are right off the mark.

Unfortunately, like the web site Wakeup mentioned, I've been too busy to look for stuff like that so far. Actually, to be honest, I don't even know how to go about starting to look for stuff like that.

All the same, I do hope to motivate myself to check that out soon. The thing is, though, I don't worry so much about that. That sort of thing gives me a ready made ice breaker, so to speak. Not to mention, you get acquainted with each of the group members in more of a group setting, so it isn't like they are COMPLETE strangers. I think both your suggestion and Wakeup's would be a great idea for me.

Though, that isn't exactly what I am talking about in this case. Again, because in a case like that it gives me the in already, and I'm much more confident (these days anyway) that I could actually at least give it a shot with that kind of an in already in place. My bigger issue is when you don't really have that in. Like, for example, when somebody at random catches your eye, how to actually approach and talk to them. Or when there is somebody specific who you see often enough to be interested in getting to know them better, but maybe it is a situation where you don't really socialize with one another, so you are just basically passing strangers. You know, that whole "she doesn't even know I exist" kind of scenario. LOL! Those are the things I don't necessarily know how to handle.

But, these days it feels like maybe I should. I mean, I definitely do think meeting somebody at a book club or something like that would suit me so much better, but people don't necessarily go to stuff like that looking to find somebody to date. Just as much of a chance that I'd not really meet any dating prospects there either. Hence why, in part, I have begun to think maybe I really should learn to take a chance with some of these chance encounters.

You start by pushing the boundaries of your own comfort zone. You have to overcome your fears and just do it. I'm not talking about just prancing up to a hot chick in the produce section here, start small. Just make idle chit chat with some guy walking his poodle at the park. Chat it up with the bagger at the grocery store...the cashier. The point is to get used to initiating conversations so that you gain the confidence to approach anyone. Eventually worrying about saying something silly and not saying anything, will become a distant memory and even if you do say something that's off the wall, you'll learn to quickly cover it with some self-deprecating humor or tactful subject change. You have to practice these things to get better at them though.

Yeah, I kind of do think the only real solution is to learn through practice. I agree with you on that. I do, 100% full intend to try my best. It's just very daunting for somebody like me. It sounds like such a simple thing. You'd think it would just be as simple as that. Just go for it and it will get easier in time. But, I'm 32 and have lived that way my entire life. In fact, for most of my life it didn't even occur to me that anything was weird about that, or that I needed to change it.

I've overcome so much, so it isn't like I can't overcome this. I just don't even know how to motivate myself to begin. It doesn't help that I was born such a romantic. I hate it. It seems if I am not in a relationship at the time, I've always got a crush on somebody. Don't get me wrong. I'm not as bad as some people. It isn't like I get a crush on any and every woman I see (and I am also very realistic about my crushes). Still, there tends to be somebody who (most often for reasons even I cannot explain) catches my eye enough that I feel like I want to get to know her better to determine if maybe I would like to ask her out. Despite that, I've never had the tools/understanding for how to do anything about it.

Anyway, my point being it may seem ridiculously simple (because really it SHOULD be), but for me it might as well be speaking another language without ever having a lesson. All that said, I'm not giving up. I do intend to give it my best. I don't know if I can motivate myself to do so, but I definitely mean to try.