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Hi Lights, how are you doing? I have to say you sound like quite a brave man! Asking strangers out in a fleeting interaction? Takes guts.

Thanks, Kamille. :) I'm good. How've you been?

 

A few comments. First, Tarnbak is giving great advice. The first thing you do want to do is put 'her' at ease. Be a perfect gentleman without falling into 'desperate'. It is your responsibility to make the interaction fun for her. You are, in other words, offering her something.

All right. What would do that, though? That's why I tried to come up with specific methods of asking in earlier posts.

 

Second, recognize or create opportunity. In my city, it is way easier to interact with strangers in certain neighbourhoods (for me it's generally the artsy neighbourhoods - Toronto: Kensington market, Queen W.) late friday afternoon then at any other time.

Okay. I haven't really been able to select the areas I was in when someone passed by, but I suppose this is definitely applicable if I do go out looking specifically to meet. Thanks, Kamille.

but Kensington is a touch granola for my taste.

What does this mean?

 

Your description of what you're looking for and how you perceive your city made me think that what you need is a trip. I don't know how old you are but it seems to me that the kind of encounter you are craving happens most often in the european backpacking circuit.

 

Take a trip and hopefully you can regain some confidence. If it works you may even consider moving.

 

Totally. I should take a trip out of here, and eventually move. The parts of the culture that are accessible to me have sickened me for years on end, and things haven't ever really improved. I'm 27. I've never gone backpacking anywhere before, but I'm considering fitting some of that in it once I get a better idea of how my career and job path should go.

 

last, a question... Why is it important to you to be able to pick up strangers? What are you looking for? Someone to share your life with or flings? Because, if the first, then studies have shown that you are most likely to meet the right person in your own networks. In this case, what you want to do, if your networks are perticularly devoid of interesting women, is create opportunity by joining new groups - making new friends, etc.

Well, either/or or neither/nor, really. My life is a bit strange (at least compared to what many others expect) in that I don't get to know ahead of time whether there will be women I might be interested in nearby in the next places I might be in while I have free time. So to me, if a fling or a life partner or anything in between happens, it happens.

 

It's not that I'm necessarily bent on picking up specifically a stranger, but rather that I'm aware that oftentimes it might be the situation where I might happen to be. (It's not unlike seeing a possible cutie in the gym when one's own time-schedule there is erratic; not only don't you know if you can count on seeing them again, but there are also the issues of needing to return to what you are doing once your rest period ends, of one or the other not being able to converse that effectively through a set of deadlifts, and of not knowing whether or when they'll simply vanish.)

 

Ideally I'd join new groups that have more more interesting women and dedicate significant time to that and happen to meet them exactly at moments that are perfect for both of us, but in practice I can't control how many attractive/interesting women are around nor allocate too much more time to avocational stuff. But even then, in more conventional cases I'd use longer, more conventional approaches.

 

I'm just asking about a specialized situation that just seems to happen occasionally in my life.

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