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I'm a Spanish 26 year old guy. I have the appearance of what people would call "loser good guy", so when I'm hanging out (mainly at night clubs) it's really frequent people ask out for a cigarette (especially girls who make it pretty clear they are not trying to flirt, but just obtain a free cigarette). Personally, I only like to give one either if I just feel like it or if the person is willing to stay and chat and has an honest interest in building some interpersonal communication.

Yesterday, a girl asked me if I could give one to her. I said no, so she started looking at me with sad face trying to be cute (which she was). I find this behavior highly manipulative, and that it may work with people that think that girls are machines where you insert compliments/gifts and it returns sex, but not with me, and honestly I find it highly offensive. To me, it sounds like they're trying to outsmart me and I would like to tell that person something like:

Hey, this might work with some losers who seek to get laid at any price, but not with me.

How can say to someone that I'm willing to share as long as he/she's willing to do some conversation without sounding too snobbish?

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If what you are looking for is that such people engage in conversation, why not use their sad-face/pleading as a jumping off point for that conversation yourself? Instead of saying 'That might work with some losers....', why not say something like

Does that usually work for you?

There are two ways it can go from there, either they will be puzzled and you can can carry on with something along the lines of

You know... that sad face thing. Does that usually make guys give you stuff for free?

Then they know that you understand their tactic. If you say these things with a smile and/or a raised eyebrow or a light laugh, rather than as a strong challenge then they might well make some sort of 'you got me...' response which can lead into enough of an exchange for you to offer them the cigarette quite naturally to prolong it.

...or they might not respond in that way, in which case you are no worse off than you were before and that person is less likely to ask you again.

If you avoid calling people who do fall for the sad-face routine 'losers', or otherwise insulting them, they you should successfully avoid sounding snobbish.

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As some other answers mention, it's easy enough to get a conversation in exchange for a cigarette: just be straight forward "I will trade one cigarette for one conversation". It seems, however, that you want the other person to actually be interested in the conversation, and not treat the conversation as a requirement, chore, or something that can be beaten. If you want the stranger to be interested in a conversation, the onus is on you to be interesting.

There is no general answer to what people find interesting, so you'll have to do some work. Luckily, this stranger, let's call them Jessie, already let you know something they are interested in, your cigarette. So, start with something you know will interest them; immediately agree to give Jessie a cigarette, but also start a further conversation with them. Before actually handing Jessie the cigarette, perhaps while taking it out, ask them questions to try to find something that interest them. After you find something that both you and Jessie are interested in, and exchange a few lines about it, hand them the cigarette, preferably while asking another question. More than likely, Jessie will stay around for a bit. After all, you are in the middle of a conversation that they are interested in.

Of course, this won't always work. Jessie might be in a hurry, or they might exit the conversation as soon as you hand over the cigarette. In particular, if you just can't find anything that seems to interest Jessie in a reasonably amount of time, hand them the cigarette anyway, and let them walk away if they choose to. Don't fret when it doesn't work; you haven't lost anything but a cigarette, which should easily be offset in the long run by the mutually interesting conversations you do have.

Finally, an example of how a (successful) conversation might go:

Jessie: Hey, do you happen to have an extra cigarette?

You: Of course, but humor me for a minute. (Begin taking out cigarette) Have you seen any good movies lately?

Jessie: No, not really.

You: Are you reading any good books?

Jessie: No.

You: (Holding requested cigarette in hand) Well, are there any bands you like?

Jessie: I'm pretty in to A Perfect Circle.

You: Really? Me too. (While handing cigarette) Are you hyped for the new album? What do you think of the new songs?

Jessie: (Takes cigarette) Yeah, of course. Disillusioned is pretty amazing!

You: Need a light?

Jessie: Yeah.

You: (While getting out lighter) I really like the influence Puscifer's sound seems to have had on Disillusioned. I think it works really well with the rest of APC's style.

...

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How can say to someone that I'm willing to share as long as he/she's willing to do some conversation without sounding too snobbish?

Honestly you really can't and you seem to be misunderstanding the usual etiquette of asking for cigarettes...

Someone asking for a cigarette isn't obligated to entertain you with conversation and most certainly isn't obligated to flirt or accept advances. Generally it's an unspoken rule that you get what you give. Smokers know what it's like to run out at an inopportune time, have empathy because they've been in that situation and help each other out when they can. That's about it.

If you want to strike up a conversation, strike up a conversation, but this should be entirely separate from being generous enough to provide someone with a cigarette. It shouldn't be transactional. Making it transactional is very likely to backfire and lead people to think that you're manipulative, stingy, or just plain rude. People don't respond well to being taken hostage, or purchased in social interactions.

I'm not saying that you are obligated to give all of your cigarettes away; I'm saying that giving one or two away here and there is an act of charity. Do it as a charitable act, with some empathy, or don't bother.

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Don't pass judgement on their request, or their methodology. That's a dick move.

It's important to remember that by changing from you giving them cigarette to you trading a cigarette for conversation you are changing the nature of the relationship. You will be re-framing the interaction from one between friends or at least friendly strangers, to a transactional one.

In the US there's an unspoken expectation that if someone asks for a smoke they're going to light it up then and there. This leaves plenty of room for conversation as you're finishing your own.

If you feel like insisting on a transactional relationship is the correct approach, be clear about your intentions. Say something like:

Only if you want to talk while I finish mine.

This makes it clear that this relationship is transactional and exactly what you are expecting in return for your cigarette.

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I've very rarely bummed cigarettes. However, the thing is, if I do bum a cigarette, I feel like I'm already importuning somebody and the politest possible thing I can do is not bother them any further.

But if I asked someone if he had a cigarette to spare, and he said something as simple as, "Sure, want to hang out and chat with me while we smoke," that would change the whole dynamic, and unless I had some pressing need to hurry, I'd probably find it charming and happily stick around, as long as it seemed casual.

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Yesterday a girl asked me if I could give one to her. I said no, so she started looking at me with sad face trying to be cute (which she was)

If she expects to snap her fingers and get free stuff just because she exists, this is because it usually works. So, what can you do?

  • Give her a cig. You gain nothing (don't expect any gratitude), you lose a cig.
  • Tell her off: It's cheaper, but you'll have to be rude, and you'll sound like a cheap whiner, so you lose at least one pride point, with +1 extra per girl who overhears, +10 if she comes out with a witty retort, and +100 if you cave in and end up giving her the cig.
  • Enter a commercial agreement (as other answers propose): Problem is, she's probably heard it already, she came for a free cig, you have three seconds to make a sale, and she's not interested, so she won't listen to anything longer than 10 words. So this won't work either.

So, just flip the script, by saying something preposterous that nukes her expectations. Worst case, she runs off, best case she laughs.

"Hey, you look cute like that, wanna buy me a drink?"

In other words, the mere notion that you would give her anything (except some of your attention) in exchange for being in her presence is so alien to you that what she said didn't even register. You're not here to make a trade or commerce with her like the other answers suggest. Also, you're not whining that she tried to get a free smoke out of you. You just ignore it, which disarms the budding confrontation. If she looks really sad, you can also try:

"Need a shoulder to cry on?"

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You don't need to promise them anything or provide any conditions on which they might get cigarette.

If someone comes to you and asks, do whatever your heart tells you at that moment. If you think that person simply wants to get a free cigarette, just say "I am sorry" then smile at them (I mean sincere smile). Don't be rude to them, and don't explain anything, just see how they react.

If someone reacts harshly or gets angry then I wouldn't want to give that person cigarette anyways. If the girl becomes manipulative, just stand your ground and talk to her, joke around, etc.

Finally, you will learn to weed out people who are honest, open and don't come to you only to get free stuff. To those people you can give cigarette if you want.

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If you want them to earn the cigarette with conversation, start the conversation. Smile, uncross your arms, reach for your pack, and say

What's in it for me?

Make sure it doesn't sound sarcastic. If you default to sarcasm for a sentence like this, you might want to practice in a mirror or try other phases like

Are you sure? There's a price. Ok, but not for free.

Either way, this is a fairly open ended question. She may be offended, amused, or interested. Either way, it's an opening for her to engage with you and not your smokes. It's likely she doesn't get this challenge often, so she may reply

What do you want?

From here, you can tell her what you want.

Honestly, I'd just be happy with some conversation while we smoke. I'd appreciate the company. [reach out to her with the cigarette, keeping it kind of close to you] Have you been to this club before?/Have you read any good books/Do you watch {TV Show}?

At this point she can decide if she wants to to reach into your space and take the cigarette and stay, take it and go (stealing it, given that you've named your price), or not take it and just go. 2 of those 3 scenarios are in your favor (you get company or keep your cigarette), so the outcomes are in your favor.

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I think your best bet would simply be to say "no" to the request, since I think it would be improbably difficult to negotiate a trade of conversation for a cigarette without it being awkward or unenjoyable. Forcing someone to talk to you in trade for a smoke seems like it would be unpleasant to me. I can't imagine you'd get any good conversation from anyone under those terms.

Maybe if someone comes up to you and strikes up a conversation first, then asks later on you could modify your response to a "yes". But otherwise probably your best bet is probably to stick with "no" and ignore the puppy dog eyes, cute or not.

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