Deano’s answer to: “How can one tell if a women is flirting because she is really interested in a man or she is just leading him on?”

The biggest mistake this question makes is assuming that flirtation itself is a medium used to communicate interest.

Flirting is, and has been throughout history, more of a recreational mind-sport, and a way to give your fellow human beings the occasional ego boost to get them through their day. Everyone loves feeling attractive, and merely pointing out attractiveness should never be taken for more than that.

That all said, flirtation is often an opening indicator of interest in the US these days, primarily due to the proportionately higher chances that it will be mistaken for direct attraction… There are fewer and fewer playful flirters on the social scene these days – it's turning into a very rare breed indeed.

My overall advice on dealing with flirtation is simple: get thee to a flirtery! If you can't find an intro to flirting class nearby (there are tons of them in the San Francisco bay area, but I imagine it's not as common in, say, Idaho), or spend a few solid months living in the cultured deep South or Western Europe, then I recommend trying the following exercise:

For the next 30 days, every day, when you notice (not just see, but notice) someone, compliment them. Don't go overboard, or have too much intent for it to go further. Even just saying that someone has cool shoes, or a interesting hairstyle/accent/handbag/iPhone app is enough.

I recommend striving for at least 5 per day… The first week, feel free to include friends and family, but focus on strangers only from the second week onwards.

By the end of the month, you should be able to confidenty compliment everyone you see, even hundreds of people per day if need be, and your compliments will be seen as genuine. In truth, they probably will be, because you'll be far more observant of the world around you than you were before, and a lot less desperate for a particular response to your most casual of flirtations.

With that amount of skill and experience, it should be very easy for you to "flirt back" in response to an opening flirtation, and easily gauge whether you are merely playing a game of "compliment badminton", or if she's genuinely interested in taking things to the "Starbucks awkward coffee date" level with you. 😉

If you can't wait a full month, and you can check your pride, assumptions, and violent heterosexual rage, you can gain a similar amount of experience in around a week if you focus your efforts in local gay bars. 🙂

How can one tell if a women is flirting because she is really interested in a man or she is just leading him on?

Deano’s answer to: “Do men feel cheated when a woman wears an extra padded bra, to the point where her breasts appear one or more cup sizes larger than reality? Why or why not?”

I would say no, because by the time I'm finding out, there are usually other compensating factors already at work to balance out the deception.

Do men feel cheated when a woman wears an extra padded bra, to the point where her breasts appear one or more cup sizes larger than reality? Why or why not?

Deano’s answer to: “Is it better to be skinny and ugly or fat and cute?”

As Amy Quispe states, the answer is basically buried in the question, though I'll go a bit deeper:

  • Ugly, by definition, is not tied to a particular body shape or size
  • Cute, by definition, is also not tied to a particular body shape or size
  • Predictive level of health status and issues, however, do come closer to mapping to a specific range of body sizes – too skinny is seen as unhealthy, as is too fat

I think that, casting direct issues of anorexia, obesity, predisposition to diabetes and the like aside, what it comes down to is this: attractiveness is based primarily on what you DO with what you've GOT.

For example, I go to Japan fairly regularly… And I'm always reminded not only of how much generally larger American women are in the strictest sense, but also in how much cuter the average fat Japanese girl is, compared to her American counterpart. This isn't a case of "Yellow Fever", but rather an observation that women in Japan, regardless of their body type, seem to have a much broader and better understanding of how to make their particular legs/hair/physique work in combination with the fashion, makeup, and beauty regimen they can afford. I hate to be this blunt and overgeneralize at the same time, but it seems to me that a lot of the time, if an American woman feels she can't be one of the most beautiful women in the room, that she tends to scoff at the very idea of striving to be beautiful – turning her defensiveness and anxiety about her looks into a more "respectable" pseudofeminist political statement.

This is definitely not something women do on their own – a lot of the western fashion/beauty industry caters to a very small subset of females… If the latest dresses aren't flattering on you, you'll quickly find that the much better stuff from last year's collections have all but disappeared. This doesn't seem as prevalent a force in non-Western countries. In Japan especially, every single fashion fad that every was, lives on today and probably will continue to exist far into the future.

In short, whether you are skinny or fat, or anywhere in between, being cute (or ugly) is mostly up to you. If you want my advice, I'd suggest trying to find the cute that works for you, and the people who find that attractive… And spend a lot less time worrying about small-minded detractors in the world at large.

Is it better to be skinny and ugly or fat and cute?

Deano’s answer to: “How do girls feel about it when guys pursue more than one girl at a time?”

The idea of pursuit makes me imagine men running around with flashing red and blue lights in their pants.

That said, in terms of cultivating multiple relationships with women, some of which are intentionally non-platonic, need not be harmful, rude, or otherwise "bad". In fact, by showing the disconnect between interest and possessiveness/constraint, such men often are seen as more desirable. The same is also true of women – and it's not a strictly heterosexual phenomenon, for that matter.

Whoever you are, whatever your preferences may be, by showing a matter-of-factness in your interest in another that does not single them out too soon, you're showing maturity and comfort in your own sexuality and romantic relationships generally. This is, for the most part, a good thing – though the number of people who do this in a self-aware manner, with an equally self-aware partner are few and far between.

As with all relationship matters, rather than looking at the situation you perceive and filling in the rest with assumptions, it's best to express your feelings, and genuinely listen to what your partner/prospect has to say – and hopefully, move forward together in a manner that promotes mutual enjoyment and communication.

How do girls feel about it when guys pursue more than one girl at a time?