Otherwise, I don’t know how this happened, but I’m not that used to being underestimated, and I don’t think I’m particularly arrogant; I very much dislike having to self-promote, and writing personal statements to get into grad school was torture.
I have a short temper, and get exceedingly pissed off when people condescend to me, but there are always occasions where it’s better to shut up and smile. And it’s infuriating.

It is a quandary indeed: I struggle daily to break out of the polite, unassuming behaviors ingrained in me and assert myself more. But I also don’t want to become that unappealingly arrogant. So I continue to seek that balance, and I believe there are many female role models surrounding us who stand up for themselves and their ideals without degrading into overconfident posers.

Pilgrim Soul, I do know where you’re coming from – sometimes people’s unawareness of their own limitations is breathtaking. And men are more commonly affected. But I do wonder whether this is really a situation where you have to be a bitch – no-one likes to have their faults pointed out to them, and unless someone asked me to point theirs out, I probably wouldn’t. (Although I also try not to give false praise…)

PS – I don’t know how you feel about this and it certainly depends on the dynamics of your friendship, but would it make a difference to write your friend an email laying out what made you uncomfortable about the conversation? I don’t tend to do well with responding to situations like this as they’re happening, but I have had success with hashing things out post-convo in written form. Because really, this isn’t just about some lack of confidence or whatever on your part; it’s also about the way men are socialized to be bulls in the china shop when it comes to blasting their own horns. Just as many women (myself included) could benefit from a dose of confident bombast, many men could benefit from a push in the other direction. It’s about achieving a balance for both sexes.

(Which isn’t to say you have some responsibility to educate him – you don’t. But if it might help him be less of a dick in the future, and help you get some of this off your chest, it may be worth a shot.)

I think this is also a matter of gendered social conditioning. For men, if they do one thing wrong and 99 things right, that one wrong thing is often seen as isolated incident, an anomaly. For women in the same scenario, that one wrong thing somehow ends up largely invalidating the 99 right things in our own minds, and too often in the minds of others as well. We’re taught that we have to be perfect, polite, nurturing, quiet, etc. The idea persists that women don’t “naturally” belong in certain spheres; and there are still plenty of men who want to maintain the status quo, or, at the least, have been so thoroughly saturated with the Kool Aid that they just believe this idea without much question. These men tend to point to every little misstep a woman makes as “proof” that women can’t hack it in positions of power and prestige (in other words, as proof of their own natural superiority).

In theory, I think that confident bombast (based on the many things we do right) can co-exist peacefully in women with an openness to being wrong (because we’re all wrong on occasion). It’s just hard to achieve that balance given the above.

I’ve definitely had moments where I completely failed to Be A Bitch because I was stunned into silence by the complete confidence with which people spewed utter dick-itude. (After all, I went to school in the South with a whole lotta Christian evangelicals.) And yes, it was often dick-itude spewed by jackass, overconfident white men who’d read too much Ayn Rand.

We’ve all had those moments where we come up with the classic Dorothy Parker-like rejoinder, hours after the conversation’s ended. I am STILL coming up with the perfect retort to conversations I had 10 years ago with a former boss who overconfidently talked out his ass all the time. It really does get under one’s skin, and I completely agree that it’s WAY more of a male thing, because being a pompous blowhard is nearly always a male privilege.

The problem isn’t just men like this, it’s that they’ve structured so many business models to assume that if you’re not also manically egotistical, it must be because you’re deficient.