[LeoJ]

I am a 5'11" slim guy, and throughout my life, I’ve often felt seen as one of the "most good-looking guys" in my social circles.
I guess I got used to that idea, and built a lot of my self-image around it.

Because of this, I remember feeling really uncomfortable back in high school a few years ago when a girl told me that one of my friends - who seemed to be on the same level as me in terms of looks, and got the same amount of attention as I did - was more good-looking than I was.
I am not sure if she meant it seriously or was teasing, but it bothered me a lot.

Now at university before the summer holidays, I ended up in a class with a 6'9" tall, very muscular man who draws effortless attention from girls.
It is pretty obvious from their flirting and frequent attempts to spend time with him that he is considered far more attractive than not just me, but most guys around.
At first, this made me feel really uneasy, since I have never felt this overshadowed by another man before, and it affected my self-image a lot.

A few girls from the class noticed this in me and kindly reassured me that I look great, but they also firmly admitted that this guy is considered "much more good-looking" than me by themselves, and apparently also by most others.

...and surprisingly enough, I felt totally fine hearing that.

This kind of direct comparison would normally make me feel anxious, but somehow, in this case, it didn't;
it actually felt perfectly fine, even though I know that I would still generally be very sensitive to potential comparisons like that.

How does this work?
Shouldn't I feel even more uncomfortable being told so clearly that someone is considered "far more attractive" than me, especially when I was told this by several girls this time, and also the fact that I reacted uncomfortably to that comparison in the past?

[Tart Cherry Jam]

I don't know how it works, but you dodged a bullet (within yourself, within your own reactions) and deserve to celebrate it.

Do read the absolutely riveting, gripping short story "The Shot" by Alexander Pushkin (the greatest Russian author), about what would have happened to you had you NOT in the end felt fine hearing that the girls preferred that other man to you in terms of looks, AND had you lived in the early 19th century Russia.

Oh, and "dodged a bullet" would acquire a literal meaning once you have read the story (just make sure to read the story itself and not some Wikipedia article about it which would break the suspense for you).

[LeoJ]

I guess that that is roughly how I feel;
it just seemed funny at first how I was sensitive to even the thought of these comparisons, and yes without any discomfort could hear that this man wasn"way more good-looking".

[divine1966]

I find it rather strange than these women (I assume they are adults) literally compare who looks better and make their opinion known. Rude and shallow.

Perhaps you aren’t bothered by it because you grew up. Not too many adults are bothered doing these “looks comparisons” of themselves or of other people

[Tart Cherry Jam]

Originally Posted by LeoJ

I guess that that is roughly how I feel;
it just seemed funny at first how I was sensitive to even the thought of these comparisons, and yes without any discomfort could hear that this man wasn"way more good-looking".

I have reread your OP and the one difference I spotted on a second, more careful reading is that the first comparison might have been made in a teasing way, with the intention to provoke insecurity in you, while the second comparison was preceded with reassuring comments that you do look great. Maybe that difference in the intent of the commentary mapped into the difference in your response to it. Maybe you are not entirely correct when you state that you are sensitive to comparisons–perhaps instead, you are sensitive to teasing comments.

Another difference, as mentioned above, is that you are now in college, more mature than you were in high school, and that maturation might have made you impervious to direct comparison.

You mentioned that that other guy is much taller and more muscular than you are. These dimensions of looks are easily quantifiable, but there is more to appearance that is subjective and escapes such direct quantification with a literal yardstick. I imagine that there are girls who find your face more appealing and there are girls who find his face more appealing.

Lastly, I am unclear how you arrived at the use of the term "usually" in the OP's title if you only have two datapoints. And in only on of them, you exhibited sensitivity. One is not enough to say that you are usually sensitive. Or were there more datapoints that you omitted for the sake of brevity?