I liked 19 and 12. I wonder if it wouldn’t be good to have a non-smiling photo? One where you look more serious or pensive, even.
The last three because I have that sweater, too.
What?
Thanks to everyone who responded (and especially to Shayna for tallying the votes)! The input has been very helpful, and has made me feel less insecure about whether or not I photograph well.
I’m a little surprised by the unanimity of opinion regarding solo shots versus group photos, since when I look at profiles, I always appreciate seeing pictures of the girl out and about with friends and in other social settings. But I’m definitely being careful to strike what seems like a good balance in my own pictures.
I’d already tentatively selected 28 as my main picture before starting this thread, so I’m glad to see that my opinion on that was justified.
I’m also surprised that the dressier shots (3-16) got so little love, since I like to think I clean up nice. 
(Also, my hair, which is often troublesome, is less troublesome in those photos than in some of the others.)
don’t ask:
The irredeemable doofus in me is exactly what I’m trying to avoid revealing until at least the second date.
The thing about the dressier shots is that the specific clothing doesn’t photograph well - not enough contrast after 8. 3-8 are fine but for an online dating picture it’s best to have you by yourself.
And girls love guys with dogs.
ETA - never knew you were a hottie, man.
Pfft! What do you think I’ve been trying to tell people for the last nine years?
(Also: NINE YEARS? Oh, mercy.)
(1) List your five favorites, with any comments you might have
19, 20, 30, 3 (if that’s your mom and dad), 12
I chose the first three because they’re solos and the last two because you look like you’re having fun.
(2) List three (or more) that you definitely wouldn’t use if you were me
25, 24 - pictures of yourself with women hanging off you on a dating site probably aren’t a great choice.
(3) Give me feedback on especially flattering or unflattering aspects of different pictures (feel free to be brutal)
Most of them are very flattering. You have a very nice smile and look happy and relaxed. None of them are overly posed. I didn’t see any that were very unflattering.
(4) Tell me which picture you’d choose as my primary photo, which will be the first one that someone sees when they look at my profile
My money is on 19 but that’s because I like outdoorsy folks.
(5) Suggest crops or edits that would make particular pictures look much better
N/A
I’ve voted for 19 and 20 in the top five because you’re alone. I don’t think you should choose photos where you’re competing with other people (either guys or a flock of women).
I’ve not enough patience to examine all your pictures, but like many other posters, I think there are too much group pictures to choose from, and not enough solo pictures. I would especially avoid the pictures were you’re standing alone with another person, like 4 and 9 to 12.
Also, I think the 19 is great and should be included, even though I don’t think it should be your primary photo.
More nudes please.
First, you are indeed a hottie. You take a good picture and have an open, friendly smile, too. I agree with everyone else who said dating profile pics should be of YOU alone. You don’t want the ladies looking at pictures of other ladies and ruling you out because you don’t know enough not to post pictures of yourself with other girls, and you don’t want the ladies looking at pictures of you with other guys and thinking the other guy is hotter!
I liked 19, 27, 28, and 30 the best (yeah, your hair is too goofy in 20 - you need a haircut, son). I think I would choose 28 as your profile pic - I think it represents you in the best, most informative way.
ETA: Oh yeah, more nudes! 