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I had no idea this was a boy's name! You learn something every day. :)
I guess it would be fine if you lived in a place where there were quite a few of them, but otherwise, the confusion with Kristin and Kirsten is probably going to be uncomfortable for him.

I don't like cross-gendered names, and it would hypocritical to deny that, for most people, a female name on a boy is going to be more awkward than a male name on a girl.

no... wouldn't do it...

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Kristen's a pretty name... emphasis on PRETTY... about as girly as you can get... Doesn't belong on a boy at all.

I like it in theory, but it's one I wouldn't use in real life most likely. (Unless I were in another country where the name was very uncommon so the association with females wasn't so strong.)
I do really like the charm of it on a boy though.

From experience...

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It's a nice name in theory, but doesn't really work. I know a guy named Kristen personally and his name has been a bit of a sore spot for him. He prefers going by Kris when he can, and he's gotten made fun of a bit...mostly in jest from his friends, but still enough that he's not fond of his name at all.

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Christian or even Kristian would be a better idea and less likely to cause problems. Even though there are a lot of little girl Averys and Finleys running around, gender swapping doesn't really work both ways and it is difficult for a boy to have a "girly" name even though a girl can bear a masculine one. Keep Kristen on the GP list, that's my advice.

I don't mind it. My male friend is named Kristen so I am already used to it. He goes by Kris most of the time.

personally, I dislike it a lot. It's just so feminine in my opinion

I don't think it's that bad, but I think a different spelling might be in order. Christen, maybe?

Are you pronouncing it like Kristen or Kristian. I think Kristian is fine for a boy, but not Kristen. It's much too feminine.

Well, since I like a few boys' names on girls, I would be a hypocrite if I said Kristen on a boy would be bad. It actually sounds more masculine when you think about it, and I've heard they use it for boys in Nordic countries. I'm not sure if it would fly in the US, though.

I actually know a guy named Kristinn- he's from Iceland. I wouldn't use on a boy anywhere Kristen is used as a girl name. In Iceland, Kristinn is masculine and Kristín is feminine, and I met him in Spain where Kristin in any spelling, male or female, is basically unheard of.
My birth name is Kristin... I feel like Kristinn suits my friend better than it suits me.