Nothing to lose as dmcreif said. He had nothing but an upside from his point of view. Either she says "yay" and they start going out again, or she runs from the situation and he is where he is now anyway.
He has known Karen now for a couple years and he knows she won't ever tell anyone.
It occurred to me that Matt thinks Karen might be more predisposed to accept of him being Daredevil than Foggy was.
The first reason I think Karen would be more accepting and forgiving of Matt for being Daredevil is because unlike Foggy, she's personally seen Matt in action as Daredevil. That's a big difference. To Foggy, Matt's actions as Daredevil exist in the abstract, as stories and images that play on the evening news. He has no connection to anything in the other half of Matt's life. He doesn't see Matt out there getting beaten up and chasing down Kitchen Irishmen, Hand ninjas, or Dogs of Hell bikers. But to Karen, Matt's actions as Daredevil aren't in the abstract or something that you hear about on the evening news, because she's actually seen him in action. She knows that in recovering the USB with the Union Allied pension file, she'd be dead if Matt hadn't shown up and subdued Wilson Fisk's hitman. She also personally saw Matt engaging the Hand ninjas who were holding her and the others captive, the same ninjas who were about to amputate Turk's foot.
The second thing I point out is a specific scene. It's when Karen visits Matt at his apartment after the hospital shooting in "Dogs to a Gunfight". First, she admits she is barely holding it together and doesn't like being used for target practice. In the same conversation, there's this exchange:
Karen Page: Sometimes I worry about you a little too much.
Matt Murdock: I appreciate it. There's no need to worry.
Karen Page: Yeah, you know that doesn't help, right? You denying that there's anything wrong?
Matt Murdock: Karen-
Karen Page: No, how many times can I hear that you "fell down the stairs" or you "walked into a door"?
Matt Murdock: Well, you know I'm blind-
Karen Page: And you know that I'm not an idiot. [beat] Okay, um, let's say this: when or if you ever feel like you can tell me what's going on with you, I promise that I'm here. Is that a deal?
Matt Murdock: That is a deal.
I bolded that line because that's a very telling line in hindsight. It means Karen is willing to hear Matt out if he decides to admit what's going on with him. I think Matt took Karen's advice and that line in particular, when admitting his identity to her.
And then there's the rest of that conversation: Karen then admits to Matt that she feels the Punisher was inevitable after the public began cheering on Daredevil and her voice seems to break a few times while she's talking. It seems like she didn't want to admit these things while in Foggy's presence.
Third, I point to Karen's insistence on pursuing justice to the very end, first when taking down Wilson Fisk, and later when she insists that they look into the Punisher getting shot and Reyes being involved in the cover-up, even after Foggy begs her to let it go. We know that Karen is a very determined individual, and refuses to let go of an investigation no matter how many other people try to convince her otherwise, no matter how many times they get put in danger, and no matter the personal cost on those around them. Matt seems to be one of the few to actively support Karen's determination, probably because he realizes she's just like him: he refuses to let go of his pursuits of Fisk, the Punisher, or the Hand even when this gets him regularly injured, destroys his friendship with Foggy, gets Nelson & Murdock shuttered, or gets Elektra killed. So in Matt's eyes, he and Karen are very alike in their determination to get justice for those the system has failed, the only difference being that Karen doesn't have Stick's training. They also have a tendency to keep secrets from those they trust; Matt's been keeping Karen in the dark about his...ahem, dark passenger, while she's keeping secrets from Matt and Foggy like the fact that she killed James Wesley. There's also the two having a tendency to lie about major or minor things, Matt when it comes to Daredevil, while with Karen, she claims Tower slipped her the files when she actually stole them, or claims that Frank Castle kidnapped her when she really ran off with him.
Fourth, there's Karen's conversation with Castle at the diner in ".380". She admits that she's got complicated feelings for Matt, and Castle gives her some blunt relationship advice that, in theory, might rub off on her just enough that she's willing to give Matt a second chance.
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