I <3 Maisie, first of all. A quick look at her profile makes it seem like she'd definitely be the sort who's clever enough to see through his bulls^&t, maybe? He needs people who do. He's both flustered by, and has huge respect for them. If they happen to also be blundering do-gooders with handcuffs? Not so much. But never mind. His loop is almost completely undefined at the moment so I don't have any specific instances to offer where she might throw a wrench in the works, but I'm always happy to work stuff out down the line. Or whenever.
Oh? Care to share more about her? It could be fun to twine some of their bullet points together. If she's got any money, he'd be on that like flies on honey. Actually, if she's just a pretty thing with a complete and utter lack of money and seems a little vulnerable, he would be anyway. Just not in an alternative motive kind of way. He's utter dishonest occupationally, but he does have a heart in there. Maybe it's just a bit of a disillusioned self-portrayal as a bit of a Robin Hood that still peaks out now and then.