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I am a German citizen currently in Canada on a working holiday visa valid for 12 months from last year's September. My fiancé lives in the US, and I visited him for one week in February and another 2 weeks last month. My visa waiver expired on the day I went back to Canada, but I would very much like to return to the US at least for another 1 or 2 weeks this June before I go back to Germany in July. However, I am not sure if I am eligible for another visa waiver, seeing as I haven't returned to my home country in the meantime – could I be an exception though, considering I have a work permit for Canada?

On a side note, I cannot cross the border without mentioning that I have a fiancé in the US; we crossed the border together last time, and they almost didn't let me in because I hadn't bought a return ticket (yeah, I know, facepalm). This time I'll buy one in advance though; I also have a flight ticket to Germany (which I showed them last time too, but oh well...), and I can give them the number of the attorney who is working on our case to file papers to get a fiancé visa so we can get married next winter. Do I have any chance at all to be allowed to enter again this month?

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As this question and answer state, since you're a resident of Canada, your VWP 90-day clock resets every time you return.

However, you have a much larger problem: since the US now knows you have a fiance in the US, and you were almost refused entry last time because of this, you will very likely be refused entry if you try to enter again on a visa waiver — they are now required to suspect that you're coming back to move to the US illegally. Random blog of someone else in pretty much exactly your situation, (claiming to) quote an immigration officer:

... from now on, you will have issues entering the US, and [proof of residence] will be a good thing to have on hand. Especially as we will be very suspicious that you are visiting your husband but not intending to move here. ... Also, the only reason why I’ve decided to grant you entry this time is because you already have your return flight booked. So make sure you do that next time as well. I am also going to let you know that from now on, you will be detained when you try and cross the border into the US. You are too much of a risk to stay here.

The safest option would be not to visit until you have that K1 fiance visa sorted out, but please talk to your immigration attorney and see what they have to say.

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