Yes, always keep water in the cup. I would also move it closer to the window. The brightest light you can get without being in sun. You can put a little water in the pups' funnels too.
The life cycle of bromeliads is that after the mother plant pups it will eventually die. The pups should be at least 1/3 the size of the mother before you remove them. I keep them on the mother as long as possible.

Did it have a flower stalk or was the flower down in the funnel?

Ok thank you very much! So the issue with the light situation is that the west windows are in an awkward position and can't really have anything in front of them because they are right by a stairwell. I have moved most of my plants into my room because it is warmer, however i only have one north facing window. I think a grow light is in the near future for me. Should I wait to remove the pups till spring or do it whenever they are ready? i have one that is definitely ready but i didn't want to plant it and then have it die because of improper conditions.
I beleive the flower was down in the cone. All that remained when I got it was the remnants of the flower, no petals, but it was in the funnel.