Sneak onto? Why not just go to a rooftop bar? Lol.

1 Hotel Brooklyn Bridge has a rooftop with nice views of the Brooklyn Bridge / Statue of Liberty / Manhattan. I believe it’s call Harriet’s rooftop. Drinks are on pricer side but definitely a place to impress someone.

>a little thrill involved

Maybe the OP wants to get the adrenaline pumping to 1) make the experience more memorial, and 2) because the mind might confuse excitement for infatuation

I like Jimmy in Soho. Great rooftop views. Cocktails. Even a pool to jump into with your date

Plus the implication

But the thing is she's not gonna say "no", she would never say "no" because of the implication.

If you want to sneak onto a roof, take your pick of buildings. Find one with a nice view, ring all the buzzers until someone buzzes you in, and head to the roof. Just make sure your date is holding enough cash for bail and you set up a meeting place for when they release you from holding.

Plenty of nice rooftop bars in the city though. Maybe do that.

Maybe afterward you can take her back to your parents' apartment on the handlebars of your bike!

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