i went in for the kiss...

A video on YouTube. In Lifestyle, a Krater category.

Summary by Krater

A creator takes his roommate on a series of romantic dates in New York City, including cafes, the Edge observation deck, and painting portraits, culminating in a rooftop proposal.

From the video

Answers: How do I plan a romantic date in New York City?

dating in New York City
painting portraits
The Edge observation deck
rooftop proposal

What it concludes

The creator decided to propose to his roommate Ashley on a rooftop in New York City.

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Titles and thumbnails from YouTube. Krater isn't affiliated with, endorsed by or sponsored by YouTube or Google.