A man living with a group of friends in New York City decides to ask his roommate Ashley out on a date. Despite initial concerns from his roommates about the potential awkwardness and complications of dating a roommate, he decides to go through with it. The date goes well, and they have a fun time together. However, he has a surprise planned for her - a helicopter ride, which she has never been on before. The video ends with the man reflecting on the date and the potential challenges of navigating a romantic relationship with a roommate, but feeling optimistic and excited about the possibilities.
Here are the key facts extracted from the text:
1. The narrator moved to New York City about a month ago with a group of friends.
2. The narrator has been thinking of asking their roommate Ashley out on a date.
3. The narrator is concerned about the potential consequences of asking Ashley out, as they are roommates and have 10 months left on their lease.
4. The narrator asks their other roommates, Elliot and Marie, for permission to ask Ashley out.
5. Elliot and Marie give their permission and offer advice on what to do on the date.
6. The narrator plans to take Ashley to a rooftop bar and get her a drink.
7. The narrator buys Ashley flowers, despite not knowing if she likes them.
8. The narrator and Ashley go on their date, which includes going to The Boathouse and ice skating.
9. The narrator and Ashley have a good time on their date and share a kiss on the cheek.
10. The narrator plans a surprise for Ashley, which is revealed to be a helicopter ride.
11. The narrator and Ashley go on the helicopter ride and enjoy the experience.
12. The narrator and Ashley are now in a relationship, despite being roommates.