The Gaming Scholar

You are re-living your college days. Right in the heart of New York, you find the perfect outdoor location that has chilled winds and gaming arcades near a food street. You both become competitive college students, loaded with video games and flirty tendencies. The roles are divided - she's the queen of the gaming world who can't be defeated, and he's the competitor who has the charm to disrupt her gameplay. As the cold wind blows, you jump from one game to another, high on the challenge and the tantalizing whispers exchanged in-between. The chill of November is forgotten in the warmth of your connection and teasing glances.
As you compete, you can't seem to keep your eyes off each other. Getting absorbed into each other’s life, you exchange steamy looks, playfully arguing and debating over games. The flirty conversations turn into intriguing talks fueling the intimacy.
Your senses are heightened, the spark of competition is ignited with passionate advances, turning the cold November day into an afternoon filled with thrilling intensity and intimacy.

The first thing you would need to prepare is your outfits. Go for outfits that truly represent a flirty college student vibe. Think about representing your favorite college team or simple yet stylish collegiate outfits. The female partner can outfit in a 'Sexy adult school girl' uniform, and the male partner can don a 'Sexy adult prep schoolboy' attire.
Secondly, familiarize yourself with several video games, choose a mix of old classics like Pacman or Space invaders, and new ones like Fortnite or Overwatch. Learning the basics will make the scenario more realistic and fun. You could even do a little practice prior to the date to spice up the competition.
Finally, book an outdoor setting preferably near a food street and gaming arcade or arrange an outdoor gaming setup in your backyard, complete with a space heater to keep you warm on a cool November day. Make sure the essentials like game stations and seating arrangements are set up before your encounter begins.

Ensure that you research and agree on the kind of food that you will eat during the date to avoid any discomfort later. It could be NY's famous hotdogs or elegant sushi, depending on your mood.
Flirting plays a vital role in this scenario, so be creative with your words. Use gaming language to tease each other, such as references to leading the game or about resetting the scores, to spice up the scenario.
Lastly, set the mood with your favorite music playing in the background and let the ambiance help in enhancing the emotional connection during your roleplay. Keeping your outdoor gaming setting well-lit and warm will only add to the overall winter role-play experience.