Start with the thing that actually goes wrong here. This is a hamlet of single-family houses on a street grid — no lobby, no doorman, no concierge, no front desk — which means every classic romance delivery script fails. There is nobody to hand the flowers to who is not the person you are hiding them from, and there is no back room to stash them in. A surprise in 11801 therefore has to be engineered rather than ordered. Three things work. One, send to the recipient's workplace, where a reception desk does the job a doorman would. Two, send to a named neighbour or a parent's house on the next block and collect later. Three, give up on the surprise and pay for a timed window in the evening so the flowers arrive while you are both there, which is a better night than a bouquet found on a step. What does not work is a daytime porch drop to a house where the other person might be home sick.
The second thing that goes wrong is February. Long Island's cold is not dramatic but it is patient, and roses are the least forgiving thing a florist sends. An arrangement that sits twenty minutes on a concrete step in a Hicksville January or February — or rides in the back of a van with the door opening every four minutes on a Valentine's route — arrives with its outer petals bruised and its stems shocked. Every shop on this grid knows it and they route accordingly, but they can only do so much: the fix is on your side of the order. Give a window when somebody is actually indoors, give a mobile number the driver can call from the driveway, and say if there is a side door under an overhang or an unlocked storm door. On a cold day the side door under the overhang is not a convenience, it is the difference between flowers that open and flowers that do not.
For a night out, the geography runs north and west. The dinner arc Hicksville couples actually drive is Roslyn and Roslyn Heights — Kotobuki, Mim's — and Westbury, where Cafe Baci sits; add Old Westbury Gardens and the Planting Fields at Coe Hall in Oyster Bay for the daylight version of the same evening, both within about eight miles and both better backdrops than any restaurant. Closer to home, the South Broadway restaurant row through Hicksville is the densest South Asian dining strip on Long Island and it is where a very large share of the hamlet's date nights happen. Phone ahead if anything is going to a table. A Nassau dining room will usually take custody of an arrangement and produce it at the right moment, but it needs to know which booking it belongs to, and a two-top has no surface to spare. For an overnight, the closest beds are the Hilton Long Island at 598 Broadhollow Road and the Marriott at 1350 Walt Whitman Road, both in Melville, with The Garden City Hotel on Seventh Street as the grander option to the southwest. Hotels need the name the room is booked under, the check-in date, a phone, and a clear instruction that the flowers belong upstairs and not behind the desk.