Valentine's Day was pretty darn close to Groundhog Day throughout the 80's (the Bill Murray classic): it was, for the most part, the same day every year.
It began with one of those ads in the New Haven Register - a declaration of love that either your significant other completely expected (and even demanded), or one that targeted an unsuspecting lady (or gentleman), who then promptly dodged you until Spring.
There was either a visit to Long's Florist, or an order placed via telephone for delivery. Delivery suggested you just might wind up being somebody some day.
Dinner was most likely at Captain Nicks in East Haven. Runners-Up include Captain's Galley, if you were a Westie, or maybe even The Charthouse or Rusty Scupper.
If the 80's were being kind there might've been a pit-stop at Paper Moon, a lingerie/head shop that not only survived an incredibly long amount of time but might've been in the strangest location ever - on the corner of a residential neighborhood, with an apartment upstairs, and the next closest business was a car dealership.
I feel like there were jaunts for duds at Poor Richard's, but I cannot seem to confirm that was the name of a popular clothing store in EH, and neighbor to Friendly's.
Then this all could have ended at the Milford Pub & Cinema, where the movie had been out for months but booze got served to dozens of underage couples, along with Ritz crackers and cheese platters that went for 18 bucks.