The dream takes place in Florida, a place close to home and popular vacation spot; a place to go to relax. The beach is also calm and relaxing, the restaurant is informal. The night is also a time of personal socializing, parties, and sex.
The name of the restaurant, as you guessed, is sexual. Pineapples being juicy, tall, a bit tough on the outside, and good for making semen taste pleasant. They're also big compared to most fruit, and a not uncommon tropical symbol. Willy's is a bit obvious. What's more interesting is why your mind chose it rather than a more sexual word. I think it continues on the theme of relaxation. Willy is a fun euphemism for penis used among children and the word, in an onomatopoeic sense, is flaccid. Willys are what you see when changing diapers or cracking jokes. Cocks are what you take to bed.
You're at the bar, a place of high social interaction and open conversation. Hotmilf posts frequently and she's fun. Her avatar, while humorous, also had a dash of danger to it. Seeing that little wiener skewered makes you wonder. I think you wanted to ask her the question just because you did but either felt you couldn't ask the question here or just kept simply forgetting.
burns1de also posts frequently and he's very open about himself. They both come across as relaxed, confident, fun people to know. The sexy alligator, could apply to either of them but I think it applies to you because (correct me if I'm wrong) you drank it. Alligators are tough, have huge mouths, and like to devour things. If they're sexy as well, then the alligator springs when least expected. This indicates you are attracted to them not only as friends, but sexually as well. Interesting then that they're both straight and you felt you could only communicate that attraction in an atmosphere of extremely casual, relaxed, openness. Someplace, "not at home," on vacation perhaps where we are freer than we usually are since we are away from those who know us.