Little Details

My novel is set in an Anglo-Saxon-esque land with similar technology. I have a scene which includes a single man sailing a smallish ship. All I could find online and in the university library are Viking ships (wrong culture) and Sutton Hoo (way too big, too many oars!). This is the only picture I could find of an Anglo-Saxon ship of small size (compliments of Project Gutenberg).



My questions:
1. First- a practical sailing question! Would it be possible for a single man to sail this sort of thing, or do I need to invent a smaller boat or give him a helper?
2. The A-S word in Beowulf is usually “scip” and that’s with my mediocre Old English skills. Would “Scip” mean a small ship, a big ship, or should I be looking for a more specific word? (It’s a Germanic tongue, so, God knows, there are insanely specific words!).
3. Anyone run across any great sources specifically on Anglo-Saxon boats (not Viking!)?

Setting: New York City, present day

Searched: Various combinations of southern, south, manners, courtship -- but I think this is probably more of an opinion/experience thing.

Characters: My character is a man in his forties who currently lives in New York, but was born and raised in South Carolina. Let's call him Steve. Steve's best friend and sort-of love interest is Adam.

Situation: Only half-jokingly, Steve told Adam that he was going to court him/treat him like a lady in order to get into his pants.

As a twenty year old female from the Northeast,I realized too late that I haven't the foggiest idea as to how Steve would go about courting Adam and treating him like a lady. There are a few little things, of course, like opening doors and ordering for him at a restaurant, but I'm really at a loss as to what kind of things Steve could do for Adam. When Steve was growing up, what might his parents have taught him about being polite to girls, particularly when dating? What have you done to treat someone like a lady, or how has someone treated you that made you feel like a lady? What kind of Southern manners might Steve display that would seem perhaps slightly out of place in New York?

Edit: First, thanks so much for all your help! Second, I want to mention that I'm totally down with any suggestions that would fit better in the movies than in real life, because Steve is very likely to take his cues from film rather than reality.

I'm going to be running an RPG where players are going to be playing rugby. I read the wikipedia article, and did a google search on rugby.

Unfortunately, I never actually have seen a rugby game. For those who have seen or played, any details I should include? It probably won't be a big part of the game, but some details I can add would be appreciated.

Thanks.