Hi Tom’s son,
First, I’m well removed from those days of yore when I was a novice dater. I’m 30. I’m not elderly, but I’m sure to you I’m more like your dad than your brother. But I have a brother who’s 15, so I can kind of sort of maybe a little relate.
Girls always appreciate politeness. Remember this: She is not your best friend, although she may be someday. You don’t treat her like she’s “one of the guys.” You might know this already. You’re saying right now, “Well, duh.” Well duh is right!
When you’re driving her somewhere, open all doors. You don’t have to have to make a big display of your chivalry, because she might take that the wrong way and think you’re patronizing her. Look out for her, not because she’s female but because by definition a date means you’re treating her like a guest. So hold open the door; just don’t bow.
When you’re at a restaurant, let her order first, and let her order whatever she wants. You don’t have to tell her this, but don’t make the mistake of saying, “No, you can’t have the filet mignon. What am I, made of money?” If you want to date her, you should already have an idea of how sensitive to you she’ll be. Is she the kind of girl who will order a lot of things from the menu? If so, then don’t date her. You’ll regret it, trust me.
Also, hold her chair for her when she sits down. Again, you don’t have to go overboard, but just do it out of politeness. Girls love politeness, and she’ll be suitably impressed.
Remember your manners when you’re dining. Pretend you’re at someone else’s house (which you are, of course). Elbows off the table. Don’t scratch. Smile as much as you can, but don’t force one. If you need to use the restroom, excuse yourself politely. Make as much conversation as you can, but don’t discuss only yourself. Find out about her. Girls love to talk about themselves.
When paying, pay it all - unless you already know upfront that you’re splitting the tab. In most cases, you wouldn’t - and you should always assume you’re paying the bill unless it’s been explicitly discussed otherwise.
Girls (and women, as you’ll see when you get older) really appreciate honesty, politeness, kindness, intelligence, and a sense of humor. If you can be a good conversationalist and can treat her with respect, you’ll have a second date for sure.