..don't be afraid of a little self deprecating humor; i.e., don't take yourself so seriously. Tell her you were a carney in your younger days...every woman was once a teenager who fantasized about doing the skinny young guy with the tatoos in the straw cowboy hat who ran the tilt-a-whirl.
...always have an extra toothbrush or two (new, stoopid) in your medicine cabinet. Have a fresh bar of soap in the shower and on the vanity. Ditto fresh roll of tp. If she is going to take a shower lay out the towels so she doesn't have to snoop. Have a guest bath robe.
...keep a box of tampons (the variety pack with the three different sizes) in the back of your linen closet. This serves many purposes. She may think you're the ultimate boy scout. It keeps you from making a trek to the c-store at 4 a.m. and ultimately buying the wrong product ("Dammit, they're all in a blue box"). Make her wonder....act as if every male keeps a supply. If she should ask you why you have a box of tampons, tell her they're the best disposable shoe polish applicators known to man.
...learn to give good bed; i.e., invest in a feather bed, 4 down pillows, a down comforter and high thread count sheets. Only 100% cotton. Makes em never want to leave on sunday morning...which may not always be a good thing. Good bed=good head.
...sleep on the wet spot...at least during the first two over nighters.
...down play your professional/financial accomplishments.
....never date a woman with mispelled tatoos.
....always have a bottle of inexpensive champagne and at least frozen OJ in the fridge. Even rotgut mimosa's will cheer 'em up in the morning. Toasted plain bagels and cream cheese with some fresh fruit on the side makes a great brunch over the sunday paper...even if you're alone since she slipped out while you were sleeping. Real cloth napkins are a nice touch.
...leave a clean but wrinkled white dress shirt somewhere convenient in your bed room. Nothing like a sleepy eyed woman walking around your place with nothing but that on in the morning.
...rid your cave of all pictures/memorabilia of past relationships. Even if it was the best picture you've ever taken while skiing in Vail 8 years ago with the woman who broke your heart and bank account.
...no matter how great the first few dates are going, hold back a little. Fer chrissakes don't tell her every thing about yourself and your past. Be a little cautious and mysterious.
...Dating in middle age is both wonderful and problematic because the age span of available women is so broad. 22 to 52+ is likely available. I've found if they're between 22 and 32 and the wanna date me they're looking for a daddy or a sugar daddy and I don't wanna be either. If they're between 32 and 42 they've usually just gotten out of a marriage or LTR and there is a certain amount of anger towards men: either their ex was a jerk or abusive or delinquent on child support or their lawyer screwed them over...lotta anger. And if they're 32-42 and haven't been in a marriage or a LTR there's likely a reason...and it usually ain't good. Between 42 and 52+, they've likely come to grips with their hatred of men, got the kids pretty much raised and have establish themselves professionally and are interesting and independent. As a result they set their expectations so high of who they "should" be dating that you'll never be able to live up to their ideal. So....you're screwed no matter which way you go.
But it beats the hell outta eating cheetos, watching porn and wonderin' why your johnson has turned orange.