In my eyes, the whole dating game is a bit like doing The Hokey Pokey. Ultimately, you just want to meet someone who makes you think, "That's what it's all about!" (whoa, the Hokey Pokeyyy...). But until that point, you go through the motions of the Dating Dance. At times it's fun, even exhilarating. At other times you'd rather lop off a limb than participate in any more rounds of this bizarre social ritual.
Obviously how you perceive a romantic overture depends on whether or not you like the person. If someone who warms your heart-cockles remembers your favorite song (which you mentioned in passing 6 months earlier), it's sweet. If someone who irks you devotes themselves to learning the ukulele so they can Manic Pixie Dream Boy serenade you, it's creepy. The adorable/deplorable line is pretty much subjective.
That said, there are certain things you can do to set a date up for success:
Classic is good, quirky is better
Show your whimsical side by taking your date to an interesting museum exhibit, chocolate factory tour or arboretum. Reject flowers in favor of a thoughtful gift; much like Natalie Portman receiving a bouquet of carrots in No Strings Attached, my friend Freya was won over by her now-boyfriend Mike presenting her with a first date avocado. Of course, you may prefer to stick to a tried and tested "perfect date" formula. If so, heed the words of the kids interviewed by Charlyne Yi in Paper Heart:
"Dinner and a movie. But before that you'll watch the sunset on the beach. And the restaurant that you will go to is a French Riviera restaurant that only sells seafood. That's a good date."
"You need to take somebody to Applebee's and get them hot wings."
Compliment your date, but not on their looks
Besides a perfunctory, "Wow, you look great!" I don't think you should comment on someone's appearance until you've been on a few dates. You're not into the superficial, right? Personally, if you laugh at my jokes and tell me I'm funny/interesting/weird-but-not-in-a-terrible-way I will blush like a schoolgirl and start mentally designing monogrammed couples stationery. If you tell me I look like I work out or "have beautiful soft hands like a Sylvannian rabbit" I will vomit on your face.
Be polite to waitstaff
Saying "thank you" is polite. Thunderously clapping the weary string-bean of a waiter on the back and calling him "Brosef" is patronizing.
Pursue interesting conversation
Hobbies, films and books are usually good conversational kindling. But maybe don't refer to Nacho Libre as "the best film of all time." Or at least don't insist on giving a 92-minute blow-by-blow of the movie in a stilted Spanish accent with one-man renditions of the wrestling scenes. Also, learn to respond appropriately. Hometowns are a good talking point, but if your date says she's from Canberra, don't trace a map of Australia on her torso and ask her to point out where the city is. Also, don't brag about being a blood donor.
Initiate a light touch (if the mood is right)
Like compost, the best kind of contact is organic. Nothing quite dampens the mood like stiltedly asking your date, "Can I put my arm around you?" On the other hand, you hardly want to go in for a shoulder clasp only to have them freeze, then slowly extricate themselves like a tapeworm from an intestinal tract. A good move is to lightly brush their hand and see how they react. If they give an involuntary shudder, recoil like a snail being pelted with Epsom salt, and look like they're going to sick up, hold your horses.
Make an effort with your appearance
If your t-shirt was the product of mailing in 6 cereal box coupons or was fired out of a mall-cannon, it's probably low-grade slub cotton, not date material.
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