Ask a woman out on a date. What a concept! This means, don’t just say, "Oh, by the way, I’m going to a party Saturday night, want to come?" This also means, don’t send an e-mail (or worse, a text message) saying, "Hey, wanna do coffee sometime?" It means phone her or say to her in person, very specifically: "I’d love to take you out. What are you doing tomorrow?"
Choose a specific venue for the date. I hate it when guys ask, with uncertainty, "So what do you want to do?" I know sometimes men like to let women feel in control, but I like to see the first date as a dance — let the man take the lead. Don’t choose an ordinary venue — like Coffee Bean or Starbucks. Surprise her with a new cafe designed with a funky concept or a tapas bar, for instance.
If the date goes well, end it with a specific conclusion, not just "We’ll be in touch." Don’t rely on the woman to make the next move. Show her that you are confident by saying that you are looking forward to seeing her again — if indeed you are — and that you will call her in the next day or two.
Initiate contact within two days after the date. Call or e-mail — but don’t text! Tell her how much you enjoyed the date — but be specific about what you enjoyed —her ideas on the elections, her passion for Israel, etc. Don’t offer corny compliments about her outfit or her eyes. Arrange the next date over the phone without letting too much time pass so that she doesn’t have too much time to doubt you.
Invest in her interests, but sincerely. There is nothing more attractive than a man who gets to know the heart of a woman by investigating what is important to her. For example, if she raves about a particular movie, look it up on Google. If she mentions an artist that she loves, offer to take her to a local museum showcasing his/her work. I once told my date how much I was influenced by "The Fountainhead." He went out the next day and bought it. He read it within a week, enjoyed it sincerely, and indulged me in lengthy discussions about the book’s ideas. He got me.
Once you graduate beyond coffee or drinks, plan creative dates. Take her to a new art gallery, a hike into the mountains, a bike ride at the beach. Show that she’s special enough for you to put thought into the date.
Don’t pressure her for sex — ever. A man can innocently request a kiss, but, ideally, he should let the woman take the lead when it comes to sexual play. This restraint proves a man is after her soul, not just her body. You can definitely initiate affection — like handholding and cuddles. Most women love that.
In the beginning, don’t bug her or call her too often. Better to offer a few intelligent statements about her or the date rather than hammering her with one-line text messages that say generic things like "Have a great day" or "Thinking of you." Try to avoid "biting," "poking" or "teasing" her via Facebook. All this can come across as phony or desperate. Unless she is really insecure and needs this fawning, give her space.