Recently at an Upper West Side Chanukah party hosted by a Jewish outreach organization, where singles stood in tight cliques balancing paper plates of potato latkes and plastic cups of white wine, I observed a beautiful blonde in a simple black dress standing alone near one wall. When men were introduced to her by a friendly, connector-type guy, they would chat her up with animation, but throughout the course of the evening, not one man actually approached the young woman, whom I’ll call Leigh, on his own initiative.

At one point, I walked over and asked her what she thought of the event.

“It’s good to get out and meet people,” she said, explaining that as a doctoral student in psychology, she studies and works long hours and doesn’t have a great deal of time to socialize. Of the men, she said, “They seem nice, but the cute guys never talk to me unless they’re drunk.”

Reflecting on her statement, I started to wonder: how many of these men would probably love to go on a date with Leigh, but lack the confidence to approach her?

And how many of them, rather than asking her, then and there, about her interests, her goals, and what she might like to do on a date, will get her name (or ask someone at the party for it), go home, try to find her on Facebook or JDate, and initiate a ritual of sending messages that might (or might not), after several weeks, result in their asking her on a date (at 7pm, for drinks, not dinner)?

Are men increasingly reluctant to approach women in real life (as opposed to online) for purposes of dating?

Of course, many people meet online and fall in love. But today, when cruising JDate has replaced spotting a stranger across a crowded room, the text has replaced the phone call, the ‘Facebook like’ has replaced face-to-face flirtation, and drinks at the dinner hour has replaced dinner itself, has the mystique of courtship been lost?

I grew up on stories of old-fashioned romance. My parents, for instance, met in a shoe store after my father saw my mother and was so smitten that he badgered the salesman to find out who she was (after he spoke with her in person and she declined to give him her name). Because she came from a protective family, he had to find someone who knew my mother’s parents–a distant cousin, it turned out–whom he enlisted to call their house and vouch for him. Since the cousin reported my Dad was a great guy, my mother’s mother not only approved but also pushed my mother to date him (I’m glad my father pursued my mother decisively; otherwise I wouldn’t be here).

Many of us grew up hearing stories about how our parents met–in a coffee shop on Lexington Avenue one rainy afternoon, in line at Coney Island waiting to ride the Cyclone, or perhaps through friends on that blind date no one expected would turn into true love.

I can’t help but wonder how much of our current dating culture is likely to produce these kinds of stories.

Can any woman imagine telling her grandchildren, “When your grandfather and I were dating, we exchanged text messages for several weeks and then he took me out for drinks … It had been a long day at work, and I was really hungry. By the time he ordered the second round I was nearly falling off the bar stool, but when our eyes met and he suggested we split an appetizer, I felt like he just might be The One. He texted me a few days later, and since I wasn’t sure if he was that into me, I ran out to get a slice of pizza first (since he’d asked me for drinks at 7pm …)”

Jewish singles with whom I spoke for this column were divided about whether online dating – and technology more generally – are killing romance. Generally, twentysomething singles seemed more positive, but even they aren’t crazy about it.

Some, for instance, find it stilted.

“With online dating, it seems like there’s this ‘structure,’” said Jessica, 27, a Manhattan marketer. (Name has been changed). “First date drinks, then on the second date they try to make out with you, and on the third date they want to start hooking up.”

Jessica, who is pretty and confident, has decided to take a “detox” break from online dating and dating in general.

“Most of the guys who have asked me out in person are over 35,” she said.

(I can’t help but wonder: Where are the guys her age? Sitting around at home cruising Facebook and JDate in their underwear? Getting drunk and looking for Ms. Right Now, as opposed to Ms. Right? To paraphrase Vince Vaughn's character in "Wedding Crashers," they're young, but they're not THAT young. By the late twenties, shouldn't they have the social skills to ask a woman out, face-to-face, for dinner, not just to "hang out?")

Overall, Jessica believes that in the era of online dating, “There’s a different getting-to-know-you process. It’s tougher. It delays things and is more confusing. But I think a guy will step up when it’s real.”

Of course, dating – like any kind of relationship building – happens in stages, and no one who invests everything up front is smart.

But unwillingness to risk one’s ego by picking up the phone, or spending a few dollars and hours to put on your best face and make it clear you are interested in getting to know someone, undermines any real opportunities to connect.

Just ask Leigh and Jessica.