I'm one of those people who pays every single bill via the automatic monthly withdrawal feature offered through online banking.

Last week I renewed a prescription on the CVS online pharmacy interface. Every time I drive somewhere new, I Google Map the directions, Street View the location to assess parking, and Sigalert the recommended route to see where traffic is heaviest.

We are living in a digital world, and I am a digital girl.

So when the idea of Skype-meeting my new boyfriend's parents first came up, I thought, Yes. Simple and efficient. We each live across the country from our respective families, both of whom were growing like parents can grow when waiting to conduct the first-impression interview. ("The pictures are good, but maybe you could, oh I don't know, send a video ...?" mine said. "It's just hard to get a sense of his entire personality from the photos, you know?")

It was my boyfriend who came up with the plan.

"I'll just arrange to Skype with them and you can stick your head in to say hello," he suggested like the rational man he is.

"OK, sure," I replied. "I can do that."

It's important at this point to mention that I have never "met the parents" in an adult relationship. (High school has got to be disqualified at this point.) I didn't date anyone in college and didn't date anyone long enough post-college to warrant the meeting-the-fam milestone.

It is more important to mention that the gravity of this fact did not hit me until 30 seconds before the Skype session began.

So, issue number one: OMG-this-is-a-big-life-moment nerves. These came in the form of an I'm-marking-a-massive-life-milestone lump in my throat that for some reason emerged as an uncontrollable smile that was half-I'm-so-happy-we-made-it-to-this-point and half-oh-my-God-what-happens-now-that-we're-at-this-point?! It can't have been pretty.

In general you want to go into any significant first-impression moment with a clear and focused mind. I know this from the dozens of job interviews, business meetings and networking events I've attended graduating college with a degree in communications. Offer a firm handshake. Speak slowly. Make direct eye contact. Try not to slip into your nervous behaviors (mine: Borscht Belt jokes, complete with accent).

Issues numbers two through four: You can't shake hands over the Internet; voice transfer on Skype can be patchy; and webcams make eye contact weird (you have to look directly into the camera to make eye contact but then you can't see the people you're talking to). That, plus I had been told this specific audience never met a Catskills comic they didn't like.

Also, the interface offered zero opportunity to divert attention from nervousness with a thank-you-for-having-me-at-your-home gift. Lovely candle covers sweaty palms in the first-impression tango.

My lovely boyfriend R. set up the Skype while I tried to determine if a low side pony would look good or bizarre on my head in a 5-by-5-inch box. Forget applying makeup that would properly translate on the computer screen (note to the glossies: some of us could use that "how to" article).

So, we're at seven issues in just as many minutes. I should have been grateful that things like footwear, skirt length and proper table manners didn't apply, but I was too focused on deciding whether I would wave or just say hello when the intro occurred. Or maybe open with a joke and mime a handshake?

Before I could decide Mr. and Mrs. R. were 10 inches from my face. One of them went with the wave, so I followed suit.

See, the thing I've now realized about a front door is that you can hear it start to open and then properly prepare your face to be seen when the person on the other side appears. Skype offers no such countdown. One second you're rehearsing the seemingly infinite ways to say "nice to meet you" (in your head, of course) and the next you're face to face (kinda).

Barring some technical difficulties -- sometimes Skype just freezes the picture, meaning the people on the other end see your face locked in whatever look it was just making; preparing for that potential scenario was a minefield -- we had a lovely introduction. Mr. and Mrs. R were as charming as their son and expertly managed a conversation that was equal parts catching up with him and getting to know his new girlfriend.

Its length was the equivalent of that 15-minute window before the waiter comes and you say, "Oh, ha ha, we've been talking so much we haven't even had a chance to look at the menu!" and I spent at least half of it consumed with just how close I should sit to R to both fit in the frame and not seem as though I was melted into his lap. But I am proud to say that I made it through with only one Uncle Mort–style zinger (which I'm told was a huge hit with Mrs. R).

And with that I've crossed one major milestone off the adult-relationship list. Of course, when people ask I say, "I said hello to R's parents over Skype." We won't officially have met until I give them a hug and they can see my entire outfit.

Jessie Rosen is a frequent Lemondrop contributor and financial genius /television superstar, having covered the 20-something scene for us before. She writes the blog 20-Nothings, an account of getting by from 2-0 to 3-0 with minimal wind resistance.
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