Keira writes in with her essay prepared with the single, gadget-obsessed male in mind. It's titled "On Gentlemen Giving iPods as Gifts—Keira's Primer on the Art of Seduction."
She believes that women do like iPods, but that they do not always make wise gifts, and subsequently, giving one won't do much to improve your odds of getting laid, unless...
... you do it right.
Although it might make you seem as if you're well off enough to afford her such a gift—and don't even think about giving her a shuffle—it might also present the possibility that you're "lemming-like" in your "willingness to follow trends."
The somewhat sterile modern lines and minimalist stylings of Apple products also give your Dream Girl no clue as to what precisely it is you mean with your gift— Is this a romantic gesture, an invitation to marriage, an abject apology, offer of sincere friendship, or did you merely receive an extra for your birthday? The blank iPod facade offers no answers. Surely it is now clear to you that the problem with giving the iPod as a gift is that you must personalize it in some way in order for it to be effective as a woo.
I blockquote in great quantity because it couldn't be said better. Onward.
Should you engrave then? No!
If you could write effectively and beautifully (let alone engraving-worthily), you would have no need to shower gifts upon her in order to gain a lady's favor. They would be giving iPods to you.
Expressing your Eternal Love on the back of a fancy radio that will (at best) last a few years is not only highly inappropriate as a gesture, it is also trashy, like carving your names into the bark of a tree, or getting a tattoo.
If you think about it, what you are trying to do is make a better impression; were her immediate impressions of you favorable, you needn't bother with trinkets, just honest conversation and proficiency at the Intimate Arts. What a woman will seek in examining the contents of the iPod you give her is some knowledge of your Inner Life, described through your tastes, which might help compensate for your Outer Troll. Therefore, consider this as a very large Mix Tape.
Click through to Keira's site to read how to—and how not—to make such a mix tape.
On Gentlemen Giving iPods as Gifts [Prides and Prejudices]