By Sometimes the best lessons come from the past. Until last summer (2025), I hadn’t been on a first date in almost a generation. Getting out of a relationship that was less than perfect, the thrill of realizing what it is like to engage with someone for whom you have “the feels” (as the kids now call it) was invigorating, if not downright intoxicating. The idea that a good-looking human wants to actually hold your hand, enjoys your company at dinner, laughs at your sometimes clever schtick and might want to even kiss you (no joke, I went 15 years without a meaningful kiss) can be mind-boggling. With that said, modern dating isn’t easy by any measure and, unlike a bike, you don’t just hop back on and be back in the game. There is an adjustment period and, for audiophiles given the gift of relief from marital agony, we are prone to falling into some big pitfalls.
This is where Damone’s Five-Point Plan for picking up women comes into play – specifically Tip No. 5. Fast Times at Ridgemont High is as good a comedy as has ever been written (by Cameron Crowe) and it has 1980s musical and California lifestyle references everywhere. What to do when you really like a really cute woman like Stacey can be a problem, but with the help of sage advice and some strong musical influence, you are going to be in good shape. My only problem with Damone’s advice, “when it comes down to making out, whenever possible, put on Side One of Led Zeppelin IV,” is that when Rat actually puts on the tape, it’s “Kashmir,” which isn’t on Led Zeppelin IV. This is Damone’s strongest point of the five. I hate to be THAT GUY with the Hollywood continuity problems, but Damone’s point is still highly relevant nonetheless.
Making Playlists is Not as Tricky as it was in the 1980s and 1990s
At 52 years old and a single man living in West Los Angeles, I might be a little old for FutureAudiophile.com’s aspirational young target demographic. The good news is that with my modestly advanced age comes a little gray hair and enough audiophile experience to have made my fair share of mix tapes on a buddy’s dad’s Nakamichi Dragon cassette deck (learn more here). I’ve also tightened the spools on some Maxell tape using a pencil. I might have owned a head-cleaning kit for my mom’s 1984 Honda Accord head unit at one point in my teen years. Thankfully, none of those complexities are relevant these days, but there are new ones.
The last time that I was single was around September 11, 2001. In that era, mix tapes were a thing of the past, as a CD-R (for the kids – that’s a recordable Compact Disc, I know – mind blown …) was the way to be really cool. If you had the right combination of CD-Recorder hardware, musical software (iTunes was pretty rough back then), and perhaps access to Napster and/or LimeWire, you could whip up a very curated musical playlist for an evening with a desirable potential partner. Damone was right. Creating a sexy musical mood is a smart move, even if Side One of Led Zeppelin IV isn’t the exactly right call.
Today, you can talk to your phone via CarPlay and Spotify or Amazon Music or Qobuz or any number of other sources, and can craft a playlist that can set the tone for an evening. Gone is the need for hours and hours of hand-curating music for a date. If only I had gotten that message earlier.
Audiophiles Need to Carefully Select Their First Date Music
The audiophile challenge is to find music that is both fantastic and sets the right mood but also sounds great. Often, this gets a little musically geeky. Perhaps one might describe it as a little bit on the progressive side of things and, while I love me some progressive rock, this might not be the best choice for first date music. Allow me to give you an example …
Recently, I was on a date with a tall, Australian brunette who was, in effect, in charge of the aviation department for a well-known tech/entertainment company. On the way back from a very Pretty Woman moment in Santa Barbara where we went to see a polo match, we drove back to Los Angeles listening to some choice jams in my EV (aka: my computer/battery on wheels). I was going to show her how cool this audio guy with a fancy music degree can be. What could go wrong?
Now if any woman knew travel, it was this one, so a song about an airport should have been perfect, right? So, when “YYZ” from Rush came on to my playlist, I felt like I might have hit a jackpot. I mean every woman in the travel world knows that YYZ is the code for the Toronto Airport. Every woman has to love a showy, technically excellent instrumental about an airport. I saw in the playlist that the next song up was “The Lumberjack” by Jackyl, which features a chainsaw solo, but somehow I didn’t get that far with this musical experiment, as perhaps I had gotten a little too progressive for this lovely lady of Generation X. She asked for a new jam and eventually to turn the music down. Damone felt as much shame as I did.
Life Lesson: Never Pick a First Date Song with Lyrical Verses That Are Alphabetical
OK, I need some grace from people out there. I never cheated on my wife despite having plenty of reasons to do so. So, when I got back out there, my dating game was a little rusty. During one date with a lovely Harvard educated attorney, a smart, pretty blonde lady who worked for our government, making sure that underprivileged people didn’t get outright hosed by the wheels of justice, who also loves music, when “Elephant Talk” by King Crimson came on my phone’s random collection of tracks, it seemed like it might be better suited for a trip to the stereo store than one for a motel that rents rooms by the hour.
It is important to admit when you were wrong and what you have learned. What I learned is: even for a woman who loves music and has a law degree from Harvard, songs written in part by Robert Fripp that present verses that are arranged in alphabetical order might not be as sexy as I thought. Oh, it is fantastic for music students. It is absolutely a jam to play on some Rockports and CH Precision at Sunny Components, but in my world it was female-repellent. Her response was polite yet sinking. I don’t think I got past the B-verse when I realized the failings of my ways, and that I was going to need to up my musical game if I wanted to hang with premium perimenopausal ladies of Generation X.
It is a process, people, and as a Sixers fan, I know to “trust the process.”
Don’t Tell Me That You Expect Me to Listen to the Lyrics First!
As a guitarist, lyrics just get in the way of great work over six strings. So, when you play a song like “Every Breath You Take” by The Police, you’ve got a love song that is demographically relevant and you are all good? NO! You are anything but good. “Every Breath You Take” is a song about a stalker and women that date online are rightfully scared to encounter anything like this nightmare. So, I guess it is best to consider the lyrical content of your music before you pick a track. An alternative song that one might select is “Every Little Thing She Does Is Magic” (a better overall song, if you ask me) and is a far better choice when you are playing the role of the Audiophile DJ of Love. I learned that you are not just curating a mood as much as you are a message, thus I am forced to actually pay attention to lyrics. Ugh … I recommend you pivot to a clever story about something like how backstage at a show at The Hollywood Bowl, Sting taught you the subtle details of tantric sex but you haven’t had a chance to try out what you have learned as you are looking for just the right partner. Now that is a musically-charged pivot to the hoop.
Even If Your Date was Born in Sweden – Do Not Play Any Viking Music
As someone who has rescued/fostered 13 golden retrievers over the years, I want to get another one at a time when my life presents such an opportunity. I’ve even picked out a name for a male one: Yngwie (as in the guitar genius Yngwie J. Malmsteen). Now, for those who don’t know the musical catalog of Mr. Malmsteen, it can get a little colorful and perhaps a little flamboyant.
The idea that the faster you/one can play their guitar represents any modicum of anything that would attract a quality woman is, sadly, a very flawed concept, I have learned. I was on a one-and-done date with a 50-year-old model from Sweden who worked with all of the famous female models of the late 1980s and early 1990s, but somehow, when the opening verse of “I am a Viking” from the Marching Out album (buy at Amazon) came on my phone’s increasingly problematic playlist, she looked like she needed a Xanax (or three). I was able to pivot to a better jam from my phone, but this, too, was a learning experience for me. I’ve had more than my fair share of these musical learning experiences in the past year or so, it turns out.
So, What is the Secret to Making a Successful First Date Playlist?
Why are you asking me??? Wait, I am the one writing the article … OK – first off, do some pre-date qualification as if you are an excellent salesperson. Ask some good Dale Carnegie, people-centered questions like “what kind of music do you listen to?” Don’t just assume that they want to hear Phish covering “Purple Rain” with a vacuum cleaner solo. They will give you some clues and you can build from there.
